Sissy Boy Secretary Ch. 09

Elaine had enlisted the help of her neighbor's daughter, Tammy, to help in obtaining a big business edge for her company, now it was Tammy requesting her help. Tammy's mother was divorced from her husband after an unfortunate chain of events, some of which were Tammy's fault. It seems that Tammy's father was quite a jealous man when it came to her Mother, he never really trusted her fully, which led to the downfall of the marriage.

Here is the story as Tammy told Elaine....

When I was home on a spring break from my college studies I had a big date planned, but I left my sexy lingerie at school, forgetting to pack them. Out of curiosity more than any thing else I decided to check out what Mom had so I could borrow it. I went into Mom's bedroom to see if I could find a suitable replacement. What I found was several sets of sexy panty and bra sets, seems she liked to dress sexy, so I chose a skimpy black lace set to borrow.

The date went great and the sex even better, leaving the traces of our good time lining the panties, soaking them in a mixture of our combined juices. Without thinking, I dropped the dirty lingerie into the dirty clothes bin, right where my father found them I later learned. Instead of inquiring about them my father placed them in a bag, evidence of my Mom's misbehavior he thought. Nothing happened for the remainder of my vacation and I went back to school as I normally did.

Summer vacation was soon upon me and again I was staying at my parent's house but with one noticeable difference, the tension in the air could be cut with a knife. My father was working a lot more overtime and even when he was home, he gave Mom the cold shoulder, barely talking to her. I approached Mom about it but she reassured me it had nothing to do with me but was something she had to handle on her own so I let it go.

My curiosity got the best of me and I needed to find out what was going on, something was definitely wrong. Since neither of my parents were going to tell me, I enlisted the help of a high school friend of mine. Scott has been working with computers since I have known him so it was easy for him to wire the house for video and sound. I helped him place wireless cameras in remote sections throughout the house; parent's bedroom, living room, kitchen, and even in the bathrooms. I could monitor the output of all these devices on the computer in my bedroom. Not only was I able to see video from these devices but I was also able to direct the camera angle to see the whole room.

I monitored the video for the next week but really did not find any reason for my parent's behavior. Mom and I often ate dinner alone while my father worked overtime but the talk was always light and never personal. It was the same thing night after night, we would eat, clean up the dishes then both retreat to our bedrooms. I was surprised when on the third night I saw my Mom turning on her computer, sitting in front of it wearing only her robe. It appears she was reading pornography on a sight called Literotica.com, but I could not read what stories she was reading. My eyes popped wide open when I saw my Mom pull out a big black dildo and start to fuck herself while reading the story. I will have to find out what story it was because in a matter of minutes she was having a massive orgasm, almost falling out of the chair in the process, I guess it has been a while I surmised.

My Mom treated me to a repeat performance two more times over the next week, each ending with Mom in an orgasmic spasm. I did sneak into their bedroom and found out the stories she read involved dominating females and submissive males, you go Mom.

A few days later my Mom nervously came to ask, "Tammy would it be possible for you to find a place to sleep tonight, your father and I have to talk and we need some privacy?"

"That will be real easy Mom, what are you going to be talking about?" I inquired.

"To tell you the truth I am not sure, your father just told me that he had to talk to me about something important, he did not give me any details," she answered.

The dead silence at dinner that night was maddening; no one said a single word. I guess they were both nervous about tonight. I excused myself and retrieved an overnight bag from my room. I kissed them both good night and said I would call before I came home.

I came over here, out of the view of my parents, and waited for my opportunity to sneak back in, I did not want to miss this. I was startled when I saw my father's car leaving the driveway with only him in it. Watching I saw my parents bedroom light go on and I knew this would be my chance. Not making a sound I made my way to my bedroom unnoticed, turning on the computer as soon as I walked in.

I saw my Mom at her computer again, reading stories once more. The dildo did not appear this time so I thought that my father must be coming back and she did not want to get caught. I head my father return at the same time she did, her computer going to E Bay now.

Looking on the other camera, I was able to see that my father was not alone; accompanying him was a young woman barely older than I was. He told her to wait there until he called her then descended the stairs to their bedroom.

He found my Mom sitting nervously waiting for him at the computer desk. Putting his hands on her shoulders he leaned down to kiss and nibble her neck, knowing how horny that makes her, "I would like to try something a little different tonight to spice up our sex life, are you up to it?"

"Since we haven't had any sex in the last few months, normal sex would spice it up," Mom said sarcastically.

Ignoring the sarcasm, "So does that mean you are game, you want to try something new?"

"I am so horny I am willing to do most anything to get you to fuck me," Mom answered quickly.

"I want to tie you up and play with your hot body a while before I fuck you, it would excite me immensely," he said watching for her reaction.

"Well I guess.....what the hell?" as her hands were pulled behind the chair and handcuffed there.

"Do not worry, you will like this," he bent down to cuff each ankle to a chair leg, my Mom now bound in place. His hand rode up her leg, over her thigh and then he put two fingers in her pussy, noticing the wetness. Putting the fingers on Mom's lips,"You are wet already, you like this don't you?"

"It is different, exciting actually as you can see what it does to me," Mom noted.

"Now it is time for you to feel how I've felt over the last couple of months," my father said as he was leaving the room. Mom had no idea what he was talking about and he ignored her screams.

