Seduced by Best Friend's Mom Pt. 05

Vanessa walked into the house after our sexcapade by the pool. I followed her, admiring her incredibly, sexy ass from behind. She stopped when she reached the foot of the stairs and turned to face me.

"Where do you think you're going?" She asked, making me stop dead in my tracks.

"I was going to follow you up to your room. I figured we could go for round two."

"You figured wrong. Right now, I'm going to take a shower and take a nap."

"You know what, that's a good idea. I should freshen up and take a nap too. Your mom will be home in a few hours. I need to be well rested before I have my way with her tonight." I said with a smirk.

Vanessa puckered her lips and squinted her eyes a bit. I think my little comment made her jealous. She turned her back to me and placed her right foot on the bottom step, her left foot remained on the floor. She turned her head and looked back at me, over her right shoulder. She slipped her right index finger into her mouth and sucked on it, sensuously.

"FYI, I have an itch I need help scratching." She said after she took her index finger out of her mouth.

She lowered her finger down and around to her backside. She slipped her finger into her semi-exposed rectum and ran her lubricated digit up and down her anus.

"Don't over exert yourself tonight. If you do, I may have to ask my soon to be ex-boyfriend, Jason, to do the honors of scratching this itch."

Vanessa turned and started walking up the stairs. She walked very slowly, almost methodical. She knew I was watching her. It took every ounce of self control I had not to bend her over and have my way with her. I had to be patient. I knew it was just a matter of time before my cock penetrated her rectum the same way I had penetrated her mother's asshole. I watched her until she reached the top of the stairs and disappeared around the corner.

I walked into my bedroom and grabbed a fresh pair of shorts and a tee shirt. I decided not to bring a pair of boxer briefs with me in case an opportunity presented itself where I needed easy access to my cock. I walked into the first floor bathroom and washed up. After my shower, I crashed on the couch in the living room. It didn't take long for me to fall asleep.

I woke up, startled, struggling to breathe. I tried inhaling, but couldn't.

"Anthony. Wake up!" John exclaimed, looking down at me.

Vanessa stood by his side. They were both chuckling. John was pinching my nose and Vanessa pressed her hand over my mouth. I sat up and pulled both their hands off of my face.

"Assholes!" I yelled at them.

Their laughs got louder and more hysterical.

"What are you two clowns laughing at?" I asked.

John stood up and pointed down at my crotch. My shorts were raised on the left side of my thigh and I saw the tip of my penis sticking out. I looked up at the siblings, roaring at me with laughter. I covered myself up, embarrassed. I could feel my face get hot. John kept snickering. Vanessa licked her lips and winked at me.

"Cut it out you two." I heard Jessica's voice say. "Anthony, it's time for dinner."

I sat up, took a few deep breaths and calmed myself. Once my face cooled, I got off the couch and followed John and Vanessa into the kitchen.

"Hi Jessica." I said to my friend's mom.

"You look tired." Jessica said with a twinkle in her eye. "What did you do today?"

"John and I played basketball with the guys earlier and I didn't sleep much last night."

I saw Jessica and Vanessa both look at me. They both knew why I didn't sleep much the night before. Jessica had no idea Vanessa knew we slept together and Jessica had no idea I had fucked her daughter earlier that afternoon. I felt a sense of excitement build up in the pit of my stomach.

"I know when I take afternoon naps, I always have a hard time sleeping at night. What will you do with yourself if you can't sleep later?" Jessica asked with a wink.

"I'm sure I'll find something to do with myself until I get tired."

I noticed Vanessa squint her eyes at me as she sat down at the dinner table. She knew what I was implying. I sat down between her and her mother. Jessica told us about her day. She had sold two houses, which was exciting. After dinner, Jessica placed a box of frosted cupcakes on the table.

"Who wants dessert?"

"Whoa, those look really good!" I exclaimed.

"Yeah they do." Said john as he grabbed a chocolate frosted cupcake.

"I picked them up from the local bakery on my way home. I know my boys love cupcakes."

Jessica always called John and me 'her boys'. Vanessa skipped the cupcakes. John and I had two each and Jessica had one. When we finished eating, John and I went up to the game room and shot some pool. Vanessa helped Jessica clean up and they stayed downstairs, talking. It was 11pm when Jessica called up to us to wish us a good night. Vanessa walked by us shortly after and walked toward her room. John stopped her before she closed the door.

