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It was actually Jeff who brought the subject up, a few weeks after Ed’s 18th birthday. Lying in bed, post coitus, his hand still touching her small brown breast, Jeff began.
“You know, we’ve done a pretty great job raising Ed, I’d say. Most of the credit is yours, for sure. He’s technically a man now, and you’ve been the best mom in the world. We never held anything back. We were always honest. I think he learned a lot from us that he’ll need to get along in life. Stuff about people and social situations that lots of kids struggle with. Not Ed, though. He’s so well adjusted that it’s scary.
“So, now I’m wondering if you’ll do what you said you would all those years ago. I mean, get him a tutor for his first real sexual experience. Or is that just a step too far? Should we just let him find that experience on his own?”
“Actually, it’s been on my radar,” said Emily. “I was so stupid about sex when I was his age, and my first experiences were a disaster. I’m lucky that I didn’t turn off to sex completely. My parents were so strict and silent on the subject, and I didn’t have a clue. I won’t let that happen to Ed.”
“Do you have someone in mind, then?”
“Yeah. I’ve been talking to Maeve about it,” she replied.
“Maeve Swan? Holy cow, she could kill him! Don’t you think you should start with somebody a bit more tame? Like maybe Wonder Woman?”
Emily knew well that Jeff considered her friend Maeve to be one of the sexiest women around. She had long red hair, the whitest skin, great curves, and boobs like firm melons. Men, including Jeff, were known to gasp and wipe away drool when she walked by. But to Emily, she was just a dear friend. One to whom she would trust her only son. One who would know how to guide a young man through his first sexual experience with kindness and skill.
“Lord knows,” she thought, “Maeve certainly has the qualities and experience to make a young man like Ed feel good about himself, and sex.”
“Maeve will be great. She’ll be gentle and show him all he needs to know to become a good lover. I trust Maeve. She’s really my best friend.”
Jeff said, “Well, I just hope our boy has a strong constitution. Maybe we’d better get his heart a checkup before you throw him in with the Lioness. When is all this happening?”
“Oddly enough, I’ve got a meeting set up this Monday evening to work things out. Just Ed, Maeve and me, at The Green Frog.”
At 6:30 Monday evening, the three of them were sitting at a patio table outside The Green Frog. No other customers were outside, which was as Emily expected. She wanted this talk to be private, for obvious reasons.
Emily began, after they’d finished dinner. “Ed, you know your dad and I have always tried to be honest with you and give you the tools and education you’ll need when you’re out on your own. We’ve never shied away from the subject of sex, or any other topic. You’ve always been honest with us, too, I hope.
“I know you’ve dated some, and you volunteered that you’ve made out with a couple of girls. But you haven’t actually had sex with any. Is that correct?”
Ed smiled. “Yeah, that’s about right, Mom.”
“Well, now that you’re officially a man, your dad and I would like to offer you the opportunity to have your first complete sexual experience with a woman. We do this because we’d like for you to be introduced to full sex by a person who can teach you things and give you a positive experience. You know, I’ve always felt that my first experiences with sex were a disaster, and we’d like to save you from that fate. When you meet someone special, you’ll have the confidence and skill to be a good lover, which will be extremely important to your future relationships. Is that something that…interests you?”
“Sure. It looks like you’ve got this all planned out. You wanna let me in on the plan?”
“Ed, the reason Maeve is here is because she’s agreed to be your first. This means that your dad and I trust Maeve to guide you through what should be an extremely pleasurable experience, and you should come out of it with confidence and pleasant memories to last a lifetime. If you agree, then next Saturday night you’ll spend with her, at her house. What do you say?”
Emily looked at her son with a big smile of expectation. Maeve smiled her best mentor smile, pushing her large breasts out just perceptibly.
Ed answered slowly. “Nice offer, Mom. Maeve, you are so beautiful. I know you’d be a great teacher. But I’m gonna pass. Thanks anyway.”
Emily was sure she hadn’t heard correctly.
“Wha…Did you understand what I said, Ed? Maeve has agreed to have sex with you and teach you, and…I can’t believe you’d turn that down! You don’t have to be afraid of Maeve, Baby.”
“Well, Mom, you know, I should have some say about who I sleep with. Doncha think? I appreciate what Maeve is offering. Maeve, I love you and thank you for being so kind. It’s just not what I want. My first should be my choice.”
Ed started to get up from the fake taxi porno table. His mom tried to salvage the situation.
