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My Boss Didn’t Know How to Ask

Category: Anal Sex
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Working for a female boss is not something I really had a problem with in principle, but working for my female boss was a definite problem. She was definitely the type to make sure everyone knew she was in power almost in a way to counteract the “weaker sex” stereotype. She was a 40-year old divorcee which really wasn’t a surprise as there was no question that she was an attractive woman, but at the same time I can’t imagine anyone living with her personality.

Something about the combination of blazer and skirt outfits attempted to make her come across more feminine but the looks she would give while barking out orders to me and the other staff made any attempt of softening her look into more of a joke.

I can’t deny that she did have great legs, and I can remember on more than one occasion thinking how sexy it would be to have those legs wrapped around me while I gave her the kind of sex that I think she exactly deserved. It wasn’t just me that felt like the wicked witch from the west was our boss. Every one of my 12 co-workers felt the same way, especially the women. How our boss could ever be considered a mom to her child was a common question as it didn’t seem there was any love in that woman for anyone.

When I was first hired, she seemed like a legitimately nice person. I suppose as her relationship at home with her husband deteriorated, so did her behavior at work. She didn’t often ask for things to be done, she told us of her needs. “Jim, I NEED you to get me that report earlier than I told you yesterday” was a common ‘request’ of hers, only substitute my name for anyone’s name and ‘report’ for anything from data to coffee to lunch. I was not hired as her personal assistant but increasingly it was me or Pamela that were being treated as such. Lunch or coffee was one thing when either one of us were already going to get it, but if I ate at 12:30 and she needed lunch at 1:30 it was going to be a problem.

It was more than a problem of course when she would then complain that I didn’t finish my work on time – work that she demanded done sooner than she had needed it done in the first place. Pamela joked that we should start spitting in her coffee or her food but I really thought that was gross and I told her that I was just going to start looking for a new job instead of lowering the standard of my behavior.

One day my boss called me into her office. Her sandy blond hair was up and she had her usual glasses and lipstick look on her face and her favorite plum blazer and skirt on. I swear she wore that thing 2-3 times a week but maybe the days were just blending together. As usual I could tell she needed something from me. She told me that we had a very important client staying in town and that I had to deliver a manilla envelope to them right to their hotel room. She emphasized that I was not to open the envelope nor answer any questions about it but to just give it to the client and when they had it I was to leave them alone. I took the envelope from her and was surprised how light it was despite how it seemed to have something somewhat bulky in the bottom.

She said she needed it delivered on my way home tonight and that I could leave a little early to be sure to get to the client by 5:30pm. It was a Friday and I had plan to meet a few of my co-workers for drinks at 5:00 or so and of course my boss was ruining it for me. I took the envelope and told her I’d take care of it. On the top of the envelope was the name of a nearby hotel and a room number. I’d never been asked to do something like this and it seemed so strange.

The day went by relatively quickly and when my boss told us just as she was leaving that she wouldn’t be back until Monday, I looked at the clock and realized it was already after 4:30. That was great news for everyone else as they were heading out for drinks shortly but I of course was expected to be the messenger boy for my boss as my final task for the week. With the hotel about a 10-minute drive away, I headed out the door about quarter after clutching the envelope. I got in my car and was surprised how calm traffic was. I figured I could drop it off to the guy at the hotel and get to enjoy round 2 or so with my co-workers without problems. I looked over at the package on the seat and noticed that it was lying face down and had one of those red string tabs holding it shut. I could open the envelope and check out what was inside and the client nor my boss would ever have to know. I undid the string and opened the flap. Inside was a contract not unlike the typical ones we make every day.

I pulled it out to see that it was going to a client we did occasional business with…a pretty boring envelope after all. Why did she need it dropped off on a Friday afternoon when it was done in the morning though? Suddenly I realized that there was more inside the envelope. I reached down and felt something somewhat foreign and soft and when I pulled it out I found it was women’s underwear, specifically a very sexy black lace thong! What the hell was going on here? I looked over the underwear and noticed that they were obviously worn and realized that my boss was doing something on the side with this client…and I was in the middle of it! I was pretty grossed out thinking about some ugly fat man fucking my boss, but couldn’t help but be turned on having her panties in my hand, almost empowered slightly by it.

I placed the panties back in the envelope and grabbed the contract and slid it in as well. Then I noticed that a yellow sticky note had fallen off the contract. I picked it up and read what was obviously the hand writing of my boss. “Hope you find what is in the envelope satisfactory. Looking forward to meeting you at 6:00pm…XXX Sandra”. Holy smokes, she was doing exactly what I thought. Who sends her panties in with a contract, who signs a note “XXX”, and more importantly why was I the lucky moron who had to drop this off for her? I closed up the envelope and headed into the hotel. It was a nice hotel but I really could have cared less.

