Crazy Mary

Things were going so well, I was 27, I had just gotten a promotion that would provide me with a large increase in pay, and I had also just gotten married to my girlfriend of 4 years. Becca was gorgeous, she was 25, she stood 5'7, weighed in at 115 lbs. Had firm C-cup breasts, long flawless legs, a perfect face with big sexy lips and large blue eyes, with long blonde flowing hair. She was easily a 10 in any guys book, I felt very lucky to have her as I would have rated myself an 8. To top it off Becca was an absolute genius, I don't mean that in a complimentary husband sort of way, she was actually a certified genius and held a high paying job herself. With the new money coming in we were finally going to be able to afford our dream vacation house in Tahiti. We wasted no time in purchasing it and booking some vacation time. We spent 3 weeks in utter bliss, and wasted no opportunity to fuck.

Upon my return to work I learned there was a new administrative assistant working in the office for my boss. Her name was Mary, she was in her mid fifties, stood about 5 feet even, and weighed in at easily over 250 lbs. She had dark brown hair that was short and curly, and she wore a rather thick pair of glasses. Mary also had the habit of wearing clothing somewhat inappropriate for an office setting, and definitely inappropriate for a woman of her size and age. Her skirts were often too short and showed off far too much of her rather large thighs, and her blouses were often cut too low showing too much of her extremely ample and heavy breasts. Mary was perfectly nice, and most everyone in the office seemed to like her. Sometimes I felt she was often too friendly with me, and I was sure on more than one occasion that she was flirting with me. Though I must admit I was somewhat bothered by a woman I found so unattractive flirting with me, I was more bothered by the fact that I made sure she knew I was married and not interested, but this only seemed to encourage her to flirt even more with me.

I had found myself alone with her in the elevator one day and she became very forward with her flirting. Of all things, she chose to compliment my belt, which she reached out and touched, then proceeded to trace her fingers along it until her arms were wrapped around my waist, and her large breasts and stomach were pressing firmly against me. I was so shocked I wasn't sure how to respond, I tried to back away, but she held her arms firmly, and I ended up sandwiched between her and the elevator wall.

"This belt would look even better on my bedroom floor." Mary said while licking her lips.

She then winked at me, and started to pull me tighter against her, and moved her arms around my neck trying to pull my face to hers for a kiss. It was kind of embarrassing to admit, but Mary seemed to be stronger than me, and despite my resistance, she was succeeding in drawing my face closer to hers, with a very large, devious, and horny smile on her face. Thankfully the elevator suddenly slowed as we reached our floor, and Mary quickly removed herself from around me, exiting the elevator as if nothing had happened.

As I returned to my office I felt dazed, I was having trouble wrapping my head around what had just happened. I had never experienced a woman being so sexually aggressive towards me, and I was certainly upset as I never wanted anything to do with Mary, let alone to cheat on my wife. I spent the next hour in my office thinking about it. I decided that I needed to say something to my boss. Thankfully my boss was also my best friend since high school, Jeff. Ever since Mary had started flirting with me, I had avoided visiting Jeff in his office as often as I used to. Jeff's office had an enclosed front room where Mary sat, and where I would often have to wait to see Jeff, needless to say the prospect of being in a room alone with Mary was unattractive to me. However, this time it was unavoidable. As I entered into Mary's workspace I saw her sitting at the desk typing away on her computer. She looked up and gave me a very large smile.

"Did you come to see me?" Mary asked with a very sexual undertone in her voice.

"I just need to talk to Jeff." I informed Mary in a no nonsense voice.

Mary said it would just be a few minutes as he was on the phone with a client, and told me to have a seat. As I sat down Mary returned to her work and payed me no more attention, for which I was thankful. A few minutes later Mary informed me I could go in now, I stood and walked past her desk.

"Hope we get to have another elevator ride alone together soon." Mary smiled and winked.

The idea of that struck genuine fear into me, and only strengthened my resolve to say something to Jeff about her. Jeff and I were both level headed enough to keep our professional relationship apart from our friendship. If I called in sick to work, and Jeff knew I had been drinking, or just wanted to spend the day with Becca, he didn't care, as long as I didn't abuse the privilege. I took a seat across from Jeff and got right to my point. I explained to him that Mary was making me very uncomfortable, and how she was being very aggressively flirty towards me. I decided not to tell him about the elevator incident as I was slightly embarrassed by the fact that Mary had almost overpowered me. Jeff simply laughed at the situation, he said he couldn't fire Mary as she was an incredible assistant, and everyone in the office seemed to love her, with the exception of myself.

