Mom, You're The Best

It all began with a drunken night out with my best friend, Helen. It was late and I could see she had something on her mind as she sipped her wine. "What's up?" I asked.

"Nothing," she replied.

"We've known each other since school, so I think I know when something's wrong."

"Christ, Jen, do you realize we have been friends for more than thirty years now?"

"Don't avoid the question, Hel. What's up?"

"That's the problem," she replied and paused. "Nothing's 'up' if you get what I mean."

"Oh," was my automatic response.

"I do love Fred, but he can't keep up with me. I think he's hit the age where he's more interested in golf."

I laughed then noticed the serious look on her face. "Sorry," I said and composed myself. "You knew this day would come. He is twenty years older than you."

"Yeah, I know, but..." She paused and I eagerly waited. "I didn't know he would lose interest just as I hit my sexual peak."

Helen held her wine to her mouth but didn't drink.

"I've decided I don't want an affair, but I do want more sex," she said, as she leaned closer to me and whispered, "I'm going to find me a young boy-toy."

"Wow," I said, without thinking. "Got anyone in mind?"

Helen frowned. "No," she stated, "The idea of picking up a stranger in a bar... I can't do that"

"The gym?"

She sighed. "I wish. Bit too close to home, if you know what I mean."

"No, you don't want a reputation," I replied and sipped my wine as a thought entered my head. Over the years we had shared many sex stories and I knew Helen was a highly sexed woman. She drank her wine I could see she was serious. "What about John?"

"John?" She replied, slightly puzzled.

"He's back from university. He's a fit young man. I'm sure he'd be willing."

"Your John?" She asked wide-eyed, staring at me. "Your son, John?"

"Why not?" I asked, not believing I was actually trying to set up my son with my best friend. I took a second to look at Helen and thought she would definitely be most men's idea of a MILF. Petite, pretty face, nice hair, good body, and a few laughter lines.

"Jesus, Jen, are you sure? I mean... he's your son. You wouldn't mind me fucking him?"

I laughed out loud, hearing her put it so bluntly. I was feeling slightly drunk and an image of them having sex flashed through my mind.

"He's twenty-one," I casually replied. "He's old enough to decide what he wants. But no, it wouldn't bother me." Helen looked away and I could tell she liked the idea. Then I felt a warmth between my legs. "In fact," I said, maintaining my composure. "It would be good for you both."

"Are you serious, or is this one of your wind-ups?" She asked, looking at me with a mixture of shock and excitement on her face.

"Helen, I... I wouldn't joke about you having sex with my son."

"You wouldn't mind me seducing your little boy?" She said, teasing.

"Go for it," I replied, trying to remain calm.

Helen laughed, then looked me in the eye. "You wouldn't mind me sucking his cock?"

"I think he'd like it," I said and we both laughed.

"Do you think he'd like to bury his head between my legs?"

"Not if you've got a wild forest growing down there," I said, pointing to her crotch.

"Smooth as the day I was born," she stated proudly, then burst into laughter.

I've never thought of Helen sexually, but I suddenly pictured her naked pussy and felt a hot flush run through me.

"Oh, Jen, you're getting me hot and flustered. You sure you wouldn't mind me having 'hot sex' with your little boy?"

"He's not so little," was my retort and Helen almost choked on her wine. That caused me to laugh at my choice of words. "I meant he's a good bit taller than you," I managed to say, taking a sip of my wine to hide my blushes.

Helen tried to compose herself. "I thought you meant his cock," she said and erupted with laughter. It was infectious and I laughed with her.

"Oh, Jen, you do make me laugh."

"What if I told you I'm not joking?" I replied with a straight face.

"Wow!" She stated. "If you're okay with it, then yes, John would be perfect, but..." She looked away and gasped. "Oh I don't know, Jen. It's not like I could pick him up in a bar. How could I..." she broke off and looked away.

The warmth between my legs was getting hotter and I was surprised at my reaction. "I'll find out if he's interested. I can't think why he wouldn't be."

"Thank you, Jen. That would be so wonderful of you." Helen giggled and leaned in close. "I feel like I'm back in school. Do you remember when I asked you to find out if Tony Jackson was interested in me? That's how I'm feeling now."

We chatted about her past loves and how I had married my first love. I don't have a high sex drive and I'm happy to let my husband, Ben, get what he needs.