“Honey, don’t leave. Let’s talk about this. What exactly do you want? You wanna have your first sex in the back seat of a Chevy with some drunk high school girl? That’s not the way. You need someone with experience, who loves you.”
Ed sat back down and looked from one to the other. Then, very pointedly and in a low voice, he said, “That’s right, Mom. If I had my choice, I’d choose someone who loves me and someone with experience. I’d choose you, Mom.”
Emily, whose mouth was hanging open, closed it and gulped. “What the fuck have I done? What in hell gave him that idea?” She stared in disbelief as Ed rose, turned, and left the restaurant.
“Okay, what just happened? I offered a teenaged boy the sexual opportunity of a lifetime, one that no grown man would turn down. No straight one, anyway. And he turned it down!”
For half an hour, the two women discussed the evening’s shocker. Finally, Emily asked her friend, “So, what do I do now?”
Maeve, looking at the table, slowly said, “Well, Honey, you could, you know, do what he wants. You could be his teacher. It’s only for one night, and you’ve been his teacher for all his other life lessons. Maybe it’s the right thing to do for him?”
“You’re joking, right? Even if I thought it was a good idea, what would I do about Jeff? He’d never agree to that. He’d likely divorce me.”
“How many years have you been married? Don’t you know by now that you can more easily get forgiveness than permission? Don’t tell Jeff.”
“Well, I think he might just figure it out if I’m gone overnight! No way to hide that from him. All he’ll have to do is look at the empty spot where I usually sleep, and even a man can figure that one out.”
“Fill that empty spot.”
“You bring Ed to my house and I go to yours, as soon as things are underway. I’m pretty sure, after seeing Jeff ogle my bod for years, that he’ll take us up on the offer. I’m pretty sure I can take his mind off you and Ed for a night. Think of it as tit…for that,” she said, pointing in the direction Ed had gone.
Emily was silent. She was far from accepting the idea, but she wasn’t rejecting it outright.
By Tuesday, Emily was actually considering the idea. On Wednesday, she was leaning in that direction. By Friday morning, Emily, Maeve, and Ed were all on board, and there was an overnight bag in Emily’s trunk. The plan was for Mom to drive with Ed to Maeve’s. Maeve would leave and take her time driving back to Emily’s, ensuring that things would be beyond the point of no return.
It’s Saturday night. With her two guests getting warmed up at her house, Maeve walks into her friend’s house and encounters Jeff, sitting on the couch. She’s wearing a full skirt that accents her hips and a flouncy blouse, open to the point where her white cantaloupes bulge out with the aid of a special black bra.
“Jeff, there’s been a change of plans.”
Jeff rises and says, “What’s up? Where’re Emily and Ed?”
“They’re at my house. Jeff, when it came down to it, Ed wouldn’t go through with the plan. He…wanted a different tutor…he…he wanted Emily to teach him.”
“He WHAT??? I’ve gotta stop…” Jeff moves to cross the room toward the front door, but Maeve cuts him off, clutching his arm with that white hand of hers, and rubbing those pale globes against his chest.”
“Jeff, it’s too late. They’ve already started. Emily is so sorry, Jeff. That’s why she sent me, to be with you tonight. Jeff, I’ll stay with you tonight and keep them off your mind. Jeffrey, you can have me tonight.”
She pulls one side of her white blouse to the left, so he can see her boobs in the squeeze of the black bra. Her skin is almost as white as the blouse, and the contrast with the black bra is striking. Maeve reaches up and pulls Jeff’s mouth to hers, and she guides his hand to her cleavage. He’s hooked.
In the dim bedroom now, she removes his outer clothes and seats him on the marriage bed. The place where only he and Emily have had sex. Maeve steps back and begins an agonizing strip, turning slowly as she removes her heels, her blouse, her skirt. She has on black stockings and a garter belt, topped by the black push-up bra. Sometimes you can’t beat the classics, especially when they contrast so effectively with that wonderful pallid skin and long red hair. Jeff’s boxers are notably lumpy, and his eyes follow her every curve. What the hell!
He keeps saying to himself, “Emily is giving me permission. I don’t feel guilty. God, is she hot!”
Before now, having sex with Maeve had only been a fantasy, enjoyed in his mind while his body humped his wife.
