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My Friend's Son

By: funallie24



My name is Lisa. I am 43 and have been married to Joe for almost 20 years. The past few years, Joe has been traveling a lot for work. We have been spending long periods away from each other and have definitely been less intimate. It was Thursday morning and he was getting ready to head off for a week in California. He woke up late and rushed out in a whirl wind, he was supposed to get up at 4 am to catch his plane. Unfortunately the alarm did not go off and he woke at 5:15. He ran through the house cursing, grabbing his things and racing off. I managed to fall back to sleep until 7:30.

As I was getting ready for work, I noticed he had forgotten his laptop on the table. Wow I thought he must have been frantic this morning, he never goes anywhere without his laptop. I picked it up to put in the bedroom. I must have touched a button because the screen opened up. It was on his hotmail account and he was still logged in. There was a chat box opened up with someone named Sexylady saying hello to him. I put the laptop down and took a glance through his old mail messages and found many from this Sexylady person who turned out to be a woman named Jenny.

This was how I discovered he is having an affair. At first I was hurt and shocked. I wanted to confront him and yell at him, but there was no way I could contact him. He would be on the plane for the next 4-5 hours. I was crushed, embarrassed and insulted, I wanted to throw him out of the house.

I was so upset I thought about calling out from work but decided I needed the distraction to think about what I should do.

When got to work, I called my best friend Dina. She is currently divorced and I needed to talk to someone for advice. She was outraged at Joe and insisted I come over to her house after work and stay with her for the weekend. I agreed.

After work I stopped at home and picked up a few things and drove to Dina's. She had a glass of wine ready when I got there. We drank the whole bottle. I told her everything. We cried together and discussed all my options. She asked, when was the last time you had sex? I really could not remember. It must have been 6-8 months ago. I felt so guilty. Had I driven him to cheat? The more I thought bout it the worse I felt. I confessed I had not given him a blow job in years.Dina was very comforting and assured me it wasn't my fault. I wasn't totally certain. I still loved Joe and deep down didn't want to leave him but I was also so hurt.Dina uncorked another bottle of wine and I cried some more. I was in no mood to go to work tomorrow. Dina convinced me to spend the day at her house. She has a beautiful pool and told me to make myself at home tomorrow. She had to work but would be home around 5.

She set me up in the spare room and went to bed. I stayed up a bit longer and finished the rest of the wine as I pondered my future.

and I am a I awoke at 10:30 with a small headache. I went down stairs and made coffee and scrambled eggs. Dina had left me a bathing suit and a note telling me to relax today and try to enjoy the pool. I cleaned up all the dishes, went to the spare room, changed into the bathing suit which looked ridiculous on me. Dina wears a 34B and I wear a 36C. My breasts were completely popping out of the top. and to make matters worse, she has a larger bottom than me so the bikini was so loose it was practically falling off. I looked in the mirror and laughed at myself. I straightened up the room and went out to the pool. I put on suntan lotion and sat down on a lounge chair.

I flipped through a magazines and read my book for awhile. It was getting really hot! I got up and dove into the pool. What a mistake, The bikini came right off I laughed to myself as I gathered the pieces and flipped them up to the lounge chair. I was nude but her backyard was completely isolated so I didn't worry. the water felt great, it was so refreshing. After awhile I got out of the pool and climbed on to the lounge chair to relax and enjoy the feeling of the suns rays on my nude body. I must have drifted off.

I must have been dreaming, I felt a wonderful tingling feeling across my body. I woke up and couldn't believe 3 hours had passed. I must have been exhausted with all my stress and crying. I sat up, the bathing suit was folded neatly on the chair. I didn't remember folding it, oh well I thought as I stood up. I didn't feel like putting it on, I was actually enjoying the free feeling of being nude. I walked over to the pool. I sat on the edge for awhile, then eventually jumped in for another swim. I was really enjoying myself and completely relaxing. After a nice long swim I got out and went to the lounge chair. I was horrified when the I saw a glass of lemonade on the table. I know that wasn't there before. I looked into the kitchen and saw Dina 's son James in the kitchen doing the dishes. I was so embarrassed. How long had he been home? I quickly grabbed the towel, put on the bathing suit and hid under the towel. I nervously sipped the lemonade. I

stayed outside until Dina came home.

