Angie, My Mature Secretary

"Ted, can I talk to you real quick?" The interruption wasn't welcomed. It was past 6:00pm and I was trying to finish up an email to a customer so I could get out of the office for the night. But Angie had this concerned look on her face and being the helpful co-worker I try to be, "sure, Angie, what's up?"

"You know that overnight package you wanted me to get out tonight? Well, I never made it to the drop-box so it didn't go out."

I know my facial expression gave the impression it was a bigger deal than it was. And in reality, it wasn't a big deal. Getting it delivered the next day was a nice to have, not a need to have. It was an annoyance, though. Angie had been with us for 3 years now and she just wasn't getting it. In some respects, it didn't surprise me. Angie was in her mid-50's and had been a stay at home mother while raising her kids and then a homemaker after that. She was late to the scene insofar as office skills, computer technology and so forth. She was smart and had good people skills, but technically she was at a big disadvantage. She did have a close personal friendship with Tanya in our office, though, and it was Tanya who convinced us that Angie would be great to fill the open admin assistant position we had. Tanya was about the same age and was a great worker. In fact she could have handled the extra duties of the open admin position but had no desire to do it because there was no extra money in it for her. Tanya was good but no dummy so she pushed for filling the open position. And she had just the right person for it. Angie was a friend of hers, had just completed administrative assistant courses at the local community college and was in need of a job. Her husband was steadily employed for years but lost his job and then was floating from one place to another for years. According to Tanya he was a bit lazy and when he lost his steady gig, no subsequent employers wanted to drag his ass around. Angie needed the work to not only help support herself and her husband but also to gain some independence from him. Tanya said he wasn't physically abusive but was verbally demeaning to her. So there she found herself, in her mid 50's and married to an intermittently employed man who she wouldn't care less if he walked out except for the fact she needed a roof over her head and food in the cupboards.

For an older woman, Angie was very attractive. She kept her brown hair short and conservative in style, had a nice smile to go with her hazel eyes and a relatively fit if curvaceous figure. There were times I'd take the opportunity to sneak a peak at her breasts when given the chance and when she wore a particular form fitting skirt, I did have the desire to throw her over my lap and spank her round bottom. In that passing fantasy, the spanking usually involved one of her screw-ups like we had today.

"Really, Angie? We had told Pete we'd get that out to him for tomorrow." As I made that last statement, I gave her the raised eyebrows, open eyes look that says, "we've gone over this before, this is important stuff, blah, blah, blah." It was my best attempt at playing manager and I had my doubts about how well I was pulling it off. Angie and I work in a relatively small office and we were the last ones there so I figured I'd get in some practice time.

"I know, I'm really, really, really sorry." I could see she was really sincere and very concerned. While Angie worked for me, she also worked for the others in the office and I wasn't her direct manager. That was Lisa, and Angie's mistakes were starting to get on Lisa's nerves. Lisa was in her 30's about the same age as me and tough with a chip on her shoulder. She was giving Angie a chance because she wanted to give another woman a chance, as long as that woman was not a threat to her position of power in the office. But the talk around the office was that Angie had worked through her grace period and was starting to be given the ultimatum to either shape up or move on. The pressure was there and as Angie stood before me, I could see in her eyes that she thought this could be the straw that broke the camel's back.

"Is there anything I could do? I'll do anything to make this right, just let me know. Lisa will kill me if she finds out about this. There's got to be something I can do. Really, I'll do anything." I don't know what Angie was suggesting with her comment but hearing the magic words "I'll do anything" awoke the devil in me. He popped up on my left side saying, "she seems really vulnerable right now. You've been wanting to massage her breasts and I bet you could get away with that without any questions. She'd probably suck your cock of pushed." I don't know how long I sat there contemplating her offer but the thought of putting my hands on her breasts and exposing my hard cock to her sent the blood rushing away from my brain straight to my penis, which was starting to bulge in my pants. An angel on my right side said something about losing my job and some other stuff, but the devil seemed to have me pretty convinced Angie wasn't going to say anything. As I got up from my chair, the next words out of my mouth were either going to be consolatory or change Angie's and my relationship forever.

"Angie, those papers had to go out tonight. Pete needs them for tomorrow. The shit's going to hit the fan when I call him to let him know they're not going to be there. There's nothing we can do to get them there any sooner. I'll have to deal with him tomorrow and see what I can do." The look of despair and concern overcame her face. I stepped forward and put my left hand on the small of Angie's back and my right hand on her left forearm. "You really want to make this right, Angie?" Our physical contact prior to this had been limited to that of normal co-workers so the look of surprise on her face wasn't all that surprising as she nodded with some confusion, "listen, I'll try to make this go away with Pete and won't say anything to Lisa...," as I said this I slid my right hand down to her left wrist and firmed up my grip, pulling her hand to the bulge in my pants as I slid my left hand down from the small of her back to the top of her ass pressing my middle fingers between her cheeks. I leaned into her bringing my mouth to her right ear,..."but I need you to do something for me." I could feel her body stiffen a bit as I started to kiss her neck and slide her hand over my pants along my hard cock. I pulled my face around to hers as she stared at me and kissed her lips with nothing coming back.