She approaches the bed and tells him to lie down. She pulls Jeff’s drawers off and crawls up, straddling his feet. Jeff, looking down at her, realizes for the first time that she is not wearing panties family stroke porno under the garter belt. Her trimmed sex hair is a darker shade of red than that on her head.
With a smile at him, Maeve leans over to take his cock head into her red lips. She’s very gentle. He’s plenty aroused, and she doesn’t want him exploding right away. The oral action is perfunctory and given to him only so he will understand to expect more of it later, when he may need the extra stimulation.
Maeve is not fucking Jeff strictly to help her friend or to give pleasure to him. She wants her own satisfaction, too, and she’s learned over the years to always ensure her climax first. That’s why she’s taken control and put him on his back.
Now, she scoots up the bed and puts his cock into her damp hole, after sliding it around in her juices first. She eases it in, despite his reflexive push upward. Then, his eyes fixed on her, the only sounds in the room being heavy breathing, ooohs and ahhhs, she does the big reveal.
Those boobs! So long admired from a distance. So different from Emily’s. She reaches behind to unsnap the bra clasp, and they gradually come into view. She drags the moment out, and she feels a cock lurch inside her when they are fully on display. So heavy, but firm looking. Big, but not flopping around huge. White, with small pink nipples and areolae. Just so perfect.
He reflexively reaches for them, and she squeezes her upper arms in to accent their perfection. As hands glide and feel, Maeve bends to put her packages right in his face. He latches onto a nipple like a baby. Those boobs in his face are almost as great as his cock in her pussy, but not quite.
Maeve sits back up and concentrates on her own pleasure now. As she rolls her hips, her middle finger diddles her clit. Who knows what she’s thinking about as her head rolls back, eyes closed? Frankly, Jeff doesn’t care. He’s enjoying the feelings and the show. Never was porn this good.
Jeff has learned plenty about sex in his years with Emily. He’s been a good lover, which in many cases simply means considering his woman’s needs first. He wants Maeve to get off, because he knows she’ll be more into his pleasure when she’s had her initial satisfaction.
She’s not having to work hard to get to her climax, and now she rocks forward and backward as she masturbates, breasts keeping time like two pendulums. Jeff, who can usually hold out a long time when he’s on his back like this, is being carried along by her impending climax to one of his own. As Maeve hits her peak, Jeff’s hips are ramming up into her, his hands on her waist, his juice blasting into her hungry maw. In desperation to keep the climax going, he flips her onto her back and finishes with hard strokes of his cock, while her stockinged legs wrap around his back. They finish, spent. Slowly they roll to the side, Jeff’s tired cock dragging cum across her stockings.
Maeve laughs. “Jeffrey, you’re awesome! Let’s get married, okay?” she teases.
“You’re a bit too late. Remember your best friend Emily? I’m kinda married to her already. But if that should ever change…”
Jeff and Maeve lay in bed talking for an hour or more. He kissed her red lips sweetly. Somehow, he hadn’t gotten around to much kissing earlier, but now they enjoyed a bit of gentle touching and caressing. They learned a lot about each other in that time.
“I’ve been faithful to Em all these years, except for one time. I got a come-on from a coworker, and like a fool I strayed. Just the one time, but I felt so guilty that I confessed to Em. I honestly didn’t know if she would kick me out, but I couldn’t stand the guilt. She was really quiet, and it unnerved me. I was waiting for an explosion, and it didn’t come. Finally, she told me that since I’d cheated, she had to cheat to make us even. I don’t think she wanted to cheat. She understood that making me feel what she felt would ensure that I never did it again. So, one night she announced that she was not going to be home, and I understood she going to be with someone else.”
Maeve sighed, “Yeah, I remember that night. Fondly.”
“She told you about that? I didn’t think she’d ever tell anyone. I never found out who she was with. Not sure I want to know. We’re good now,” he replied.
“Jeffrey, Emily was with me that night. What? You think you’re the only one who likes these boobs?”
He sat up, mouth open, but no words came out. Then he said, “God, you live with a woman all these years and you think you know her!”
“Are you mad?”
Jeff chuckled. “No, but I will be if you don’t invite me along next time!”
At Maeve’s house, things were moving rather slowly. The plan had been for them to begin right way so that Jeff wouldn’t be able to stop them. But when it really came down to fucking her son, Emily balked. It could go so wrong in a million different ways. She could screw up her marriage, her son, herself. Emily spent a long time explaining female agent porno sexual etiquette, condoms, dating, and lots of other things that Ed already understood. She was stalling, and he knew it.
