My First Encounter With Maryann

I first met Maryann at work. We knew and liked each other, and over a couple of years became very friendly.

I was always intrigued by her, as it was obvious that she was a very assertive, domineering, and confidant woman. I had only met her husband a couple of times, but it was very apparent who wore the pants in that relationship. For me being a closet submissive to women, I was particularly fascinated by her.

I would often playfully and somewhat jokingly flirt with her, and ask her when she was ready to run away with me. She would usually say that I wouldn't be able handle being her boy, and that I should just stick to fantasizing about her while I abuse myself.

One time she left some paperwork on my desk for me to handle for her, but I didn't know what needed to be done with it. When she came to me later in the day and found the paperwork unfinished, she scolded me in such a way that it was sort of playful, but at the same time aggressive and a bit belittling. I told her I was sorry and that I would finish it up for her immediately.

Then I jokingly said that she should probably spank me to make sure that I learned my lesson. She then sat on my desk and told me that I always say things like that, but that she seriously doubted if I was man enough to take a spanking from her. The tone in her voice was not playful; it was very serious and somewhat stern. She had a wicked smirk on her face as she turned and walked away. The way she had spoken to me made my cock painfully erect. In fact, my cock was actually throbbing so much that I thought I might ejaculate in my pants without even touching myself.

A couple of weeks later she had a deck party at her house and asked me to come over. I was happy to be invited because I knew that her husband would be there, and I always loved to watch the way she bossed him around. I found her obvious dominance over him to be very arousing to witness.

I was also curious to see if another guy that Maryann was friendly with would be at the party. His name was Gary, and he and Maryann would often meet up and go to lunch together. Rumors abound that they were having an affair, and it was actually difficult to imagine that they were not doing something naughty together.

Gary was indeed at the party, and at one point Maryann had both Gary and her husband come in the house to help her with something. They disappeared for about twenty minutes, and when they came back the men were hauling a fresh cooler of beer.

The appearance was that she needed the men to help get some more beer, but in actuality, that was just a cover. I later found out that Maryann's husband was a cuckold and that she brought the two men to her bedroom so that Gary could fuck her while her husband watched and everyone out on the deck was having a good time. This is something that I found out directly from Maryann later that evening.

As the party began to wind down and people started leaving, Maryann asked me if I would stay and help her clean up. She also told me that she wanted to show me something. I happily agreed and I asked her what she wanted to show me. She playfully said that I would have to be a patient little boy and wait until later. I said ok and was very intrigued, but I really didn't think it would be anything of significance.

By the end of the evening everyone had left except Maryann, her cousin Jennifer, her husband, and me.

The four of us went to the living room, presumably to sit and chat, but then Jennifer said to Maryann something like, "Shit, I left it in the car". Maryann rolled her eyes then said to me and her husband, "Boys, Jennifer and I need to speak privately. Go stand outside on the deck until we are ready for you". Her husband immediately said yes ma'am, and I followed by saying it as well, but with a little bit of a smile on my face. Maryann did not return my little smile and just leered at me pointed her finger towards the deck.

Her husband and I stood outside on the deck together and shared some uncomfortable chat and a lot of awkward silence; actually, just about ten minutes of silence. Then the lights on the deck flickered off and on, and her husband said that meant it was ok for us to go back inside. The way he said that, I had a bit of a moment of clarity and immediately thought that I was involved in something quite a bit out of the ordinary.

Once back in the house, Jennifer got up and started walking toward the stairs. As she did she said, "Come on, Andy (Maryann's husband's name) and gently slapped her thigh a couple of times when she said it – pretty much the way someone would call a dog. Andy immediately followed Jennifer up the stairs without saying a word. Now I really knew something odd was brewing.

Maryann walked me over to the sofa chair in the living room and simply pointed at the chair and said, "Sit, boy". I obeyed without a word; somewhat due to the fact that I was a little stunned and extremely aroused.

Maryann explained to me that her husband and she had a legitimate D/s relationship, and that he was indeed her little bitch. She also told me that he was a cuckold, and explained that earlier in the day when she called Gary and Andy in to help her with something, that they actually went to the bedroom and Gary fucked her while her husband watched.