Helen is a different animal and had had many lovers before she met Ben. He was an older man who knew how to treat a lady. To use Helen's words: "He knows how to both make love to me and how to fuck me. He's much better than any of those 'boys' I've been with."

I woke the following morning with a mild hangover and checked my phone. A message from Helen: "Thanks for a great night. If you are OK with it, set it up."

Later that evening while we were having a family meal at the dinner table, I took a moment to look at John. He isn't particularly handsome, but he's an attractive young man with youth on his side. His sister, Zoe, two years his junior, is beautiful with long blond hair and legs up to her armpits.

When we finished the meal John helped me with the dishes. As he loaded the dishwasher I composed myself and asked with a quiet curiosity: "What do you make of Helen?"

He glanced at me. "What d' you mean? I've always liked Helen, she's fun."

"She said something about being called a, oh what was it," I paused, feigning ignorance. "A... a Milf, that's it. Is she one?"

John blushed. "I, uh..., I don't think I should answer that." He managed to reply.

"Why not?" I asked, knowing full well why not. "What is a milf anyway?"

"Uh, I think you need to look that one up yourself," he commented and started the dishwasher. He left the kitchen before I had my phone out. I know what a milf is, but wanted to continue my little act.

An hour later both John and Zoe were in their bedrooms and Ben was in the living room. I figured if John had been masturbating then an hour would have been long enough and knocked on his door. A moment later he told me to 'come' which put a smile on my face as I entered his room.

He was on his bed watching something on his laptop as I sat down on the edge of his bed. "What's up, Mom?" He asked cheerfully.

"I looked up milf," I said and looked at him as he blushed.

"Oh," was all he could say.

"So, would you say Helen is a milf?"

"I... Uh... Why are you asking me?" He asked as he pushed his laptop away.

"Well. She told me she was a little surprised when she heard it and wondered if it was true. You're the only young man we know, so I said I'd ask you."

"Mom, that's making me a little uncomfortable. You know, you're asking me if I want to, uh, you know, with Helen."

I knew I had to make him relax. "It's nothing to feel uncomfortable with, Hon, you're a grown man now and we can talk like adults. If that's okay with you?" I asked, knowing he couldn't refuse a bit of flattery.

"Sure, no problem," he replied, a little flustered.

I felt my heart racing and glanced nonchalantly at his groin. "I'm going to say something now that you don't have to answer if you don't want to. If you want, we'll pretend this conversation never happened."

"Okay," he said slowly.

"Helen wants... she wants to know if... she wants to know if you would like to have sex with her? There, I've said it now, so would you?" I felt relief at managing to ask such a question and excitement at the same time.

"She wants to know if..." he trailed off, looking a little shocked.

I realized the 'if' part didn't complete what I hoped for. "If you want to, she would like to have sex with you. Just two adults having a bit of fun. Not an affair or anything like that. It's just sex."

"Jeez, Mom, I, uh, I wasn't expecting that." He said and took a deep breath as he looked away. "But what about... What about Fred?"

His consideration made me smile and think he is a decent young man. The fact he didn't say no also encouraged me. "Let's just say he's quite a bit older than she is, do you understand?"

"Oh, right," he said quietly.

"You'd actually be doing him a favour and she'd stop nagging him." I watched him think and knew he was interested. "She has got a good body, and between you and me, I know she has a dirty mind."

"Really?" He enquired, as he sat up against the headboard.

"You wouldn't believe some of the things she has told me." Out of the corner of my eye something moved and I briefly glanced at his crotch. "That's an impressive bulge," I thought, just before he covered his semi.

"Uh, wouldn't you think it a bit weird?" He asked.

I smiled at him. "My best friend and my son making her happy, that would make me happy. So if you want to, you can."

"This is crazy, but good crazy," he stated, as he tried to think. "What about the how and where? I mean, we would have to be discrete."

I put my hand on his thigh reassuringly. "In a couple of weeks your father and I are taking Zoe upstate for an athletics meet. You'd have the house to yourself for the weekend. Would that work?"

"Fuck, yeah." He said excitedly. "Sorry, Mom, I didn't mean to swear like that."

"That's alright, Hon. If I was in your position, I think I'd swear a bit too." He moved his hand from his crotch and stroked the back of his neck. I couldn't help but look at his tented jeans and I was impressed.

"I take it that means yes," I said, gesturing to his cock as I rose from the bed and made for the door. "Shall I tell her yes and to make the next weekend free?"