He returned with his lovely, very young 22 year old, secretary in tow, with lust in her eyes. Apparently, he confided in her about finding the soiled panties and asked for her help. Thinking she was going to be helping him with payback, she readily agreed to his plan. It was easy to talk his secretary into helping him since this was one of her fantasies too.

"What the hell are you talking about?" "I did not do anything!" "What in the world is this, who is she?" my Mom continued to yell at him.

"Damn that bitch is noisy, can you shut her up?" Linda, the secretary asked.

"Sure thing, I was hoping it would not come to this but I guess we have no choice," he put a gag in her mouth, securing it tightly. He returned and started passionately kissing Linda and groping her body everywhere.

The clothes flew all over as they stripped each other, both groping and grabbing each other. Linda went to her knees and took his cock in her mouth, "I can not believe anyone would not worship this cock, it is masterful," sucking it all the way in, tongue reaching out to lick his balls, (I wish I could do that I thought to myself.)

"Oh that feels so good!" "Yaa, just like that baby, keep it up!" "Damn this is better than any blow job that bitch gave me!" were some of the comments heard as she continued to give him a wet blowjob.

I watched in utter horror when I saw my father place this young harlot on their bed, licking up her thighs to her shaved pussy. He ravished her with no regards to Mom who sat only a few feet away. When I saw the way he devoured her pussy I wished it was my pussy being eaten. I noticed that my hand was now inside of my shorts, stroking my own pussy; I was getting hot watching this.

He licked/kissed his way up to take a pert nipple into his mouth, flicking it with his tongue. His other hand groped and squeezed the other tit, even twisting the nipple some invoking a scream from Linda.

"Oh my God, that feels so good," Linda yelled when my fathers cock impaled her, "Umm!"

My father pounded away at her young pussy causing Linda's moans to be almost constant now. In and out, in and out, over and over again his cock was buried in her sweet pussy. He fucked her in that position for the next fifteen minutes, what stamina he had, before he flipped her over and took her from behind. As wet as his cock was when he pulled it out told me Linda loved this, as if the moans didn't tell me that any way.

He continued his incessant pounding of this young girl from behind for another ten minutes or so, even reaching around with one hand to caress her tits. I had to admit my father had good taste; this girl had a fine ass. I was totally taken aback when my father pulled out and stepped back, allowing Linda to stand up. I noticed that his cock was still rock hard, standing at attention, ready for more and more he was going to get.

I watched Linda grab around my fathers neck to pull her self up, then she wrapped her legs around his back and mounted him, his cock going in deep. She rode him like a rodeo bull, fast and furious, up and down she bounced time and time again until I knew my father could take no more. Dad dropped Linda to her knees with his cock in her face so she could suck him to orgasm. Linda knew what he wanted so she took the cock in her wanton mouth and vigorous sucked him. I saw my fathers face squint up as he released loads of warm hot cum in her mouth which she eagerly swallowed, not missing a drop.

Linda stood up, my father put his arm around her waist and off they went to the shower, ignoring my Mom completely.

I know Mom couldn't see but could hear the two of them fucking in the shower. I switched to the bathroom cam and watched my Father fucking Linda from behind in the shower. After they were done, cleaned up and dressed my father sent Linda down stairs to wait for him.

Mom was sobbing away while my father undid her bounds, "I guess I owe you an explanation don't I?"

"You are damn right!" Mom said in between tears, "What did I do to deserve that?"

"So you would like to know what this about huh?" her father said as he walked over to the dresser. She watched as her father reached into the drawer to pull out a pair of lace panties in a plastic bag. I could see that the black lace panties were covered in cum, my cum, not hers. Results from my hot date the last time I was home. "You don't deserve it? Do these remind you of anything?" he flashed the panties in front of her eyes.

"I have not seen or worn them in the last at least three months, they came up missing one day," Mom told him. "How did you get them?"

"I found them in the dirty laundry a while back."

"Oh," it was like a light bulb going off, "Was Tammy home from college when you found them?"

"Come to think of it she was on vacation at the time."

"Why didn't you ask me then you stupid bastard? Why the hell do you always think I am cheating on you? I can not take it any more! Get the hell out of here I don't want to see you again, we are getting divorced."

"I didn't say anything because I was so mad, I was afraid I would hit you!" he pleaded.

"I don't want any excuses; you had plenty of time to talk to me before you did any thing. Now just get the hell out of my face!" my Mom roared.

My father left the house that night and it was two months later that the divorce was final, my Mom and me got the house. I never let on to Mom that I knew the real reason for what happened but I will always carry the guilt with me.

My Mom has distrusted all men since the incident, she detested them now. She has become a hermit, never going anywhere except to work or the store, spending most of her free time reading stories and pleasuring her self with the black dildo. I noticed that most of the stories involved a white female dominating a black male which gave me the idea on how to help both my Mom and you at the same time.

Now that Bill is ready for the taking I had an idea that would help you and my Mom. Let's allow my Mom to dominate Bill and have him service Sissy Boy for our hidden cameras. We can make Sissy Boy look totally feminine and let Bill think he is female until it's too late. Can you imagine the look of surprise when he finds out he's fucking a guy in the ass, even better when we show him the video. I really think I owe my Mom this and I would be grateful if you let me do this.

*

Sorry for the deviation but this was necessary to set up the next chapter. See Ch 10 for the final devastation of Bill coming soon (I hope).