Blackmailing My Mom's Friend

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On a last minute spur of the moment I decided to head home for the weekend. College is great but I just needed to get away and I knew my parents were at an annual party and would be home late. With these late night events my mom has her best friend Linda baby-sit. My parents divorced a couple of years ago and my mom remarried, hence that is why there is a new baby in our family. My mom is kind of a control freak and no one else is worthy enough to watch her little baby girl.

Linda just turned forty and has been married to Frank for twenty years. She is what all my friends call a hot milf. She is so hot but has no clue and kind of acts like a prude but deep down I've always felt that there was a bad girl in her. She's five six and supports a sexy 36b breasts, long tone legs, and shoulder length blond hair. Linda and frank live three blocks away which makes having her baby sit very convenient.

I didn't tell my parents that I was coming home for the weekend as I didn't want to get stuck babysitting. Parked my car in the street and made my way into the house, only to find no one around. Well it was kind of late so I'm sure Linda had put my sister to bed but where was Linda hiding? Then I found her in my parents room, worse was that she was trying on my mothers clothes!

Linda jumped when she noticed me watching her, "You can't tell your mom, she will freak out and kill me!"

"I know she will as she's not one to share." I walked over to her, closer. Linda looked very uncomfortable as she knew she was busted. "You are so busted!"

Her face turned beat red from the fear, "What do you want? I'll do anything."

"Anything?" I had her, Linda broke! I've always thought that she was sexy and now I'm going to see all of her.

"Anything within reason."

I knew where my mom kept her sexy clothes and started to look for the perfect slut outfit. Linda was mostly a conservative dresser but tonight I'll be bringing out the slut in her. "Here, I want to see you in this for starters." I tossed her a black sheer teddy.

Her hands went on her hips in protest, "What? I can't wear this!"

"Sure you can, who will see you?"

"Well you for starters. You're my best friend son!"

"Shame, wonder what Sue will think of you in her dress." I showed her the picture that I had taken on my cell phone.

"Bastard! She walked over to the bathroom.

Her face turned flush but I pushed, "Linda, I think we're past that stage and its time to start a new type relationship. So, why don't you change here. That way, I can see how sexy you are."

I think she was excited by this, being told what to do. Frank was a nice man and I'm sure he never demanded anything or did he order her around.

She held up the sheer teddy, "You expect me to wear this?"

"Yes, I do."

Playfully this time, "Perv!"

"Excuse me? You're the one who is wearing my mother's clothes. You're the one in trouble. All I'm doing is helping you try on a few things." I walked up next to her, "I'm going to dress you like my dream woman, a very sexy woman, and bring out the hot milf in you."

She took a deep breath, and I could see her nipples were rock hard. Yes, she wanted this just as much as I did.

"Why I never." Her fake protest duly noted.

I took a couple of steps away from her, "True, but tonight you will."

Linda started to undress and asked me to help with the zipper. Once she was unzipped I walked over and sat down on my parent's bed. Slowly she pealed out of my mothers dress. Nice, she did have a hidden wild side as she was wearing a thong and sheer bra. That was the first time I've seen most all of Linda. She looked down as she started to enjoy the naughty feeling, and she removed her bra letting it fall to the floor.

Why on earth would you ever want to see me in this?" She held up the teddy, "I'm an old lady and you can have any young hot thing you want."

"Please, no your not! Look." I held her hand and walked over to the full length mirror that my mother used. "See, you're a beautiful woman that knows how to carry herself. Granted, you dress on the conservative side but tonight you're going to be one hot lady!"

I noticed the wet spot in the front of her panties, "The girls that I've been with are just that, girls. You are a beautiful woman." I knelt down and slowly pulled her panties off. Oh how I wanted to taste her but for now I enjoy enjoyed her sexy scent.

I can't believe that my Linda was standing in front of me, nude! I've been having fantasies about her since the age of ten and now I can see all of her. Linda didn't look uncomfortable; her eyes would look at me and then her own body. I think she felt sexy and wanted to experience what I had in store for her.

"What do you want with me?"

I reached out and cupped her breasts, enjoyed her teasing her sexy nipples. After a few seconds, I pulled away and grabbed the teddy. "This for starters." I moved back to the bed.

Linda didn't hesitate and put on the teddy. Her hairy bush was clearly visible through the sheer teddy; her nipples poked though the sheer nylon material. Next time I will have to trim or shave her. I never really understood why my mom had some very sexy almost slutty clothes but tonight I was happy she did as Linda was going to model them for me. I went to my mom's lingerie drawer and pulled out some stocks, told Linda to take a seat on the bed and rolled the hose up. She lifted up her left leg first, as I placed her toe in the hose, and slowly rolled the hose up her tone thighs. That pushed me over the edge and lost control, no longer was I able to hide my appreciation. Next came her right foot, and when she placed her stocking foot down, well she teased my hard cock a little.

I walked over to the closet and pulled out a sexy leather mini skirt. With out saying a word she came to me. Again, I helped Linda in the mini skirt. Her pussy no longer visible but her nipples were proudly showing. She admired her self in the mirror and I told her how sexy she looked. My mother had these perfect cfm heels that I wanted her in, I grabbed them and helped Linda into the heels.

"Wow, you look amazing."

Linda stood there and something changed in her, "I feel amazing! I've never dressed like this before."

To complete her outfit, I grabbed a black leather jacket to match the mini skirt. Linda started to walk around the bedroom, and I swear she started to walk differently. She was confident and oozed sex and was proud of herself. She held her hand out for me and I pulled her close, we started to dance slowly and very close as I wanted her to feel my approval.