When she motioned me to join her in the kitchen, I nervously looked around for James. He was not here. I felt so relieved. Dina asked how my day was. I told her It was great. I left out the part of her son seeing me nude in the pool. Dina popped open a bottle of wine as we made diner together. After awhile she mentioned that her son James was coming home later from college for the weekend. I neglected to tell her he was already home. I guess he hadn't told her either. I felt relieved of that.

She had made plans for us to go out to a bar in town to meet two of her girlfriends. After dinner, I went up to shower and get changed for our night out. I put on a sexy blouse and a pair of jeans.When I came down stirs,Dina and James were both waiting for me. Dina said, you remember my son James. He quickly smiled and said Hi Lisa and gave me a hug and kiss on the cheek. I was so embarrassed. I could only manage a weak , hello.

Dina explained that James was going to drop us off at the bar and pick us up later so we wouldn't have to worry about drinking and driving. We all got into the car and James drove us to the bar. I was very quiet in the car. We arrived around 8. The the girls were already there. We ordered up a few drinks. After my third drink,Dina began to ask me about Joe's affair. I was feeling a bit drunk and told the girls all about it. They were so mad at him. Christine told me that if her husband ever did that she would cut off his dick and leave him. Beth disagreed with her saying that she would get even by fucking one of his friends. She was trying to convince me to pick someone up tonight and screw them. Both women were pretty relentless with their advice. Eventually Dina said she agreed with Beth, I should get even with sex not dismemberment. We all laughed over it for awhile. Fortunately or unfortunately, Christine was the first one to leave. We were all getting pretty drunk and Dina and Beth kept bringing guys over to meet me. I have to admit I was loving the attention. I was feeling very sexy.

At around 2 am. Dina was wasted, she called James to pick us up. James arrived shortly. We all got in the car. He drove Beth home first then we headed home. James had to help his mom up to her room. I went to the kitchen to get a glass of water. I was feeling pretty drunk myself. I stood for a moment thinking about all the different guys that had hit on me tonight. Part of me wished I had been a little bad and at least gotten a number or something. Oh well I thought. I was about to go upstairs when James walked into the kitchen. He had a hungry look in his eyes. I nervously smiled at him and attempted to walk by him. He grabbed me by the waist and pulled me back into the kitchen, I was corned.

Before I could react he was kissing me. I was shocked stunned, he thrust his tongue into my mouth. I tried to fight him off , he held me tightly! I felt his hands slide up my blouse over my breasts. He managed to unhook my bra. I was stunned, a wave of pleasure raced through my body as he pinched my nipple, instinctively I let out a gasp. I suddenly realized what was happening, I tried to push him back, he resisted my weak attempt, as his other hand pushed down the front of my jeans. I tried to squeeze my knees closed but it was too late, he was rubbing my pussy through my panties! It felt so good,I instantly felt terribly guilty but I was actually getting wet and hot! He pinched my nipple again as he found his was under my panties, his tongue was swirling in my mouth. I felt his finger slide through the folds of my labia. I couldn't believe what was happening! He had two fingers sliding deep into my pussy and I was kissing him back now. I hadn't had sex in months and here was this 19 year old fingering my pussy. My god it felt amazing! I haven't been touched like that in almost 20 years!! Needless to say, I came within minutes!

He continued to kiss me passionately, I pulled back and looked into his hungry eyes, reached out touched his crotch, I felt his cock was rock hard through his jeans, I was not stopping now, I wanted that cock! I led him upstairs to the spare bedroom, pulled him into the room, closed the door and pushed him to the bed. I unzipped his pants and pulled them off along with his boxers. I ran my hands up his beautiful thighs to his balls and stiff cock, gently caressing them. He moaned with pleasure as I licked his balls and slowly stroked his cock. I ran my tongue slowly from his balls up his long shaft and kissed the tip of his cock. My lips were met with a flow of his salty precum. I took a long slow sensual lick, I could taste the sex! I squeeze his shaft tightly, desperately licking at the flow of precum . I haven't given head in years! I had forgotten how arousing taste of cum can be. I took his beautiful cock deep into my mouth, I sucked and licked his cock up and down. I was so wet and horny, he was moaning with delight as he thrust his cock deeper down my throat.

I had to have his cock inside me. After a long sensual session of head, I climbed on top and straddled him. I bit my lip as I eased his cock into me! I slowly rode his cock up and down. Suddenly he turned me over and entered me from behind, I was about to cum when I heard a noise in the hallway. Dina had gotten up to use the bathroom right next to us.