I was pretty put off that I was being used as a messenger boy delivery sex notes to my boss’ lover. In the elevator I thought about some guy giving it to my boss. It actually was a bit of a turn-on thinking about her getting what she deserved and I half contemplated waiting around until 6pm just to see the look on her face when I showed up late with her envelope. I really wanted a drink and to share this with my co-workers though so I decided I would instead keep my job and tell everyone that our boss bangs at least one of our clients.

I got to the door of the room, and knocked despite that the deadbolt was out keeping the door ajar. I was shocked when I heard a woman’s voice tell me to come in and shut the door. The voice was coming from the bathroom I figured. My boss was fucking a woman?? Oh this was getting too good. I walked in the room and closed the door behind me, telling the voice that I had the envelope that Sandra told me to deliver. The voice told me to put it on the bed and thanked me. Wow, somebody thanked me for this whole stupid thing, but I wasn’t about to let that stop me from telling every single soul at my workplace that my boss sent her panties to some chick that she was planning to meet at this exact spot for sex. Oh to be a fly on the wall when that all went down.

Once I was thanked I dropped the envelope onto the bed, noticed that the TV was on set to CNN and started to make my way out of the room. I had just got to the door and had almost opened it when the voice spoke a third time. It was right behind me and kind of startled me. The voice asked where I was going. I turned and I swear my jaw dropped, and I mean literally dropped. There right behind me was a pair of sexy legs in black thigh highs. The thigh highs had red garters on that were attached to a black and red garter belt. There were no panties covering the bald pussy right below the garter belt. Above the smooth sexy stomach were two firm breasts barely contained in a see-through bra, a very sexy neck, and my boss’ head at the top. What was going on here? I think my boss understood my confusion and that made her smile. She told me to keep the door closed and then walked up right to me, right into my personal space. She put her mouth right beside my ear and asked if I liked what I saw as her hand squeezed the hardening bulge in my pants.

Was I just invited to join my boss and her lover in a threesome? Were they expecting me to join in, possibly playing with both? I was really not comfortable with that idea at all, despite how my stiffening erection was betraying how sexy my boss looked in her lingerie. She leaned in and kissed my neck and then whispered in my ear that I had been doing a really great job for her lately and while she didn’t have money to give me a bonus that she thought she could give something else that I would really enjoy. Her hand had not left my crotch yet but I still couldn’t believe she was being serious. She had some sick plan in store for me, I could feel it. She started to unbutton my shirt and slid her hands under under my t-shirt.

She didn’t say any words but seemed to be enjoying feeling my chest with her bare hands. I was honestly in a state of shock, so while maybe it came as no surprise that she reached down and unzipped my pants in order to start to feel my cock through my boxers my brain was having a hard time keeping up with what was going on. Finally I was able to form words just as she pulled out my cock from my boxers and into her bare hand. I asked if we were expecting anyone else and she shot a quick glance up at me and with a wicked smile she shook her head. She squatted down right in front of me and took my cock into her wet mouth. My boss was giving me a blowjob. In fact, my boss was giving me one of the best blowjobs of my life. Her mouth was relaxed and very wet and my cock went to full erection seconds from the moment she took me inside her mouth.

She sucked me like that, with my back up against the hotel room door for maybe a couple of minutes before she said we should go to the bed so we could be more comfortable. She helped me completely out of my clothes and I lay flat on the bed. She straddled my feet with her body and resumed where she had left off at the door. Where did she learn to suck a cock like that? Her head bobbed up and down and the pleasure she sent through me made me want to close my eyes but I couldn’t help but watch my boss sucking my cock. She moaned while she did it and that only made the whole thing hotter for me. She looked up at me at one point and started to flick her tongue over the back of the head of my cock. Little shots of bliss shot through my body.

Next she licked up the shaft over and over, making me feel like a hung stud getting worshiped by her. My cock had never felt or looked bigger in my life. By the time she lengthened the strokes of her tongue I was half expecting it. I had not really ever had my balls licked before but she didn’t seem to object in any way. She even licked my ass a little and while that was not something I ever thought I’d want, it felt really hot. After the blowjob got me as excited sexually as I could remember being, she asked if I was ok if we licked each other for a while. She pointed out that she was waxed the day before and smooth as a baby. I was a little put off by her description and really wouldn’t have minded that she had hair down there up until the moment when she straddled my face and I got my first proper look at my boss’ completely smooth pussy. It was quite pink and it was apparent that she was quite turned on by what had been happening.

Moments later and we were locked in 69 together. She had a very delicious scent and taste and the experience of licking my first hairless pussy combined with the thought that it belonged to my boss and she was busily slurping on my cock just made the whole thing better. Suddenly I was aware that things were starting to feel “too good” and told my boss that I was going to cum. She immediately stopped sucking me and told me that she didn’t want me to cum yet and disengaged from our 69 session. I would have been perfectly happy to just lick that sweet pussy some more, but apparently she had other plans for me.