“Mom, if Dad was gonna try and stop this, he would be here by now. Let’s get on with the plan, okay? Or, you can back out, I guess.”
She realized he was right, and like the take-charge woman she was, she finally began the evening’s activities.
“Ed, I think the best thing for us to do is just strip off our clothes and see where this goes. Remember, you can call this off at any time if it starts to bother you,” she said as a last ditch effort to make all this go away. Why had she thought this would work? But this train was rolling now, and unstoppable.
In Maeve’s bedroom, they undressed each other and embraced. Ed’s cock was not shy, and he poked her as they hugged. Not wanting to simply fuck, she maintained control and tried to build up to it gradually. But that’s hard to do with a young man when you’re both nude. She took a step back from him.
“Baby, take a look at me. I’m a middle aged woman, and I never was a swimsuit model. My breasts are small, my hips a bit too wide, and my face is plain. This is what you’re getting, so I hope you’re not too disappointed.”
Disappointed he was not. Speechless, maybe. Truth be told, he’d been sexually attracted to his mom for a long time.
Emily sat on the bed. “You might as well see all I’ve got.” She spread her legs wide and motioned for him to kneel in front of her. Ed rested his palms on tops of her thighs and peered into her pussy. Now, he really was speechless. Her pubes were trimmed, and her pinkness drew him in like a hypnotist swinging a watch.
He looked up at her and asked hoarsely, “Mom, can I kiss you, there?” She could see the hunger and passion in his eyes.
“Sure, Baby. Kiss Mommy’s pussy if you like.”
She was shocked at her how naughty that sounded. But she didn’t have time to dwell on that, as he began gently lipping and tonguing her labia. She put her hand to the back of his head, and within a minute, her head was arching backwards as her juices began flowing and her pussy heated up. Emily would have been happy to let him give her an orgasm this way. She was certainly heading in that direction. The kid was a natural. But this was supposed to be about her son’s pleasure, and so she made him back off.
“Honey, why don’t you get on your back here. I want you to hold out as long as possible this first time so you’ll really enjoy it. I’ll be on top.”
There were condoms on the table, and she unrolled one on his cock as she sat astride his legs. Carefully, she moved forward and placed his dick head at the entrance to her pussy. Emily watched her son’s face as she slowly slipped it inside herself.
He was struggling to maintain his cool by any method he could. His eyes were closed as he tried to think of something neutral. He bit his tongue to the point of pain and concentrated on that. He kept his eyes shut so as not to be overwhelmed by the sight of his naked mom, sitting on his cock.
Emily did not move for a long time, hoping to extend her son’s first fuck. When she felt him relax a little, she allowed her hips to rock a bit. With her pussy warmed up, she felt on her way to a good come, too. She was almost embarrassed at how turned on she was, but she decided not to deny herself. After all, she didn’t know how much this night might ultimately cost her, so why waste the opportunity to get something in return?
Her movements were stronger now, and she rightly anticipated that Ed would not be able to hold out much longer, although he had given it a hell of a try. She leaned forward, hands on his shoulders, to change the angle of penetration and get more contact for her clit. When she felt him about to hit, Emily poured on the steam, taking herself over the edge as he filled the condom with his young come. It was not a quiet climax for either of them, and neither was it a short one, as they squeezed every ounce of pleasure from it. They fell into each other’s arms, huffing and sweaty.
It was a few minutes before either spoke.
“Mom, that was fantastic. I can believe how good a real pussy feels! Your pussy! And, am I wrong or did you come, too?”
“Well, it’s never been a secret that sex can be wonderful. Makes the world go round, you know. And there’s so much more to it than you’ve experienced yet. But to answer your question, yes, you did make me come.”
He seemed to puff up with pride. “I hope there’s more to it tonight…because I’d like to feel you come again.”
“Slow down a bit. We’re in no rush.”
Emily got up to get a hot, wet wash rag to clean them both up. On the way to the bathroom, she picked up her phone and texted a single question mark to Maeve. Before returning to the bedroom, she got back a thumbs up emoticon in return. Looked like things were okay, for now. She wasn’t looking forward to the inevitable meet up tomorrow morning, though.
As she cleaned up Ed and herself, he began talking, idly fondling her breasts and hips.
“Mom, you know I’ve wanted to have sex with you since I can’t remember when. Other girls and women are pretty, sure. But you’re the one woman who really means something to me.”
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