"You want to go to the beach with us tomorrow? I'm picking up Josie and her sister may go too."

"Sure." Vanessa said.

"Do you want to invite Jason?"

"I broke up with Jason earlier today."

"What? What happened?" John asked.

"He's just not the right guy for me. Besides, I'm too busy for a boyfriend right now. I don't need to be tied down."

"Shit Vanessa. He was a cool guy. That's too bad."

I felt a bit of guilt in the pit of my stomach. Jason was a cool guy and I fucked his girlfriend earlier. Vanessa made it clear to me when we were by the pool that she wanted me to be the guy who who took care of her sexual needs and that she didn't need a boyfriend. I looked at Vanessa and she looked at me. I think she felt a bit guilty too.

"He is a cool guy, but I don't want to waste his time or mine. Why should I keep dating someone when I know inside he isn't the one for me?"

"Alright then." John said, dropping the subject.

"What time are you planning on leaving for the beach?" Vanessa asked.

"Not too early. Probably around ten or eleven."

"Ok, I'll be ready by then. Good night boys." She said as she closed the door to her bedroom.

"Wow, can you believe she broke up with Jason?"

"No. I'm as surprised as you are." I lied.

"That came out of nowhere too. They looked all lovey dovey last night when we all hung out and then BAM, it's over. I wonder if something happened between them at work today."

"No idea." I lied again.

I knew exactly why Vanessa broke up with Jason.

"I'm going to be after this game. John said. "Josie tired me out at her place."

We both laughed and I gave him a fist bump. We finished our last game of pool before heading our separate ways. John walked toward the bathroom and I walked down the stairs and into my bedroom. I stood by the doorway and waited, listening for John. I waited patiently until I heard the bathroom door open and his bedroom door close. It was almost midnight. I rushed across the house, down the hallway that led to Jessica's bedroom. I heard the t.v. on in her room and knocked on the door.

"Yes?"

"It's me."

"Come in Anthony."

I opened the door and found Jessica on her bed. She had a short, red satin nightie on. The bottom of her nightie rested on her abdomen. Her legs were spread and a magic wand hummed over her clit. I froze where I stood and watched as Jessica massaged her nub with the vibrating head attached to the wand.

"You like what you see?" She asked.

"No." I said.

Her smile turned into a frown.

"I don't like it, I love it." I added.

"Smartass! Keep busting my balls and I'll make sure I'm the one that gets the last laugh."

"You better not have balls." I said sarcastically.

I closed her bedroom door behind me. Jessica bent her knees and placed her feet flat on her bed as I walked to the foot of the bed to get a better view of what she was doing. Not only did I get a good view of Jessica's bush, I saw a familiar string and white ring sticking out of her hairy asshole. Her pubic hair was matted and wet.

"You got started without me?" I asked.

"Let's just say I am getting warmed up for you."

I stripped down as fast as I could and jumped up on the bed. Jessica giggled at my enthusiasm.

"Do you mind if I handle this wand for you?"

"All right." She said, handing it to me.

I took the wand from her hand and lowered my face in between her legs. I kept the wand pressed onto her love button, but moved it a bit so that I could get my tongue into the inner folds of her pussy lips. Her wet pubes tickled my nose. I licked up from the bottom of her slit to just below the the vibrating head on the wand. My tastebuds awoke as I savored Jessica's tangy nectar. She sighed deeply when she felt the flat surface of my oral muscle slide up her womanhood. I moved my tongue up and down very slowly, methodical in how I pleasured her. Jessica's hips twisted and wriggled at the multiple sensations she felt from her vagina and hooded nub. My tongue zigged and zagged over her soft, pink pleasure zone. I traced numbers and letters on her perineum, shifting down to her anus and up to her slit. Within minutes, Jessica's whole body spasmed and convulsed on the bed. She clasped her thighs around my ears, as her pelvis squirmed and trembled from her climax. I kept my head and neck loose so that I could mimic her movements and not get my neck twisted and broken. It got to a point where I grabbed the ring sticking out of her ass and pulled on it hard, making three beads pop out of her asshole. Jessica released her grip on my head and almost slid off the bed.

"Dammit Anthony, I can't control myself when you make me cum!" She exclaimed. "How do you do that to me?"

"Trade secret." I said with a wink.

Jessica sat up and re-adjusted herself on the bed. She grabbed the magic wand and turned it off. Then she got off the bed and walked toward the bathroom.