"Uh, yeah," he answered, still shocked. "That would be great. Thanks, Mom, you're the best."

He watched her leave his room, then thoughts flooded his head: "What the fuck just happened? I'm gonna fuck Helen. Mom set me up with Helen. Jeez, she's been my fantasy since I was... thirteen. How many times have I thought of her when...? She wants to have sex with me. Mom set it up. She wants me to fuck Helen. She looked at my cock. Don't go there. I can't believe this, I'm gonna fuck Helen."

I left his room and briefly wondered if he would be masturbating as soon as I left. I felt strangely aroused that I had set my son up with my best friend. I ignored the thought of him masturbating, but the size of his bulge did make me stop and feel the heat between my legs.

The next week flew by with John asking me several times if Helen was still coming around on Friday. With a wicked smile I told him: "She'll be coming, alright." The startled look on his face was a joy to behold.

Friday evening and Helen drove over to Jen's house. She parked outside and was relieved to see Jen's car wasn't there. "Now or never," she said to herself and took a deep breath. Her heart was pounding and she could feel her nipples pushing against her bra. She grabbed her hold-all and got out of the car as John opened the front door.

"Hi, Helen."

She looked at him thinking: "This is going to be fun. Let's teach him a thing or two."

"Hi, John. I'm glad you don't mind me coming over."

"No. No, not at all," he said, slightly flustered as he welcomed her into the house. "Would you like a glass of wine?"

"Great idea," she replied and followed him into the kitchen.

As John uncorked the bottle his mind was a whir: "She's fucking gorgeous. Am I really going to fuck her? Jeez, don't get a boner in front of her. Be smooth."

"Jen told me you've just finished at uni."

"Yeah." He replied, taking a seat facing her on the opposite side of the kitchen table. "Still trying to find a graduate training job. No luck yet."

As the wine flowed and conversation continued about possible careers, Helen realized she had to take the initiative. "John, are you okay with what I want?" She said, looking him in the eye.

"Uh, yeah," he tentatively replied.

Helen mistook his nervousness as reticence. "You don't have to do this if you don't want to."

"No. I, uh, I mean yes. I do want to," he spluttered.

Helen got up and approached him. "I'm more than twice your age, John, and I'm not as pretty as the girls your age."

John tried to think of something to say, but his mind wasn't functioning properly. Helen suddenly felt nervous. "If you don't want to, I understand. We'll just pretend this never happened."

"No. No. I do want to. It's just I..." he blurted out. "I've always wanted to... with you... uh..."

She felt invigorated by those words and felt a shot of adrenalin shoot through her body.

"It's alright to be a bit nervous and you'll get over that quickly. Now here's what's going to happen," she said as she stroked his cheek. "You being young I don't want you to worry about cuming too quickly." She looked at him and saw the look of surprise on his face. "In fact, I'll get you to cum quickly, then we can relax and have a great weekend having sex. Would you like that?"

John couldn't believe his fantasy was going to be a reality. "Yeah," he said croakily.

"Good," she replied and smiled at him. "I'm just going to go upstairs and get changed. You wait here."

The next ten minutes were the longest ten minutes of his life. Then he heard her on the stairs. His jaw dropped as she entered the kitchen wearing a black and red lacy Basque, black panties and nylons, and black high heels.

Helen saw his reaction and strode confidently into the kitchen and stood in front of him with her hands on her hips. "See anything you like?" John could only nod as he looked her over. He gasped out loud as she raised a leg and placed her stiletto clad foot on his crotch and pushed against his cock. He gazed between her thighs at her panty covered pussy and breathed in deeply.

"That feels like you have something I'm going to like. Strip!" She said and turned away, walking the length of the kitchen wiggling her hips.

John leapt to his feet and pulled his shirt over his head as he watched the sexy woman walk. He kicked off his shoes and pulled off his socks and jeans as he watched her return.

"And the boxers," Helen commanded. A second later and John was standing naked in the kitchen with his cock as hard as it had ever been, looking at the sexiest lady he had ever seen in real life.

"You look fucking hot," he said lustfully.

"And you have a nice cock," she replied, leaning down to get a closer look. "Not too long, but nice and thick. Wow, that is thick." John gasped as she took hold of his cock. "Look at that. I can't get my hand round it," she said and let go of him. "Where would you like to cum first?" She asked seductively. "In my mouth?" She asked and licked her lips. "On my tits? In my pussy? Or in my ass?"