I stopped with fear. I could hear her in the next room! , James refused to stop he pounded in and out of my pussy faster. I bit the pillow as I came all over his hard cock! He continued fucking me, the bed squeaked loudly, He came hard deep inside me! Oh my god I thought, I just fucked my friends son! 

My Friend's Son



As told by cathy:

"Come on, Jane, it's not like I'm gonna hurt him!"

"Cathy, you can't be serious! I mean, what kind of mother would I be?"

I looked across the breakfast table at her, divorced for 12 years, an 18 year old son she dotes over. Both really nice people, but she's been sheltered, and now so has he. I said, "You're a concerned mother who wants what's best for her son. Nothing wrong with that."

"He's not just shy," she argued. "There's something else there! I wish he would meet the right girl and all this will be a thing of the past, but I don't think it will happen."

"Maybe," I replied, "if he is put in the right situation? He obviously has the desires, it's just a matter of channeling them."

Tim's father had abandoned them before I met her. Tim was six at the time, Jane was 27. Many years later she found out her ex had died in a bar fight in Denver.

I met Jane because my daughter sat for Jane. Lisa is ten years older than Tim, and he adored her. She was married now, living in LA, but Jane and I stayed close, and Tim was almost like a nephew to me.

When he turned 12, he had the normal teen reaction to girls, shy but curious. The accidental discoveries in his room told Jane he developed a collection of porn, including some of her undies that she thought she had lost. This worried her.

I tried to explain that this was fairly common among teens, that he was curious of females in general, and wasn't a perv because he liked to peek at Mom in her undies. Se just happened to be handy. 

Jane saw this as a sign of a deeper problem. Without a male influence in his life, she had no one to talk to him. And since I was her closest friend, she bounced these things off me.

I had become sort of like her big sister, since I was nine years older, at 48. Our personalities couldn't be more different. I'm out-going, strong-willed, self-assured, most times, and she's not.

I'm a full figured girl, 5'8, 150, with a 38DD chest that always turns heads, while Jane is 5'3, slight, not quite petite, and a 34B. We are both red heads, but she's a natural, I'm a Clairol Girl. Our choices in make up are just as drastic, as you can imagine. I never go out without it, and she barely wears any.

But, we have remained close friends, even now, and Jane knew that if she asked my opinion on something, I didn't hold back.

Tim was his mother's son, alright. At 5'9, and 140, I towered over him in my always-present heels. He was red-headed, freckled, sort of a Richie Cunningham-type, who was so shy around girls his age, but was right at home with Mom and me.

Now, to the problem: Where I took Tim to be a normal kid, with normal curiosities, Jane took his actions to mean he was a future cross-dresser, who would some day die on an operating table in Copenhagen in the middle of sex-change surgery!

She poured more coffee, thinking about my proposal. "You really think it would work?"

I shrugged. "Only one way to find out, and the worst that can happen is he realizes that you think there's a problem. That alone can open lines of communication."

"And, you have no problem with this?"

Another of our differences is Jane has pretty much given up on sex. I, on the other hand, would not even tell Jane of all my male friends for fear of shocking her. And among my favorites is younger men.

I reached across and touched her hand. "Honey, you know how I feel about you both. If I can do something so simple to help, I have no problem at all."

And so it was that we began to plan The Seduction! Over the next few weeks, I had to hide my excitement as we discussed plans, finally coming up with me needing help painting on the same weekend she was to visit her sister.

She would ask Tim to stay with me that weekend, to help me move things. During that weekend, I would make advances, using my unmistakable sexuality to seduce him and turn him from the Dark Side forever!

Through it all, I never mentioned how Tim would give me extra big hugs when she wasn't around, and occasionally brush up against me in the kitchen, and how I would feel his eyes taking in my 38DD's. This kid was no more gay or confused than I was. He was just shy with girls, and this may actually work! If nothing else, I would sample a fresh young cock.

Tim was just as happy not to be going to Aunt Mary's, and I had a big screen tv, with video hook-ups so he could play his x-box or whatever it was.

I picked him up Friday after school, Jane had him waiting like he was going to summer camp. "Do you have everything, Honey? You sure? An extra pair of boxers? PJ's?"