"Somehow I don't think you're gonna cheat on Becca with Mary, regardless of how aggressive she's being towards you." Jeff still found the situation amusing.

I realized that I was just going to have to weather the storm as it were, and do my best to avoid Mary. If our office wasn't on the 32nd floor I would have pledged to never take the elevator again, but that would be unavoidable. Jeff and I both knew I wasn't the type to go beyond his authority, even if we weren't friends, I would respect his decision. Plus I didn't feel comfortable begging my friend to save me from his assistant. For his part, Jeff did offer a half-hearted apology for my situation. I got up and left his office, I exited the door and closed it behind me. I was dreading turning around and seeing Mary, but as I turned I was surprised to see her desk empty. I was so relieved I had a minor celebration before quickly heading back to my office.

I walked into my office and suddenly heard the door close behind me and the lock click, my heart sank. I turned around as was unsurprised to see Mary standing there. With the door to my office closed no one in the office could see in, I also enjoyed working in the dark, so I'd had blackout blinds installed on my windows. The only significant source of light came from a lamp on my desk, and my computer screen.

"What were you talking to Jeff about, was it little old me? Were you asking him if it's okay for us to start dating each other?" Mary asked while taking a step towards me.

I was completely in shock again, I couldn't understand why Mary would make a presumption like that. I expected to be accused bad mouthing her, not asking permission to date her. I was so stunned by her statement I couldn't think of anything to say. I felt completely frozen in position, even as Mary advanced closer to me. As Mary neared I saw her smiling that same devious and horny smile, she reached out and grabbed my tie below the knot, and wrapped her other arm around me grabbing my ass and pulling me closer to her. Again I felt Mary's large stomach and breasts pressed against me.

"He wouldn't tell Becca about us would he?" Mary asked in a sultry voice.

She began to pull me by my tie towards her face, clearly looking to get the kiss she'd missed in the elevator. I felt paralysed and completely unable to react to the situation. I don't think Mary was about to stop even if I had been able to put up some resistance. Mary slowly brought her lips to mine, as they touched she continued to kiss me harder. After a few seconds Mary broke away her contact and looked at me through her glasses.

"Ohhhhh babyyyy!" Mary moaned in a squeaky voice.

She had an absolutely delighted smile on her face, I could tell she had taken my acceptance of her kiss as a sign that I was interested in her. She quickly moved her lips back to mine, she released her grasp on my tie and wrapped her arm around my neck. I felt Mary's tongue start to run along my lips as she kissed me, she was making an effort to try and push it into my mouth. She moved her other hand from my ass and placed it on my crotch and began rubbing my cock through my pants. Her touch felt like a shot of electricity through my cock, and I felt blood began to instantly rush to it as it quickly hardened. The feeling made me gasp slightly which caused my mouth to open, Mary's tongue took quick advantage of the situation as she pushed it aggressively in. I couldn't help but let out a slight moan, which Mary obviously enjoyed hearing as she pushed her tongue deeper into my mouth, and rubbed my cock harder and faster, returning a long loud moan of her own. I finally got my senses about me and pushed Mary away from me, to my surprise she relented and allowed me to, she certainly had a strong enough grip on me to stop me from doing so.

"You're right, we can't do this right now," Mary immediately remarked, "Don't worry lover, I'll set us up a date, and let you know."

