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A friends mom5 Years ago, my best friend John and I graduated from high school. We had known each other since 1 st grade and we became like brothers as we grew older. John lived with his mother Jessica and older sister Vanessa. His mom and dad divorced when he was 7 and Jessica never remarried. Jessica and my mom were also best friends. They had met 11 years earlier at a group for divorced moms with k**s. My mom and dad had also divorced around the same time as John’s parents. Jessica and my mom started hanging out when they learned that John and I went to the same school and over time, we all became very close. I was an only c***d and I spent a lot of time at John’s house over the years, since my mom traveled a lot for work. Jessica became like a second mom to me.Two weeks after high school graduation, my mom had to go on a long business trip overseas and I stayed at John’s house during this time. John and I had big plans for that summer, considering the fact that we were going to go to different colleges and we wouldn’t be able to hang out much once we started the next chapter in our lives. Little did I know that not only was I about to have the best summer of my life, I was about to have the best experience of my life. Jessica was a well known real estate agent in the Tampa, FL area, where we lived. She was very successful and she had a beautiful home. I enjoyed spending time at her house. She had a 4,000 sq. ft. home in a great neighborhood, with a built in home theatre and a game room with a pool table, ping pong table and a couple of retro arcade games. John and I spend a lot of time in these rooms, or outside, by his pool. The pool area was great. There was a huge privacy wall, so none of the neighbors could see back there. There was also an outdoor hot tub and cabana. Jessica was cool and she would let John have friends over for pool parties all the time. One day, John and I were hanging out by the pool with his girlfriend Josie and his sister Vanessa. I wasn’t seeing anyone at the time. We were talking and listening to music when Jessica came out to join us. She said hi to everyone, and proceeded to take off her robe to sit one a lounge chair on the opposite side of the pool from where we were. My eyes almost popped out of my head when she took off her robe. Jessica was not very tall, probably 5’3″. She had straight, dark brown hair with blonde highlights, sky blue eyes and tanned skin. Over the past year, Jessica had started working out and she had lost at least 40 pounds. I had seen her a bunch of times in a bathing suit, but she always wore a one piece and some kind of dr****g around her waist. This was the first time I had seen her in a bikini. She looked amazing. Her arms and legs were toned, she had nice, c-cup breasts and an thin, hourglass shape. Her breasts sagged a little, but they still looked good in here bright yellow bikini top. I couldn’t stop looking at her. I always thought of her as a second mother, but my perception of her changed that day and I began lusting for her. I couldn’t explain why, but I did.After Jessica sat in the lounge chair, she reached over to a small table, next to her and grabbed a bottle of sun screen. I watched her spread the white, creamy lotion on her shoulders, arms, chest, stomach and legs. It was a good thing I had sun glasses on. I continued my conversation with my friends, but my eyes never left Jessica. Once she was done spreading the lotion over her body, she sat back in her chair, put on her sunglasses and laid back to soak up the sun’s rays.About an hour later, Vanessa left the pool, to get ready to go meet her boyfriend. She walked over to her mom, said a few things to her and gave her a kiss on the cheek. Jessica sat up and asked us if we wanted some lunch. John and his girlfriend said yes and they got up to go in the house to change out of their bathing suits. They said they would go grab some take out for us. I decided to stay in the pool for a while longer. After everyone left, Jessica got up from her lounge chair and looked over at me.”How’s the pool Anthony?””It’s great Jessica.” I replied, staring at her behind my sunglasses. John’s mom had always insisted I call her by her first name.”Good. I need to cool off a bit. The sun is hot today.”Jessica walked over to the diving board and plunged into the pool, head first. When she emerged from the water, she swam over to the shallow end, where I was standing. “Have you talked to your mom?” She asked when she approached me. She stood up, looking at me and waited for my reply. My eyes just moved down to her breasts. The water was glistening off her smooth, tanned skin. “Not since yesterday morning.” I replied, forcing myself to look up at Jessica’s face. I noticed a slight smile.I felt my face get very warm. I wasn’t sure if I was blushing or it was the sun making me get hot. I hoped she didn’t notice me looking at her chest. “Well, I spoke to your mom this morning, before coming out to the pool. She told me she needed to stay away on her business trip for a couple of extra weeks, so it looks like you will be spending some extra time here. She said she would call you tonight with the details.””Ok.” I said. Still feeling embarrassed at the idea that Jessica may have caught me looking at her breasts. “You are not