Straight to the point as always she told me that she had just bought a strap-on and wanted to use it on me. She really didn’t have a way with men or with words did she! That would be like me taking a girl on the first date, and telling her while I invited her up for coffee that I loved her ass and wanted to literally fuck it. It’s sexy to think things like that but there is a time and a place…but what kind of a guy did she think I was? I server her all day long and then get bent over and fucked at night? I don’t think so! Then she pulled out her trump card. She rolled onto her side in a sort of single-person spoon position and lifted up her top ass cheek.

She asked me if I wanted to be the first to fuck her ass. She told me that her whole relationship with her ex-husband and with many guys before they had asked for anal sex with her and she never would allow it. Finally with her husband she said she would let him fuck her ass if he let her fuck his first. He told her that wasn’t going to happen so the backdoor was shut and locked for him. Now, though, she thought she would really like to explore with somebody new, somebody that she thought was extremely sexy and somebody that she wanted to explore with.

I was honored but quite scared. I told her I wasn’t sure about having anything in my ass, despite how insanely hot her idea was. She put on a sort of frown and then told me to stay where I was. She pushed up on my legs and started licking my balls again. I really loved the idea of my boss licking and sucking on them, she was really good at it and it was also so naughty that it was her of all people doing it to me. Then she licked my ass, and not a quick little flick like before either. She licked right around it, and then across it and then finally she started to slide her tongue into it. I have to admit, I’d never had my ass played with before or touched it myself but it was feeling pretty sexy. She paused for a moment and asked if that felt ok. I told her it did so she kept on going, only now she was really sliding her tongue into me.

It felt quite strange to be invaded this way but I decided finally that it really did feel pretty sexy and I was going to be fucking the one woman in the world that was my secret fantasy. I honestly would have been happy to go fully into her pussy, but the fact that she offered her virgin ass for me to explore was the kicker. By the time she got out some lube and started to rub around and slide a finger into my ass while she sucked my cock I figured this really wasn’t so bad at all. It’s not as if anyone had to know what I was about to let be done to me. My boss slid in a second finger and while it stretched me quite a bit more it didn’t feel bad. Her oral skills more than made up for any sort of uncomfortable feelings I might be having about liking what was happening in the back.

After I was quite used to having her inside of me, I told her I was ready for more. She gave me a delicious smile, which scared me slightly as I was not used to seeing this woman smile so much, so genuinely. She pulled out the sex toy from her purse of all things and I was impressed that it seemed to have something at each end. She pushed it through the harness she had and then slid the one end inside of her pussy while she pulled the straps tight around her waist. The head of the cock she was about to be offering me bobbed as she moved and it was insane to think I was actually letting this happen.

I asked how she wanted to do it and she suggested that she get on the bed and have me lower onto it. It wasn’t at all what I thought she was going to say but I decided this way I could control how things were going to happen and it seemed like a pretty good idea. My boss took off her bra and told me I could squeeze her breasts if I wanted to. I straddled her and started to rub her fantastic breasts. She was a lot bigger than I would have guessed and the pink around her nipples looked delicious as did the comparatively tiny pointed shapes of her erect nipples themselves. While I played with her breasts she took one in her own hand as if to show me how to play with it the right way for her. Instead though, she raised her head off the bed opened her mouth and began to lick at her own nipple.

I had never seen this in my life and started to guide my ass down onto her cock. I felt my ass was well lubed but I still grabbed the bottle that was beside us and coated the cock with more. This wasn’t going to be uncomfortable for a lack of lube at least. I slid down and down onto her and on one of those pushes the head just popped right into my ass. It literally took my breath away for an instant but when I regained control I started to slide it up and down inside my ass. It felt so amazing I was shocked. I could feel my cock start to harden despite the fact that nothing was touching it at all. Soon I was well used to the shape and size of the cock inside of me and began to ride her. Of course, since the cock was also inside of her, this had a double pleasure effect. My boss began to really moan while I slammed my body down into hers, driving the end that was in her pussy deeper into her.

I was amazed by how sexy it felt and while I wasn’t about to shout it from the rooftops for the masses to hear I honestly couldn’t believe it could feel that good. Finally after maybe 5 minutes of this she told me that she was starting to cum and asked if I could bend over for her. I would have done anything at that moment to keep the pleasure going. I picked up off of her body and bent over near the head of the bed. I felt her get behind me and guide the cock into my now well-lubed and open ass. She fucked me almost as hard as I fully intended to fuck her and maybe within 2 minutes she was grunting out the first orgasm of our encounter. She slowly pulled out of my ass and collapsed beside me. She took off the harness and slid the dildo out of her pussy. Her pussy glistened showcasing how wet she’d become.