Tim blushed, rolling his eyes at me as we loaded up. She gave him a big hug like he was going off to war, and he sheepishly climbed into my SUV. "Bye, Honey, love you! Be good, okay? You listen to Cathy!"

I started the car. "You ready to go?"

He smiled, "Get me away from this crazy lady!"

We both laughed, and I'm sure Jane wondered what the joke was.

It was dark by now, no sense to start any projects. We picked up a pizza for dinner. Since he's 18 now, Jane lets him have a beer or two, and I knew he wasn't going out, so I had a 12 pack at home, along with my wine.

The baseball game was almost over, but we watched the end while we ate, with Tim being his normal self (for when she's not around!)and he downed 3 beers quickly with the slices, talking busily about school, sports, anything but his Mom. It was apparent that he loved her, but the pressure was building, even if he didn't know why.

A girl came on TV and I mentioned, "She looks something like my Lisa, huh?"

He glanced up. "Nah, Lisa's much prettier." There was that old crush coming out. 

"Any girls in school as pretty as Lisa?"

"A couple aren't bad, but not like Lisa! She's awesome!"

This had segued smoothly. "Have you asked any of them out?"

He shook his head, staring at the TV.

"Don't you like them?"

"It's not that, they're... they all like other guys, bigger guys, more cool guys."

"But, you're cool, right?"

He smiled at me, sympathetically, as one would a child who didn't understand the big picture. "It's different... I get around them and my mind shuts down, I can't think of anything to say, or my mouth won't work, so I come across as a dork."

"So, you just quit trying?"

"For now... maybe I'll have a growth spurt."

"Wait, this is all because of your height? I don't think so. If you use that to hide behind, you'll find another excuse when this one changes."

"You think so?"

"I know so, I've had male friends who were shorter than you, by a lot! And believe me, sideways, we're all the same height!" I laughed.

He was stunned at first, then got my meaning and turned red.

"You never heard that expression? Oh, that's right, I forgot who your mother is!"

He laughed at that, then said, "You're serious? You dated guys my height?"

"Sure, in fact, when you were older, your mom's gonna be very mad at me when I snatch you away!"

He smiled. "Yeah, I wish!"

I had to smile at how well this was going! "You wish? Wishes come true sometimes, you know? What exactly do you wish for?"

He looked away again. "You don't want to know."

"Oh, yes I do!"

"You'll just get mad."

"I promise, I won't."

He turned to me again on the couch, only a foot between us, and stared, deciding. "You promise? And you won't tell Mom?" I Nodded. "Okay, my wish... I wish... I wish that we could have sex! There!" and he clammed up.

"We, meaning you and me?"

He seemed braced for an attack. Hiding behind his shoulder as defense, he nodded, watching me.

"Okay."

"Okay? Okay, what?"

I stood up. "I just need to know, have you ever done this before."

He sat, looking up at me. "That's it? Okay? That's all it takes?"

"Timmy Honey, that's all it takes from me. As far as other girls, they may want dinner and a movie, and maybe you shouldn't be so blunt, but that's basically it!"

"Oh, so this was just a lesson, then. To show me what to do," his eyes accusing me for tricking him.

"In a way, it's the beginning of the lesson, and if you want to continue, I won't stop in the middle to explain things, we'll just let them happen." 

"I don't believe this."

"I was hoping to do this as a 18th birthday gift, and I'm only a month late. I couldn't offer in front of Mom!"

"Oh shit! I been... I mean, since i was 13, I thought about you, how you hug me, and how you gave me big kisses on holidays!"

I held out my hand and he took it and stood. I was much taller in heels, so I stepped out. Now we were identical in height. "Is that better?"

He nodded and I said, "If you don't like something, or it makes you uneasy in any way, and we'll work it out, okay?"

He nodded again, and I said, "Kissing okay?" and he licked his lips and nodded and I tilted my head as my arms slid around his neck. I could taste the beer as my lips parted and his tongue shot out! He had made out before, at least! 

We held the kiss, letting it sink in, nicely, letting him relax if that was possible but judging from his belly moving against mine, he wasn't about to relax.

I broke the kiss and stepped back, staring at him as I unbuttoned my black blouse, and watched his eyes fill with excitement. When I pulled it apart and let it fall, I took his hand and placed it on my breast. His hand closed, kneading my fleshy boob and I moaned. I was really getting excited by this.