very talkative today Anthony. You feeling OK?” She asked as she splashed some water in my face.I started laughing and splashed water back at her. Jessica was always cool with us k**s. She was 45 years old, but she acted like she was 20 sometimes. She was very playful and very full of energy, especially since she had lost all her weight.”I’ll race you to deep end and back. Loser has to take a cold shower in the outdoor shower by the cabana.” Then she splashed me again in the face and took off, swimming toward the deep end of the pool.I tossed my sunglasses over my head and swam as fast as I could after her. The outdoor shower had no hot water and it was always cold. I hated cold showers. Jessica and I reached the deep end at the same time, and raced back toward the shallow end. I was captain of the varsity swim team at school. Even though Jessica had a big lead to start, I easily caught and passed her, beating her by several strokes to the end of the race. I got out of the pool and stood at the edge, with my arms crossed, looking down at her. She reached the end and looked up at me, breathing hard.”What took you so long?” I asked, teasing her.”Funny guy.” She said sarcastically. “Help me out of the pool.” She demanded, extending her left arm up at me.I bent over to help pull her up, but instead, she grabbed my arm and pulled me in. I dove right canlı bahis over her. When I came up, she was wading through the water, toward the ladder to climb out. I chased after her and reached the ladder as she stepped up on the last rung. I looked up at her and saw her bikini bottom wedged in between the crack of her round ass. I could see the tan lines where her skin went from bronze colored to almost milky white. I also saw something else I didn’t expect. I saw a slight patch of dark, pubic hair sticking out of the left side of her inner thigh.”That’s what you get for not letting me win!” She exclaimed as she laughed, running over to the shower by the cabana, while pulling her wedgie out of her ass. I climbed up the ladder and ran after her. She turned on the shower and put her hand under the running water. “Fuck!” She squealed. “This water is cold!”I put my hand under the water to feel how cold it was. She was right. It was really cold.”Karma is a bitch Jessica.” I said as I grabbed her and pushed her under the water.She squirmed and tried to pull away, but I held her tight. It felt nice holding her body against mine as she squirmed and pressed up against me. At one point, I wound up behind her with my arms wrapped around her waist and my crotch pressed up against her ass. Oddly enough, Jessica didn’t struggle to get free as much when I was pressed up against her. It actually felt like she was pressing her hips into my crotch. My heart beat sped up and I felt my manhood swell up a bit. I pulled away from her because I didn’t want her to feel me get hard.”We made a bet and you lost. Get in the shower Jessica, before I lose all respect for you.” I joked with a chuckle.”Fine, but I will pay you back for this.””Yea, yea. You are the one who bet me and lost.”Jessica gave me a puppy dog frown and walked under the shower head. Her whole body quivered and she squealed as the cold water hit her skin. I just stared at her and admired her body. Her nipples started to protrude from her bikini top and I could see goosebumps pop up all over her skin. “Don’t just stand there staring boy, go grab me a towel!” She exclaimed in a high pitched voice. I laughed and walked into the cabana and grabbed a towel. “Here you go Jessie.” I said calling her by her nick name.She jumped out from under the shower head, grabbed the towel, and wrapped her self in it. She was shivering where she stood. “Oh my God, this towel is so warm.” She said, a look of ecstasy on her face. I walked over to the shower and turned the water off. Then I went into the cabana and grabbed 2 more towels. I walked behind Jessica and put a second towel around her shoulders. “I already have a towel around my shoulders dumbass.” She said defiantly, obviously annoyed that I made her pay the consequences of losing our bet. “Wrap that towel around my waist.”I stood in front of her, reached around her waist, grabbed the towel from around her and brought the 2 ends of the towel to her belly button. I tighten the towel around her and slipped one end in behind the other, my hand pressed between the towel and her lower abdomen. An image of me unwrapping the towel and taking of her bikini bottom popped into my head and I felt my manhood swell again. A let go of her towel and quickly wrapped the other towel I grabbed around my waist. I noticed another smile on Jessica’s face.”I’m going inside to take a shower. John and Josie should be back soon with lunch.”Her voice snapped me out of my fantasy world and I walked into the house behind her. She walked toward her bedroom and I walked toward the guest room bathroom.After my shower, I walked out toward the kitchen and saw Josie and John eating their sandwiches. I grabbed a sandwich and a drink and we started. We were just about finished when Jessica walked out, wrapped in a long, white, cotton robe. “Dam mom, it’s like 90 degrees outside and you are all bundled up. You feeling ok?”Jessica looked at me and we gave each other a slight grin. I hadn’t told John about the little game Jessica and I had just played. “I’m