Mary grabbed my cock, and shoved her tongue back into my mouth, pumping my cock several times before releasing her grasp. Mary winked at me, and turned to leave. As she closed the door behind her, I was left alone in the darkness, with her red lipstick all over my face. I went to my washroom and washed my face, I looked at myself in the mirror and felt disgusted. How could I not even put up a fight? Why did I just stand there and let her take advantage of me? I returned to my office and found that my cock was still rock hard, in fact it felt harder than it had ever been in my life. I obviously couldn't deny that what had happened had aroused me, I kept running through it in my mind. I sat at my desk going over it again and again, I became so lost in my thoughts I barely even noticed my hand stroking my still hard cock through my pants. I couldn't help it, I undid my pants and slid them down around my ankles along with my boxers, I unbuttoned my shirt, and began to stroke my cock rapidly. The whole time I couldn't stop myself from thinking about Mary kissing me, it didn't take much time before my cock erupted in one of the strongest orgasms I'd ever had, there was more cum than I'd ever produced. I quickly headed to the bathroom and cleaned myself up. It seemed like as soon as I came all sexual thoughts of Mary left my head, and I returned to my senses. I again felt very disgusted with myself, and especially with Mary. I sat back at my desk and thought about the situation with a clear mind. I decided to head home for the day, and talk to Mary tomorrow, let her know that I was not interested, and that she had to stop kissing me and flirting with me. I decided that going down the stairs wouldn't be very much of a strain, and avoided the elevator.

That night in bed I was again consumed by thoughts of what had happened with Mary, but it had been a few hours since I had cum, and to be honest it was starting to make me horny again. Becca was clearly in the mood for sex, and was touching and kissing me a lot. I felt guilty that I couldn't stop thinking about Mary, and was forced to tell Becca that I wasn't in the mood tonight, and apologized. Becca as always was very understanding, and gave me a long soft kiss.

"I love you." Becca said with her beautiful voice.

She rolled onto her side, and pulled my arm around her. Thankfully my cock wasn't hard, and I settled in close to her and fell asleep. That night my dreams were invaded by Mary. Her touching my belt, trapping me in the elevator, kissing me in my office. I woke up in the middle of the night, my cock was hard as a rock again. Becca had noticed too and awoken from her sleep. She rolled over, smiling at me, and grabbed my hard cock.

"Mmmmmmmmmmm." She moaned at me.

Without saying another word she disappeared under the covers and I felt her mouth start to work gently on my cock, she quickly started building up the pressure and pumping my cock faster. It felt amazing, I closed my eyes lost in the pleasure. Suddenly an image of Mary popped into my mind, and my cock stiffened even further.

"My god baby, I don't think I've ever felt your cock this hard!" Becca sounded thrilled.

She quickly climbed up, straddling over my waist, and slid her wet pussy down onto my cock. She immediately started grinding hard against it. Seeing her perfect body and gorgeous face was more than enough to completely remove Mary from my mind. Becca quickly climaxed, and I felt her pussy clench around my cock as she did. I followed shortly after, and again had one of the most powerful orgasms I'd ever had. Becca screamed with delight as she felt me cum. After cleaning up, we returned to bed together, and slept peacefully.

When I arrived at work the next day I saw Mary's car in the parkade, I figured she must already be here, so I got into the elevator to head up. As the elevator doors were closing I heard someone in heels approaching, figuring Mary was upstairs already, I stopped the doors from closing.

"Thank you so much!" A familiar voice said.

Mary walked into the elevator doors, and immediately wrapped her arms around my waist hugging me. The elevator doors closed, and it started making it's way upwards. Mary held her hug firmly as we passed the lobby without picking up any other passengers, it was likely this would be an elevator ride alone with Mary again. Mary released her grip, turned, and flipped a red switch that brought the elevator to a stand-still.

"Don't worry baby, there are no cameras in the elevators. Let's have some fun!" Mary returned to her place around my waist.

I decided that now was the time to set things straight and end this once and for all. I told Mary that I was a married man, she interrupted,

"(giggling) I know you are baby, I'm okay with it, I kind of like it that way."

I started again, I told her that she had to stop kissing me, and touching me, and flirting with me as it was making me uncomfortable. I told her I was not interested in her in any sexual way. Mary looked disappointed.

"Are you sure that's how you feel?" She asked.

I told her it was. Mary looked sad and turned flipping the switch allowing the elevator to begin moving again. She stood away from me, and didn't look in my direction again. She looked genuinely sad, and I did feel bad for her, but knew that I couldn't offer sympathy in this situation. We reached our floor and Mary exited, she turned and looked back at me with a pleading look in her eyes, but then turned and headed towards Jeff's office. I headed to mine, not feeling great about myself, but also feeling so relieved that this was resolved.