I kissed him again, and his other hand followed the first, taking a tit, and squeezing. He seemed turned on by my reaction, and I slid the strap down and released the first tit, and he oohed when my nipple became exposed and hardened in the cool air. I unhooked the bra nad it fell, and I took his hand. "Let's go inside." 

My king-sized bed was covered with pillows of different sizes, and I tossed a few, then sat. He stood before me and I unhooked his jeans, seeing how hard he was, his outline pressed against the material. I thought of his mother making sure he had fresh drawers, and though of the stains these would have before the weekend was over.

His pants were down with the boxers and this tiny young man was sporting a good eight inches of pink-headed flesh, rock hard, and thick. What a pleasant surprise! I made a mental note to tell him the girls would love that, no matter what his height.

I tugged his hips closer and his cock twitched as I went to touch it, to kiss it, and I realized Tim was about to cum!

I wrapped my hand around it and opened my mouth just as he shot a stream of cum that seemed to hang in the air before hitting my cheek. I adjusted and he let loose again, this time, I caught it with my lips and tongue, then again, shorter and faster, he shot, and I was rubbing his cock all over my face, smearing his cum like moisturizer. He was panting, holding my shoulders for support as he waivered, then he moved next to me and slid to the bed.

"Oh, Cathy! Fuck! I didn't mean too ....you know, I'm sorry!"

I grabbed some Kleenex and wiped my mouth and face. "It's alright, Timmy, it's flattering that I could get you that aroused so quickly. You have plenty of time to learn to hold it."

"That's not it?"

I smiled. "Not by a long shot, Baby. We got all weekend, in between painting this place! Your mother would be curious if we don't."

He was panting as I stood and undid my slacks and pushed them down with my panties. His eyes widened when he got the full view, and he really liked that I shaved down there. I climbed on the big mattress and saw his cock begin to stir. I laid next to him and, in 69, I took his cock into my wet mouth, and hmmm, he tasted so fresh, so new, as I cleaned his cum off, swallowing. 

I felt his hands spreading me and he dipped into my hole, arousing me much more than he should have. My juices were flowing now and in a minute he was fully hard. I climbed on him, facing him, and held his eight incher to my throbbing clit and teased myself as with a dildo. i finally slipped the head past my lips and he groaned this time as he went further with each slow thrust. His eyes were wide when I could look at him, and I'm sure he was stunned at all this. His hips jerked erratically as I calmed him and set up a slow draw and thrust, feeling him moan with delight. I myself felt a groan pass my lips as he responded with deeper plunges. He felt so snug inside me, and I knew this had been a good idea.

I leaned down to kiss him, and he held my boobs, kneading them as he fucked me. His slams were faster, harder, making me feel waves of excitement. 

One more hard thrust, and he lined another stream deep inside me. Then another. We slumped together, exhausted. Finally, to break the silence, I said, "So, I hope you don't regret this."

He was smiling broadly when i looked at him. "Cathy, this is the best birthday ever! Too bad I can't tell Mom!"

"No, that wouldn't be a good idea, even if she asks some weird questions about your stay with me."

"Oh? You think she will? She doesn't seem to notice anything about... you know, sex. she wouldn't think that... that we... oh, shit! This was all a set-up?"

"Not like you think. Your mom was concerned." I told him about her undies,and his porn, and how she was worried, leaving off how she thought he might be a future Trannie. And I held him as we talked. "But, this was all my idea, honey, you have to belive that. In some cultures, young men are taught by an older, experienced woman from the Tribe. And I got all this pleasure from it too!. If you are angry with anyone, let it be me. I'll just tell your mom I chickened out. She will never know."

He laid there, against my breast, thinking. This had to be hard for him to comprehend, and I felt badly that I had deceived them both for my personal pleasure. I felt him breathing, and said, "Honey? Are you alright?"

He nodded, then said, "So, Mom knew we were gonna do this and all she was worried about was clean underwear?" and he laughed.

I smiled. "Yeah, Mom's do strange things when they are nervous about their kids."

He looked at me again. "Don't give her any details, just tell her I did okay. Okay?"

"You're the man, if that's what you want, that's what you get."

"And do we get to do this again?"

I smiled again, and said, "Like I said, Sweetie, your choice! But anything beyond the first one is pure pleasure. Nobody's business but ours!" Our lips met through the smiles, and our tongues began to play.