fine John. I have a chill. The AC is on high and it’s cold in the house.””Whatever you say mom. Ant, you wanna go catch a movie with Josie and me?””Nah man, you guys go. I’m gonna stay in tonight.””What the hell is wrong with you? Vanessa and her boyfriend are gonna meet us. Then we are going to hang out a Jimmy’s house.”Jimmy was another close friend of ours. Normally, I would have said yes, but I wanted to spend more time with Jessica. I had the urge to be around her, any chance that I got and I had a cool vibe with her that day. “I’m not in the mood. I’m not feeling so hot right now. I’m going to take a nap and if I feel better later, I’ll catch up with you guys.””Alright bro. Feel better.”John and Josie got up from the table. John kissed Jessica on the cheek and they left. Jessica walked over to me, bent over and placed her hand on my forehead.”You don’t have a fever. You feeling ok?”I looked straight ahead as she placed her hand on my forehead, and Jessica’s chest was at my eye level. When she bent over, the top of her robe dropped down. She didn’t tighten the sash around her belt very tight and it hung loosely from her body. I could see her breasts drooping down on the inside of her robe and I noticed she didn’t have a top on. Jessica caught me staring, but she didn’t move. She smiled at me. “Do you need me to take care of you Sweety?” She asked.I finally looked up at her and saw a funny look in her eye.”Yea, I think I may need to be taken care of.””Hmm. Well, we need to figure out what is wrong with you so we can figure out the best course of treatment for you.”Jessica stood up, took my hand and pulled me up. I stood up and looked at her. She still had that funny look on her face, a look I had never seen before.”Follow me.” She said as she held my hand while we walked down the hallway into her bedroom.I couldn’t remember the last time I had been in her bedroom. I was probably 10 years old. I used to hide in there all the time when John, Vanessa and me played hide and seek. “Sit on the bed. I need to go get my first aid kit.”I did as she said and watched her walk into her bathroom. Moments later, she came out with a small case. I noticed the sash on her robe seemed to hang more loosely than it did when she walked into the bathroom. “Lay down Sweety.” I did as she asked. Then she opened up her case and pulled out a thermometer. She sat on the bed next to me, facing me. She bent her left knee, placed it on the bed toward me and kept her right leg on the floor. Her robe opened quite a bit and when she sat down. All I could see was tanned skin as she exposed bahis siteleri her inner thighs to me, but not high enough for me to see that special place between her legs. “Open your mouth for me.” She said in a soft voice. I did as she asked and she leaned forward and placed the thermometer in my mouth, under my tongue. I was feeling warm and I started to sweat a bit. My heart was beating fast again. My eyes were glued to her lower body. Jessica placed her hand on my forehead again.”Oh my Sweet, are you hot? You are starting to perspire a bit.”I looked up at her and nodded. “I think you should take off your shirt. Sit up.”Jessica shifted her body and she slid her knee closer to me to balance herself before she stood up. When she shifted her knee, I saw what looked like a dark patch hair between her legs. Had I just seen what I thought I saw? Is Jessica completely naked under her robe? My heart was pounding now. What is happening? I asked myself.I sat up and Jessica grabbed the bottom of my shirt and pulled it over my head. Then she pushed me back down, indicating that she wanted me to lay down again. I laid back down and Jessica sat back down next to me, in a similar position to where she was moments ago. My head shift south again. The more Jessica moved around, stood up and sat down, the more the sash on her robe loosed. She either didn’t notice or she didn’t care. When I looked down toward her inner thighs again, I had a perfect view of what she had between her legs. I could see a large, dark patch of pubic hair. I started getting aroused and I felt my penis grow under my basketball shorts. I had nothing to cover myself up with, but I decided not to even try. Jessica placed her hand on my chest as she leaned over to pull the thermometer out of my head. The top part of her robe opened up when she leaned into me and her left breast was almost completely exposed. Her nipple was still covered, but barely.”Anthony, your heart is pounding.” She said as her left hand rested on my chest. “Your face is flush too. Are you nervous?”I shook my head side to side. My penis continued to swell in my shorts and a noticeable tent appeared below my waste. My eyes kept shifting between Jessica’s exposed crotch and her protruding breast.”I’m going to get you a cold wash cloth. Your starting to feel very warm and your beginning to sweat.”Jessica stood up and turned to walk toward the bedroom, but stopped when she noticed the tent in my shorts. She turned and looked back at me, a big smirk on your face. “I see what’s happening here. Now that we know what the problem is, I think we can start your treatment. Do you want me to treat your ailment?” She asked, looking at my crotch.I just nodded my head. I felt like a shy, little k**, afraid to talk to a stranger. Jessica felt like a stranger. I had