Oh how I wanted to take her out in public and show her off! Something told me that she was not ready for that, just yet. As she admired herself, I quietly took some pictures of her which she didn't seem to notice, and slowly opened the blinds so that anyone in our back yard could see the hot cougar that I was about to enjoy. My parent's house backs up to a state park but still the idea was exciting, that anyone could watch me seduce her and enjoy her charms.

The jacket was light and more for show then warmth. She had the jacket zipped up. I reached for the zipper and started to pull it down, Linda gasped, "Don't you think that this makes me a slut?"

No, I don't." Her nylon breasts became visible again. I reached in and cupped her left beasts, "You have amazing firm and sexy breasts, why hide them?"

"You think?"

Reaching around my hand found its way up under her skirt. She was wet! Linda didn't stop me and I think she even opened her legs a little allowing me access. First I slipped a finger in her, then a second. Linda was amazingly tight!

I turned her around and kissed her hard on the lips, slowly the passion built as we held each other. Her hands went up and down my back and a couple of times she even grabbed my ass. I guess after twenty years of being in bed with the same man your ready for some new meat.

Linda knew that I was going to do her and that she will have her second lover. I removed her jacket and let my hands roam over her body, more importantly let her become comfortable being exposed. Which I think she loved!

We danced for twenty minutes and then it turned into bumping and grinding. Linda kept on pressing her pussy against my thigh as she couldn't get enough pressure against her throbbing clit.

I grabbed her, lead her over to the window and pressed her against the window. With a quick flick of my hands my pants and boxers were on the floor. Then kissed her neck, and worked my way down her back so that I could unzip that mini skirt. Once the skirt hit the floor she stepped out of it.

Her scent was intoxicating and wanted to taste her, I slipped a finger into her. Then a second finger of mine entered her wet pussy. Linda moaned and pushed herself down, making my fingers dive deeper into her. She wanted it and I was more than willing to give it to her. I pulled my fingers out and licked them clean, now I wanted to fill her with something else.

When I came up my cock rested between her legs and I swear that I could feel my cock becoming wet from her. The flood gates were opened as she coated my cock. Linda reached down and guided me cock into her. Slowly she devoured the tip of my cock, moaning and groaning trying to get more of my cock in her. The angle just wasn't right to allow me deep penetration. I reached around and grabbed her, lifted her up and settled her down on my cock! Now, she had everything that I had to offer stuffed in her pussy. I carried her over to the bed, with each step my cock pushed in and out of her giving her pleasure.

"Oh that's it, make me your slut!"

I've never heard her talk dirty in my life, let alone call anyone a slut. "You are my hot little slut, aren't you?"

She arched her back and turned to look at me. Our eyes met as she said, "Yes, I'm your dirty little slut. Just don't stop fucking me."

I just gave it to her hard, my hands gripped her hips and I pushed it in hard and fast. No romance just a hard fucking. Her body gave out and collapsed on the bed, this made it easer for me to get deep access to her pussy. With each thrust Linda was pushed deep into the bed as I just focused on using her for my own pleasure.

She gasped and whimpered as she neared cumming. "I've never had it this hard before or this long! I'm going to cum....please don't cum yet, oh god, you're making me cum!"

Linda's body tightened as she approached her orgasm, she let out a soft scream, and her fingers dug into the comforter. She pulled the comforter down closer to her as her orgasm hit like a truck smashing into a brick wall. Her body shook and convulsed as she was lost in her own little world. I just kept my cock deep in her to give her pussy something to gripe.

She took another minute or two to come back to me, her eyes opened and smiled. "That was freaking awesome. I've never experiences anything like that before!"

I pulled out allowing her to move up on the bed. She watched me as I moved up next to her, her eyes glued on my glistening cock. Linda smiled as I moved between her legs as I wasn't finished with her just yet.

She opened her legs giving me access to her pussy and I moved in and on that. My cock easily slipped back into her as her juices were everywhere. She let out a moan as I pushed my cock into her. My hands moved down to her legs and I pulled her legs up and around me. My forearms went under her knees and her feet rested on my back. From this position, I could tear her box up and slowly started to do just that. Part of me was hoping that she would cum again as then she would crave me in her bed.

Faster and faster I worked my cock until I could feel my orgasm start to approach. "Oh, you feel so hot and wet! I'm love how you make my cock feel."

"Do you? Do you want to cum in me? Come on baby, cum in me. I want to feel it, will you cum in me?"

I love hearing her talk dirty as its so kinky turning Linda into a slut. Her talking was kind of erratic and she had that look in her eye. That look that says, I'm going to cum again weather you like it or not. There was no way that I could take it easy now just prayed that I could hold out long enough.

"Oh baby, I'm cumming again." She grunted.

That did it for me; one hard deep thrust and I started to shoot my load into her! I'm cumming in her! Feeling her pussy clamp down on my cock just sent me over the edge. Oh it felt so hot to cum in her!

Once finished, I rolled off her. My cock glistened mostly from her pussy but there were a couple globs of cum. We laid there, not speaking and not moving just basking in the moment.

Linda snuggled up next to me, "That was so out of this world. I've never cum twice in one night."

"I'm glad that you enjoyed it, your one amazing woman."

She reached over and cupped my balls and squeezed my cock. "A girl could get use to this thing."

My cock started to harden in her soft hand.

She kissed my chin, "This has to be our little secret," she said as she rolled on top of me.

"Of course, I promise." She guided herself onto my cock and rode me hard and it seemed that she was a very happy woman that night as that was just the start of our sexy journey together.