"Don't move. I have to pee. I'll be right back." She said, looking back at me.

I was disappointed. I was hoping she would invite me into the bathroom with her. Instead, I sat on the bed and watched as the three beads hanging from her ass swayed back and forth as she walked. When the door to the bathroom closed, the bedroom door swung open, scaring me half to death. Vanessa stood in the doorway, looking at my naked body. She had a small, white half tee shirt on and a pair of grey, cotton shorts. Her nipples were hard beneath her shirt.

"What the fuck Vanessa!" I exclaimed softly.

She put her index finger over her lips and shushed me. She stepped into the bedroom and closed the door behind her. She ran over to the bed, grabbed my hard cock and licked the tip. Then, she got down on the floor. I laid down on my stomach and looked at her from the edge of the bed.

"What are you doing? Are you crazy?!"

She smiled at me and slid under the bed, out of view. I heard the toilet in the bathroom flush. I readjusted myself and laid down on the bed. My heart was racing. I was petrified of what Vanessa was about to do. Within moments, the bathroom door opened and out came Jessica, completely nude. She had taken off her satin nightie. The string of anal beads was nowhere to be seen as she walked.

"I have a surprise for you." She said as she approached the bed with her hands behind her back. "Close your eyes Anthony."

"I don't know Jessica." I said, more afraid of Vanessa jumping out from under the bed than I was of what Jessica had planned for me.

"Fine. If you don't want to close your eyes, I'll turn off the lights and t.v.

Jessica walked over to the lightswitch on the wall and flipped it off with her elbow, careful not to show me what she had in her hands. Then she walked over to the nightstand where she had the remote control for the nightstand. She lifted up her leg and pressed the power button with her big toe. She gave me a closeup view of the long pubes on her crotch before the t.v went off. It was completely dark in the room. She had the blinds in the windows down, so any natural light from the outside barely permeated through the sides of the blinds. I heard something drop onto the nightstand and then I felt her warm, soft body get into bed with me. I felt one of Jessica's hands touch my left shoulder. She slid her hand down to my chest and leaned into me. I felt her hot breath in my left ear as she slipped my earlobe into her mouth. Her soft breasts pressed into my shoulder.

"Your heart is pounding." She said, as she lay her hand, flat, on the left side of my chest. "Are you excited or nervous for what I'm about to do to you?" She asked.

"Both." I lied.

I was more nervous about Vanessa and her intentions.

"Don't be nervous Anthony. I won't do anything to you that you wouldn't do to me." She whispered as she sucked my earlobe back into her mouth.

I felt my heartbeat increase. It was thumping in my chest. There were a lot of things I wanted to do to Jessica, and once I thought about it, some of them were not things I was ready to have done to me.

Jessica started kissing the side of my neck, down to my shoulder and chest. Her soft lips felt wonderful on my skin. She found my left nipple and began to suckle on the hardening tissue. I got goosebumps throughout my body. She took her time kissing, licking and caressing my torso. Within minutes, my heartbeat returned to normal. I stopped thinking about Vanessa and focussed on the sensations Jessica was making me feel. Vanessa hadn't made a sound up to that point, so I felt more relaxed.

"Anthony, I want to do 69 with you, but I want you on top of me."

"Whatever you say beautiful."

I sat up and felt jessica lay down next to me. The king sized bed gave us plenty of room to move around. Once Jessica was on her back, I flipped around, onto my hands and knees and climber over her, letting her hands guide me to where she wanted me. Once I was in position, I lowered my face into her inner thighs and began licking her hooded nub. I swirled my tongue around her long pubic hair as I fondled her clit. I felt Jessica's hands on my ass, caressing my backside. She took my penis with one of her hands and put it to her lips. I felt her tongue lick my pee hole and the sensitive area under the tip of my cock. It felt so good. She held my cock firmly with one hand, occasionally slipping the entire glans into her mouth, sending shivers up my spine. She knew exactly how to work my cock. There were times where I just lay the side of my face on her pubic hair and savored the pleasure she made me feel. After a while, Jessica's hands shifted beneath me. I felt her reposition her body until I felt my balls in her mouth. She licked and suckled them gently, making sure she was careful not to hurt me Then, without warning, I felt her wet, firm tongue slip into my rectum. I clenched my ass cheeks reflexively, but she used her hands to pry them apart. It was an odd, yet pleasurable sensation, something I had never felt before. Once I got used to the feeling of her tongue in my ass, my glutes relaxed. The more she licked my anus, the more I enjoyed it. I felt her left hand move and I heard a noise on the night stand.