never seen this side of her, nor did I ever imagine I would see this side of her. She was acting very differently and I loved it. My cock was throbbing inside my shorts. I wanted to ravish my best friend’s mother, but I restrained myself and waited to see what she had in mind for me. “Ok Sweety. I have the perfect cure for your ‘ailment’. The first thing we need to do is to cool you down. We need to take off these shorts. I sense a lot of heat being generated down here.”She bent over and grabbed the sides of my shorts. When she bent over, her left breast popped out of the side of her robe and was completely exposed. Her left nipple was fully erect and stood about a half inch. My cock ached to be exposed and within seconds, Jessica pulled off my shorts and boxer briefs. My manhood saluted Jessica after she pulled my shorts and underwear off. “Oh my Anthony. You sure have grown.” She said in a sultry voice, eyeing my meat. The sash of her robe had come undone when she worked my clothing off and her robe hung open in front of her. She didn’t even try to cover herself up and proceeded to flash her hairy pussy at me. She had long pubic hair and her muff was shaped like a large triangle. My cock was so hard at this point. The tip of my penis was so engorged and swollen, causing it to turn purple.Jessica sat on the bed again, in the same position she had the last 2 times and looked at me. She placed her left hand back on my chest and her right hand on my left cheek. “Are you ready for your treatment?” She asked as her left hand moved down my chest, toward my stomach. “I am more than ready.” I said, finally able to speak.Jessica’s hand kept moving south. I started getting goosebumps. I wasn’t a virgin, by any means, but it had been over 6 months since I had sex. I felt Jessica’s hand reach my pubic hair. She spread her fingers and ran them fingers through my pubes, sending what felt like electricity throughout my body. Her hand continued to move south, but she bypassed my hardness and went for my balls. I spread my legs and she cupped my testicles in her hand. She massaged them very gently and the electricity I felt earlier intensified. I raised my right hand and cupped her left breast. Jessica let out a little gasp when I touched her breast. Her nipple had softened from when I first saw it, but it hardened quickly when I touched her. I massaged her breast and pinched her nipple, ever so slightly. When I did this, Jessica’s left hand stopped massaging my balls and moved toward my shaft. I felt her wrap her warm fingers around my girth. She started rubbing me slowly, stroking my stick. My body shuddered to her touch. Jessica’s eyes were focussed on my face. She never looked back at my cock. I started thrusting my hips up and down ever so slightly while she stroked the length of my penis. I sat up a bit, grabbed both sides of her robe with both my hands, and opened it. I pulled her robe back so that it dropped off her shoulders and down her back. Jessica sat in front of me with both her breasts fully exposed. They were gorgeous. They drooped a bit but her nipples were extremely perky. Her tan lines were totally exposed and made her look sexy. Her breasts were milky white and soft. I massaged both of them with my hands. Jessica arched her back and pushed her chest forward as I caressed her tits. Her grip tightened around my shaft and she began stroking me faster. It didn’t take long before I announced I was about to cum. As soon as I said this, she pinched the tip of my cock with her thumb and index finger and squeezed hard. I felt a pressure build up inside of my cock, but I couldn’t release it. Jessica stood up and her robe dropped on top of the bed. She spun around, bent over and released her grip. As soon as she let go, she wrapped her lips around my purple helmet and began stroking me bahis şirketleri again with her right hand. I erupted within moments and I felt spasm after spasm shoot from my balls and up through my shaft. I could feel rope after rope of cum shoot from the tip of my cock into Jessica’s mouth. While Jessica worked my cock with her lips and her hand, I slipped my hand in between her legs, up toward her pussy. I ran my fingers through her soaking wet pubic hair until I felt her smooth slit. Jessica swallowed my cock when I touched her pussy and her thighs closed around my hand. I tried to slide a finger inside her but she squeezed her thighs tighter. My body convulsed as she bobbed her head up and down on my shaft. The tip of my cock was very sensitive after cumming in her mouth. I begged her to stop. She did as I asked, and she started kissing and licking my balls. I pulled my left hand out from between her legs and put it on her ass. I put my right hand on her ass too and spread her ass cheeks. I could see a strip of pubic hair run up from between her thighs, into her asshole. I loved seeing her like this. I had never been with a woman as hairy as Jessica. I had been with 3 girls up to that point and they were either shaved or had very little pubic hair, because they trimmed themselves. It was a real turn on to see a woman such as Jessica in her all natural state.”I think it’s time to give you phase 2 of your treatment.” Jessica said as she took her lips off my cock. She stood up and climbed up onto the bed. She swung her left leg over me and straddled my