The day was nearing an end when I heard a knock at my door. I invited them in. I looked up to see Mary, she closed the door and locked it behind her. She smiled at me.

"Are you ready for our date my love?" Mary said as she sat on the edge of my desk beside me.

This caused her short black skirt to start to ride up her large thighs. I again felt shocked, I thought this was over, and yet here she was in my office again. I asked her what she was talking about?

"Our date remember? I said I'd set it up. I already called Becca and told her you'd be working late with Jeff tonight, so we've got all the time we need." Mary said to me like I was the crazy one.

I felt very angry that Mary had called Becca, and that she'd lied to her. I told Mary that I had made my feelings clear in the elevator. Mary simply giggled,

"That was mean, you're such a big liar! Don't tease me like that anymore my love."

I told her I wasn't teasing her, that I was being completely serious.

"Is that so? Maybe you should open your email." Mary said while smiling at me.

I opened my email and found a message from Mary, there was a video attached to it, as I opened it I saw a pair of legs sitting in a chair, the camera seemed to be under a desk. Suddenly the pants and underwear were pulled down. It was then that I noticed the chair, the pants, and the underwear, this was my office. Under a dim light from my desk lamp you could see me begin to stroke my cock. You could hear my breathing, and slight moans escaping my lips, and in not much time, cum erupting from my cock, and you could faintly hear me gasp the name Mary out loud as I was cumming. I had a bad habit of talking to myself a lot.

"Doesn't seem like you're not sexually attracted to me, that's how I knew you were just joking with me. Take a look under your desk." Mary instructed.

As I did, I saw a blue light coming from under my desk, I moved my lamp and saw a webcam mounted against the inner wall.

"I have it linked to my computer. Yesterday was the first time anything interesting had happened. (giggle) I guess I had quite the effect on you, maybe I should have just stayed." Mary said smiling and winking.

I was again in shock and unsure of what to say. I noticed the light coming in from under the door, click off, the office had emptied out.

"Mmmmmm, perfect. Looks like we're all alone here now baby." Mary licked her lips.

Mary slid off my desk and turned around, she then sank her very large ass down into my lap. I was immediately pinned down under her weight. She started to grind back and forth on my crotch, and betraying me again, my cock began to respond. Mary could clearly feel my cock begin to press against her ass and she moaned,

"There we go baby, let's finally do what we've both been wanting for so long!" Mary's voice was seductive.

Mary stood from my lap and turned around, she quickly returned to my lap with her pussy planted firmly on my crotch, and her stomach and breasts pressed into me. I was pinned yet again. Mary grabbed the hair on the back of my head, and shoved her tongue into my mouth. She moaned repeatedly and loudly. I tried to push her away and ended up with two hand-fulls of breasts, which in turn caused her to squeal in delight, she reached down and unfastened my belt with surprising efficiency. It took her no time to have my zipper down, she reached into my underwear and I felt her hand grasp the shaft of my cock. She squeezed it tightly and began pumping it very fast, it was again incredibly hard, and felt so sensitive to her every touch. Mary was clearly excited by my aroused state, with out removing her tongue from my mouth, she pulled her underwear to the side, and slowly lowered her pussy onto my cock. As I felt the head slide into her, Mary began a long steady moan into my mouth. Her pussy was surprisingly tight, and the sensation of it lowering onto my cock caused me to let out a long loud moan. I felt Mary's lips curl up into a smile as she kept her tongue firmly in my mouth, she slightly lifted her pussy, then slowly lowered it a little more. This again caused me to moan loudly. Mary giggled and kept repeating the process until finally her pussy settled with every last bit of my cock buried inside her. Mary and I simultaneously let out long moans of pleasure.

"Mmmmmmmm, finally baby. I know you've been dreaming of this, so have I, we were meant to be together." Mary returned her tongue to my mouth.

She began slowly grinding on my cock, every shift of her weight sent a wave of pleasure through my cock, I couldn't stop from moaning loudly. Mary removed her tongue from my mouth and smiled at me as she continued to grind away on my cock, slowly increasing her pace, and force.

"Ohhhhhhhhhh Mary..... Maryyyy." I gasped.

"I love you baby.......... Mmmmmmmm..... I know you love me too!" Mary gently kissed my lips again.