John was stunned at how raunchily she sounded. "In your..."

"Stop! I'll decide. I don't want you soaking this Basque. Not yet anyway." She stated, then strutted around the kitchen.

John could only watch and was amazed by how sexy her legs looked. He wanted to grab his cock, but resisted the urge as she approached him.

"Get down on your knees," she commanded and he complied. "No hands. Lean forward and smell my pussy."

John leaned forward, his nose an inch from her pussy and breathed in deeply. Her musky scent caused his cock to throb.

"Now take off my panties," she instructed.

He moved each hand to her sides and slowly pulled the lacy panties down her legs. He marvelled at her smoothly shaved pussy and the delicate little slit between her legs. "Fuck me," he said in awe of the sight before him.

"Not yet, but soon." She replied and raised a foot onto his chair. "Now lick my pussy." She looked down as John's tongue snaked out of his mouth and she felt him slowly and gently lick up one side of her pussy and then the other.

She was impressed he didn't race straight to her clit and a few licks later her body quivered and she pushed her pussy onto his face. "Oh, that feels good," she said huskily. "Keep doing that."

John bent down a bit further and licked the length of her slit, gently pushing his tongue between her lips. The scent and taste of her pussy was driving him wild and he instinctively took hold of his cock.

"If you want to enjoy my pussy, you better let go of your cock." Helen stated sternly.

"Sorry," John replied, then stroked his hand up the length of her thigh and over pussy. She was hot and getting wet. He slid his index finger into her pussy and slowly stroked the inside of her moist hole.

Helen took a sharp intake of breath and felt her heart race. She felt his finger on her G-spot and her body reacted with a spasm. Then she watched him cup the top of her pussy with his mouth and lick her clit, as his finger worked magic.

"Suck my clit and finger my pussy. Oh, God, that feels good." She moaned as she felt her orgasm build.

John lapped at her clit then drew away and blew a stream of warm air on her pussy. Her body flinched slightly, he was pleased he was turning her on. He slipped another finger inside her pussy and pulled her towards him. Her pussy squelched and he fingered her vigorously, revelling in the sight, smell, and the sounds coming from her pussy.

The noises coming from her pussy turned her on and she knew her orgasm would be soon. "Make me cum, John. Do it. Make me cum. Ah, that feels good."

John looked up at Helen and smiled as he worked his fingers inside her pussy and massaged her clit with his thumb. "Cum for me, Helen. Cum for me," he said as she threw her head backwards and moaned out loud.

He continued working his fingers and felt her pussy contract and spasm. Then Helen let out a little squeak and her body shuddered. She flinched again and a small squirt of her juices splashed into the palm of his hand.

"Wow!" He exclaimed, having only ever seen a squirter in porn. He slowly licked his palm.

Helen looked down and watched him lick her juices. "Oh good," she thought, "he's up for some kinkiness. That was much better than I expected."

John stood up and faced her. "Did you like that?"

"That was a good start, John," she replied. "Now it's my turn."

He watched as she knelt down and admired his hard cock. She stroked his cock with her right hand and pre-come seeped out over his crown. The sight of the fluid triggered her response and she licked his crown and felt his cock throb in her hand. She rubbed his cock over her cheek and looked up at him. "Sorry, but I can't fit this in my mouth."

"Use your tongue and suck as much as you can," he said, feeling his body heat rising and his heart pounding.

Helen looked at the marvellous cock and licked his balls, then licked the length of his shaft and sucked his crown between her lips as she gently stroked his cock. She felt his legs twitch and knew he would cum quickly.

John watched as Helen sucked his crown and stroked his cock. When she looked up at him and swirled her tongue over his crown, he felt his semen build.

"Fuck, that feels good," he blurted out.

Helen grabbed hold of his cock with both hands and rapidly jerked him off inches from her face. She felt his cock spasm and looked up as his first jet of cum exploded from his cock over the top of her head.

John gasped when his orgasm shot into the air, then felt her warm luscious lips engulf his cock-head and the next stream of sperm erupted into her mouth.

"Oh, fuck, yes," he exclaimed and pumped his semen into her mouth.

Helen was surprised of the amount of semen she swallowed and felt his legs buckle. She released his cock and he stumbled back against the table.

"That was fucking amazing," he said, breathing heavily as Helen stood up.