chest. Then she looked down at me for a moment, before speaking. I looked up at her, enjoying the view of her breasts.”I’m going to give you something to eat. It will help make you and me feel good.”She shifted her body closer to my face until her crotch was hovering above my face. I looked up at the pubic hair hanging from her pussy. It was drenched and glistening in her juices. I put both my hands on her ass and she lowered herself onto my face. Her wet pubes drenched my face and nose and I slipped my tongue into her hairy muffin. I felt my tongue slide over a small, hard nub that made Jessica moan. I knew I found her clit. I started sucking and licking her nub and within moments, she was grinding her hips over my face. I felt my chin and neck get very wet as her pussy produced excessive amounts of fluid. I licked and sucked her faster and harder, which made Jessica squirm and grind my face with more intensity. I took my hands off her ass and grabbed both her breasts. She arched back and placed her right hand on my right thigh, while her left hand grabbed my head and pulled it up, deeper into her pussy. I had to hold my breath because I couldn’t breathe and then, out of nowhere, Jessica let out a loud, orgasmic scream and announced she was cumming. I felt fluid drench my face, neck and chest, as streams of her warm cum soaked me. I had never experienced anything like that with any of my past girlfriends. I started tapping her hips and trying to push her off my face, because I felt like I was going to suffocate in her pussy. I couldn’t hold my breathe any more. Jessica fell back and laid down on top of me. Her head was on top of my cock and her legs were on either side of my face. I propped my head up a bit and spread her pussy lips with my hands, finally getting an opportunity to see her pink slit. This made my cock swell up again. Jessica’s body was still trembling a bit after her orgasm. She lifted her head when she felt my penis harden against the back of her head. “I guess you are ready for phase 3 of your treatment.” She said softly. “It’s time to make you sweat again.”Jessica got off of me and told me to stand up. I did as she asked. She repositioned herself and laid down on the bed, in front of me. She told me to stand in front of her, close to the bed. I moved to where she told me to go. She lifted up her legs and propped her feet up against my shoulders. “I want you to put that big cock of yours inside me.” She commanded. She didn’t have to ask me twice. She opened her legs for me and I took hold of my shaft. I slipped the tip of my penis into her bush. She spread her pussy lips with her hands, and exposed her slit. I rubbed the tip of my cock over her clit a few times and her body convulsed. Her clit was still sensitive from the oral pleasure I had given her. I did this a few more times until she begged me to put my manhood inside her. I couldn’t resist her anymore and I pushed the tip of my cock inside her warm, wet hole. I pressed my thighs into her and the entire length of my shaft slid right in. Her pussy was so wet, yet tight. It felt amazing. I went balls deep into her and just stayed inside her, without pumping. I could feel her pussy muscles tighten around my thickness, pulsing ever so slightly. Jessica lowered her legs and wrapped them around me. She pushed me into her and gyrated her hips. I let her do this for a little bit before I pushed back against her legs so that I could start pumping her. “Oh My God!” She cried out in pleasure. “Fuck me Anthony.” I need you to fuck me hard and fast!”I did as she commanded and I started pumping her hard. My balls slapped her ass as my hips slammed into her inner thighs. She propped her legs up onto my arms and I supported her thighs with my hands. I pounded her for several minutes as she moaned and screamed in ecstasy. “Don’t stop Anthony! I’m going to cum!” She cried out.I felt hot, wet fluid come stream out of Jessica’s pussy. It ran down my balls and thighs, to my feet. I was completely soaked. Seeing her cum like that took me over the edge and I felt myself reach climax. I pulled out of Jessica, grabbed her legs and spun her over, so that she was laying down on her stomach. I spread her ass and slipped the tip of my cock onto her hairy asshole.”What are you doing Anthony?” She asked, still trying to catch her breath from her powerful orgasm. I pressed the tip of my cock into her asshole, without penetrating her and I jerked myself off until I came. I filled her asshole with my hot cum and just as my orgasm subsided, I inserted myself back into her pussy and pumped her until I started going soft. I spread my cum around Jessica’s asshole with my left thumb while I fucked her and she squealed. She loved the sensation she felt as I massaged her well lubricated asshole.Jessica’s pussy muscles pushed my cock out of her after I went soft. I laid down on the bed, next to her. She rolled over to face me and we kissed for the first time. She slipped her tongue into my mouth and we made out for several minutes. “I need to call your mother and ask her if you can spend the entire summer with us.” She whispered.I laughed and kissed her some more. This was definitely going to be a summer I would never forget. Things were just getting started and there was a lot more to come.

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