She told me she was still going to let me fuck her but that we were going to need to wait a couple of minutes. It was a bit of a letdown as my cock was ready to get the show going again. I looked at her sexy body, the thigh highs and garters still making the most of her legs and the bald smooth pussy and large round breasts. This woman was one of the most annoying and irritating people in the world and now I discovered also probably one of the sexiest. I leaned in and began to suck at her large breasts. They were by far the biggest I’d ever sucked and I could tell she enjoyed feeling my hunger on her. After a while of it she asked if I wanted to try sliding between them. I didn’t actually understand what she wanted, partially because I was transfixed on loving her breasts with my mouth and also because nobody had ever offered her breasts to my penis before.

I looked up and I guess my confused look told her I needed some guidance for some strange reason. She pulled away and rolled onto her back and told me to straddle her stomach. As I did I started to catch on, especially when she took hold of each breast and pushed them closer together. I took my cock in my hand and lowered into the cleft formed between her breasts and she wrapped them around me as much as she could. I guess I had wondered before how this might feel and now I knew…it is definitely not a pussy you are fucking but still so sexy. I watched her face while I slid my cock in and out of the small space left for it to fill. She was legitimately loving this, and I decided so was I. By the time she told me she was ready for me down below I was almost ready to explode.

She told me she wanted me to fuck her pussy for a bit before trying anything else. She told me that she wanted to stay my boss and not my baby’s mother and tossed a condom to me. I slid it on and then slid inside of her. Her pussy was quite wet I could tell even with the condom on. I slid in easily but I tried to take my time so that I didn’t get to the finish line before I had really started to enjoy the race. I realized quite quickly that she loved it when I was all of the way inside, so I stayed up inside quite deeply and then pushed a little more over and over. She moaned and groaned and writhed and it was perfect for me because it felt really great but there was not nearly enough friction to drive me over the edge.

After a good amount of this she told me it was time, and to pull out, lube up and to fuck her ass. Just hearing her say those words made me shudder in excitement. I applied a lot of lube to myself and watched as she rubbed some into herself. I told her to try getting on top just like how I had done because it was really easy to control. She agreed and we flipped around so that I was below her. She lowered down and down and I watched her close her eyes at the moment I felt my cock pressing into her. She pulsed with very small strokes and realized somewhat belatedly that she was working the head of my cock inside. To me it didn’t feel like I was getting anyway but suddenly I felt the pressure drop off significantly on the head of my cock and I realized that she had got me inside.

She stayed like that with very feint motions and then she started to pick up the pace. She was a very loud lover anyway but the sounds she made while I was stretching her previously untouched ass were almost alarming. Her tone was much deeper, more guttural and so sexy. After a few moments she got up off of me and walked over to the couch. Bending over it, exposing those sexy long legs in those hot thigh highs and the ass that belonged to a 20-year old and not a 40-year old, she invited me to come and fuck her.

I practically jumped off the bed and got in behind her. I took a grip of my cock and started to guide it towards her opening in the rear. She reached back and spread herself open giving me a good view of where to go. When she felt my cock getting close she surprised me by pulling off the condom and telling me I wasn’t going to be making babies were I was going. I couldn’t believe what I was about to do, the dragon I was about to slay, and had she not the words she did, I might not have believed she really wanted what I was planning on giving her. She told me she needed me to fuck her ass as hard and as deep as I wanted, and let me tell you by the time I was inside and we were both comfortable I did exactly that. I fucked my boss in her ass as hard as I had ever gone in any person.

It was my third time having anal sex in my life but I’d never been given permission to do what I did. The sound of my abdomen slapping into her firm curvy ass shocked me, but the grunts and moans that I made my boss utter blew me away. I grabbed a couch pillow and covered her mouth with it while my cock used every one of its inches to completely stretch and fill her. By the time I knew I was about to cum I barely was able to mutter the words and hear her tell me to just cum in her ass before my balls released their thick white fluid and I flooded the inside of my boss’ ass. I pushed deeply into her with slowing strokes and made sure every drop was deposited into her before pulling back out. She turned and looked at me with a sexy almost confused gaze. I had literally just fucked my boss’ brains out and we both got off on it.

She kissed me deeply after that, her tongue was wild and aggressive and I loved it. By the time we were done kissing she told me she had to go drop her daughter off at her ex-husband’s house from daycare but that I had just given her the best sex of her life. Of course the feeling was completely mutual and I told her that she was by far the sexiest woman I’d ever been with. I started to get my clothes on while she started to pick up the room. She pulled the panties out of the envelope and slid them up her body thanking me for returning them to her. Then she told me that she had the room booked for the full weekend and told me to give her a call if I wanted to come back for a little more fun. I did, and decided that I wouldn’t be telling my co-workers about the panties in the envelope after all. I noticed my boss was a lot nicer to me after that day for some reason…

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