I started to feel I may have miscalculated things a bit and rather than fall back, I decided to press forward, "I'm going to take a lot of heat tomorrow...now unzip my pants and pull out my cock." Angie had that scared look of "what should I do" all over her face. I pulled her close again and started kissing her neck now putting both my hands on her ass running them both down to the back of her thighs and back up again running my fingers between her cheeks. I'm not sure if her gasp was brought on by pleasure or because she had stopped breathing, but I looked at her again with a direct look and a firm voice like a father talking to a child and said, "Angie, unzip my pants and pull out my cock. You've gotten it hard and I want you to hold it and stroke it for me." She continued to have a look on her face that was difficult to gauge exactly what she was thinking as she moved her hand to my zipper and lowered it. She eased herself down in one of the guest chairs in my cubicle and slid her left hand into the open zipper running in the direction of my erection. She rubbed it back and forth a couple of times before removing her hand and looking up at me with her beautiful eyes and what as best I could describe as an obedient look on her face as she undid my belt. Releasing my pants button, they fell to the floor. She lifted up the shirt tails exposing my erection in my underwear, she pressed against it hard rubbing it from the base to the tip. As she did this, I unbuttoned my shirt dropping it on the floor behind me.

Standing there in my underwear with my pants around my ankles, Angie's expression transitioned from obedient to having a slight smile as she slipped her fingers into the elastic waistband of my shorts pulling them down around my thighs. The waistband had kept my erection half way between horizontal and vertical and when Angie pulled my shorts down, it sprung my cock up like a catapult. I'm not sure if it was this or seeing my cock for the first time that made Angie giggle. Being fully exposed before her and her head at the same level as my cock was a big turn on to me as she wrapped her left hand it and began to stroke back and forth. "That feels good. Keep stroking it just like that."

Angie had nice soft hands and she knew how to stroke a man's cock. She was slow and rhythmic and would gently caress my balls with her right hand. As I looked down at her I'd catch her gaze floating between my cock and my face to confirm my continuing approval. As I gazed down at her and her luscious curves, I saw that her nipples were poking through her blouse. I reached down with both hands to start unbuttoning her blouse. I got only the top two buttons before I was interrupting Angie's rhythm and she stood up and finished the buttons for me, removing her blouse and then her bra. As her breasts were bared to me, Angie's look became what seemed embarrased or nervous making me think she might have been insecure about her body. But her breasts were beautiful for a 50 something woman and I gently ran my hands underneath and over her nipples as I closed my hands over them. She seemed to like this and she leaned forward so I could kiss her.

Separating from our kiss, Angie sat back down and began stroking my cock again. But her expression had changed as she started to breathe more heavily through her mouth and her grip became more firm as she started to stroke my cock in almost of a milking fashion, squeezing her fingers starting from her pinky up to her index finger and thumb. It made me moan out loud and she moaned back in response and I realized I was losing control of the situation. Part of me wanted to cum all over Angie and the other part wanted this to last all night, and I knew which part would win. My breathing became very heavy and fast and I began to moan louder, "oh, that's it, yeah, yeah...." Angie's stroke became very firm and fast and I knew that I didn't have much longer. And Angie knew it as well. She wrapped her right hand around the inside of my left thigh and held me tight to her. I could feel my balls begin to contract and my load of cum rising in my cock. I had hit the point of no return where I knew it was pointless in trying to stop myself from coming. "I'm going to cum!" Angie's mouth was wide open as she was groaning and she pulled my cock downward pointing at her chest as the first shot of cum fired out, shooting up hitting her neck and glancing over her shoulder onto the cubicle wall. That was followed by two more rapid fire shots of cum that hit her square in the middle of the chest splattering over her breasts. And Angie kept on stroking drawing more and more cum from cock depositing all across her breasts. She sat there with her mouth wide open continuing to squeeze my cock back and forth until all that was left was running down over her hand and onto the floor.

My breath finally started to catch up with me as I knelt down and kissed Angie. By now she was passionately kissing me back. As we broke our kiss I saw that my cum had run off her breasts and onto her gray skirt leaving large wet marks. I wasn't sure how she'd deal with that at home but I found it to be a turn on to know Angie had my cum on her rather than her husband's. I had this sense that she now belonged to me.

Angie stood up again having that slight, albeit awkward, smile and said she needed to go clean up and grabbed her bra and blouse and headed off to the ladies room. I pulled myself back together and started to think about how what happened tonight will forever change things in the office. As I sat down with those thoughts, I threw a quick email to Pete letting him know the papers were going to get to his office in two days but that we didn't need them back until the following week so there was no rush.