Then she explained to me that earlier in the day Andy accidentally stepped on Jennifer's new pointy toed spike heels that had only been worn once. Although he did not scuff the shoes, he did need to be punished for his clumsiness.

Maryann told me that she was going to give him a hard spanking while Jennifer watched. She also thought that it would be good to let me watch, because it would add to her husband's embarrassment, and that I would finally get to see what a spanking from her was like.

She stood up and said, "Now, let's go have some fun upstairs". As she began to turn she did the same thing Jennifer did earlier, and slapped her thigh a couple of times and said "Come on boy". I silently followed her up the stairs. Part of me was very excited and part of me was nervous as all hell.

Once in the bedroom, Maryann had me sit on a chair right beside the bed. Jennifer then walked Andy over to the bed. He was between where I was seated and the bed and he was facing the bed.

Jennifer then leaned towards Andy and said in a very sexy voice, "Show time. Drop those pants". Andy obeyed and dropped his pants all the way down to his ankles. He was bare-assed, and Maryann told him to lay face down on the bed. Maryann looked at me while she folded a leather belt, and told me that this is what to expect when receiving discipline from her.

She was not gentle or playful when she began to beat his ass; she delivered a serious ass-whipping. Her and Jennifer were laughing and having a good time though.

When she was finished beating him, he was told to get up, and with his pants still down around his ankles, he was made to walk over to the other side of the room and stand in the corner like a bad little boy. Jennifer was laughing like a little schoolgirl and walked out of the room saying that she had to go pee.

Maryann sat on the edge of the bed looked at me and asked me if I still thought that I was man enough to take a spanking from her. She said, "If you think you can handle it, I would gladly consider involving you in some of my future activities". I was very intimidated, but I told her that I thought that what she just dished out was more than just a spanking. Then I told her that I could still handle it.

She said with laughter in her voice, "That's great... Stand up". I stood up and she snapped her finger and pointed to the spot on the floor in front of the bed where her husband was standing before. I walked over to the spot and she told me to drop my pants and underwear and assume the position on the bed. I did so and waited for her to begin while she paced behind me with her high heels clicking on the floor.

Then she yelled to Jennifer and said, "Jennifer, get your ass back in here. The little boy thinks he's man enough to take it". Jennifer's heels clicked loudly on the hardwood floor as she scooted back to the bedroom. When she came back in the bedroom she said, "Wow! I can't believe he agreed. I really thought he was way too much of a pussy to take a good hard one". There was a brief pause between the ladies then they both started laughing and Maryann said, "Well, we haven't gotten quite that far yet". This was followed by more laughter and Jennifer saying, "He actually does look like a closet faggot. I bet he is no stranger to having things in his ass". I was red faced with humiliation and extremely aroused at the same time.

Then I heard Maryann say, "On with the show". With that I received the first stinging blow to my ass with the belt. The pain was more than what I imagined it would be. Maryann was not fucking around; she beat my ass. All the while her and Jennifer laughed and talked, belittling me, and questioning my manhood. Jennifer kept saying that she really thought that I was a faggot. To which Maryann said, "That's ok, faggot cock suckers make great pets".

When the beating ended, I found out what it was that Jennifer said she left in the car earlier. It was a digital video recorder. Jennifer had recorded the entire beating. I was humiliated and very frightened as to what the women would do with the recording.

Maryann told me that I did very well and that she would be using me again real soon. She then told me to put on my pants and told me to scoot on home now, giving me one last slap on my sore ass as she said it.

Jennifer was already looking at playback of the video in the view finder and giggling with genuine amusement that was bordering on glee. She said, "Bye faggot. Maybe next time we can get you something in that fairy ass of yours. Oh, and when you get home and spank that tiny little faggot cock of yours tonight, make sure that you eat your cum and think of me while your doing it".

I was too overwhelmed with shame and humiliation to say anything back. I just left to the sounds of the two women laughing at me.

When I got home, I did spank off to the events of the evening, and I did lick up my sperm while thinking of Jennifer.