"What are you doing Jessica?" I asked.

"Shhh. Relax Anthony. You are going to enjoy this. Trust me."

I felt her hands shift around my ass and her tongue moved back down to my balls. I felt my ass cheeks get pushed apart and then something firm and cold pressed against my taint before it penetrated my anus. I lunged forward, trying to get away from the object that she was trying to violate me with. It was a futile attempt as Jessica pushed the object deeper inside me. I flipped over and laid on my back. Jessica was quick to get up and move with me, barely losing her grip on the cold, hard apparatus she inserted into my backside. I clenched my glutes and thighs, pinning her right forearm in between my legs.

"Relax Anthony." She said. "The more you relax, the better it will feel. When I'm done with you, you will beg me to do this to you again."

I continued to struggle but Jessica was relentless. Eventually, my rectum adjusted to the pressure I felt inside me and I started to relax a bit.

"What did you put inside me?" I asked.

"It's a small butt plug."

"A butt plug?"

"I figured you had a virgin ass so I got you the thinnest butt plug I could find. Just do what I tell you and you will see how good it can feel."

"Fuck Jessica, I had a really weird feeling when you pushed that thing inside my ass."

"Now you know how I feel when you push and pull those anal beads out of my ass."

"Touche." I said.

"Now, sit up on the bed."

I did as she told me and sat on the bed, which kept me from pushing the plug out of my asshole. I felt Jessica straddle me. She sat her ass on the edge of my lap, while facing me. Her left hand was around my neck. She took hold of my erection and shifted her body until her pussy engulfed my stem. Once my cock was inside her, she wrapped her legs and arms around me and embraced me. She held me tight. I wrapped my arms around her lower back and she leaned in to kiss me. We made out as her hips gyrated slowly, back and forth on my lap. The force of her lower body rocking back and forth on my lap made my lower body rock back and forth on the bed. I felt the butt plug inside my anal cavity moving around. The sensation I felt was indescribable. It was odd at first, but it became intense and pleasurable as we fucked.

"Oh my god Jessica. This is such an odd sensation. I feel the plug inside me moving around while you fuck me and it feels really good. I don't know how to describe it."

"Are you enjoying it?"

"I am but I'm not sure I can last very long if we keep going like this." I warned her.

"That's because the butt plug is massaging your prostate. It's meant to help make you cum. Don't worry about how long you last. I just want to make you feel good. Do you want me to stop or do you want a release?" She asked as she kissed my lips.

"I want you to make me cum, Jessica."

"Ok Sweety. Momma's gonna make you cum inside her pussy."

Something about those words triggered my climax, instantly. She had been like a second mother to me for as long I could remember and my sexual relationship with Jessica definitely felt like taboo. It was such a turn on for me.

Jessica's hips started grinding me faster, causing the butt plug inside me to massage my anal walls harder and faster. I tried to hold out a little longer, but I couldn't. I felt myself ejaculate inside her. I hugged her as tight as I could and thrust my pelvis up into her from my seated position. I wanted my seed deep inside her.

"That's it baby. Cum inside momma. I can feel your cum deep inside my pussy." She whispered into my ear.

We locked lips again and held each other for quite a while. Eventually, I went soft and her vaginal muscles pushed me out of her muffin. I felt my semen leak out of her and down my scrotum.

"Do you think you can handle a thicker butt plug next time?" She asked as she got off my lap.

"Give me some time Jessica. It's something you have to ease me into."

"Ok baby. We will go at your pace. I'm glad you are open to the idea and you enjoyed what we just did."

"I enjoyed it very much."

We kissed each other again. Then, I got out of bed and turned on the light. I was about to go to the bathroom when I looked down onto the floor and saw Vanessa's head peek out from under the bed. I had completely forgotten she was under there. She looked at me with a big smile.

"What the hell was she thinking?" I thought to myself.

"Do you want to go wash up with me?" I asked Jessica as I walked toward the bathroom.

"No, I'm ready to go to sleep." She said as she slid her right index and middle fingers over her pussy lips.

I saw the creamie I left inside her ooze out of her vagina. She took her cum soaked fingers and put them in her mouth.