Who Better for Your First Time
Chapter 1

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa, mt/Fa, Consensual, Heterosexual, True Story, Slut Wife, Wife Watching, Incest, Mother, Son, First, Voyeurism, Double Penetration, Big Breasts,

Desc: Coming of Age Sex Story: Chapter 1 - Dad helps son convince Mom that she should be the one

I had to smile as I heard the creak of our bedroom door. "Mom. Are you awake?" Our son was actually putting our plan into action. Having spent a good part of the evening at a local bar with some friends of ours, my wife took a few seconds before she began to stir. "Mom?"

When he finally reached the bed and sat down near his mother, she pulled herself up on her elbow and after a second or two responded. "What's up Sweety?"

"Can we talk?"

"Sure, Sweety. What is it?"

"It's pretty embarassing..." He paused.

"Honey, you know you can ask me anything. What is it?"

"It's about a guy at school."


Another pause.

"He's not trying to get you involved with drugs, is he?" Her voice a bit louder and more emotional.

"No. Not drugs..."

"Well, if not drugs, then what?" She appears to be much more focused by this point.

"Well...", another pause.

"What then? You can tell me."

"It's sex."

"Oh my god. You're gay?!?" If I had truly been sleeping, I have no doubt my wife's last outburst would have awoken me. She glanced back at me, but I continued to pretend to be asleep. Since the small amount of light coming into the room came from the hallway, she really couldn't see me, and since I didn't move she must have been satisfied that I was sleeping.

She tried to make a serious voice. "Not that I would care if you're gay, I am just asking..." She was almost inaudible for this last part, "Are you gay?"

"No. No. God no. I am not gay". He was almost laughing. "It's not that."

"Well then. What is it?" She was back to her normal whispering voice.

"Well ... you see ... I found out ... that he is having sex with his mom."

After several seconds of silence, perhaps to let what he said sink in, my wife responded. "What?" More silence.

"He's just making it up." She continued. "No mother would ever do that. He's pulling your leg."

"No. It's true."

"How do you know it's true? He probably just fantasizes about his mom. It can't be true."

"No, mom, it's true. I have actually seen them."

More silence.

"Who is it? Is it someone I know? Oh my God, what kind of woman would do such a thing. You must be mistaken. You..."

"No. It happened. I was there. I saw it."

"Oh, my ... That is just wrong. Who is it? You need to tell me."

"I promised I wouldn't tell anyone."

"But Jacob, this is something you need to tell. This is child abuse. She is breaking the law. Who is this woman?"

"Sorry, mom. I can't say. I promised. Plus there is more."

"What do you mean more?"

"Well, his Dad is going to be gone this weekend and they want me to come to his house on Saturday."

You could almost hear the cogs turning in my wife's head. With a very suspicious tone, she asked, "Why would they want you to come over?"

"Well, it's like this ... see ... umm ... well ... I don't want to be the last fifteen year old virgin in school."

A long pause showed my wife clearly processing the last five minutes of the conversation. "My God, she would have to be old enough to be ... to be ... my age. Why would a fifteen year old want someone that old?"

"But Mom, she is hot. She's blonde with big boobs, small waist, and a big ole butt."

"You're not seriously considering this. Surely there are girls your own age. What about Melissa? She seemed like a nice girl."

"Mom, girls my age just don't do it for me. They just run around in packs giggling all the time. Plus, I am not ready for a serious girlfriend and you wouldn't want me to just sleep with a girl just to lose my virginity then dump her, would you?"

"Well, of course not. It's just ... just. it's just wrong. You're my baby. You shouldn't even be thinking about this yet."

"Mom, I am fifteen. I have needs. I have someone experienced who is willing to teach me how to be good in bed. I can't get that with someone my age. Plus, she is hot. She has those..."

"Big boobs. Yea, I heard you the first time. There is more to a relationship than big boobs."

"But that's just it. It's not a real relationship. She just wants me for sex."

Another pause.

"Ok. That brings up something. Why you? Does she sleep with all the boys in your grade or what?"

"No. It's not like that. It would just be her and the two of us."

"So, then, answer this. Why you? Why did they decide you were the one?"

I could tell he was trying to remain serious, but it was a struggle. "Well, it's sort of embarrassing."

"How could this conversation become any more embarrassing? Out with it? Why you?"

"Well, it's cause I have a big one - you know - a big penis."

Another pause.

"So my son is now some sort of stud horse. Great."

"So what do you think? I was going to just ask Dad, but I figured I needed a woman's perspective."

"Well, yea. I have no doubt your Dad would approve. Hell, he would be out buying you condoms at this point", which is a true statement.

"So does that mean I can?"

"I never said that. It's just wrong. We should be calling the police right now."

"I promised."

"Yea, I know."


"Just go to bed. We can talk about this tomorrow."

After he left the room, sleep did not come easily for her. I could hear her actually mumbling to herself. This was a critical point in the plan. How would she react? After several minutes, I was almost asleep when I awoke to the sound of the drawer of my wife's bed stand opening. I fell asleep to the gentle rocking of the bed as I lay alongside my wife who was obviously getting full use out of her favorite dildo.

I was awoken a few hours later to find the bed stand light on and my wife sitting next to me, telling me to wake up. "We need to talk".

I look over to the clock. "What the hell. It's 4:30 in the morning."

"I know. I tried to wait but I just have to talk to you." I couldn't help but glance over to her night stand. The drawer was no longer open. I envisioned a large dildo inside that was probably still warm from the workout it must have had. When she is in need of her toy, there is no such thing as a quickie for her. Just by looking at her, I could tell she had little if any sleep that night.

"So wake up."

"I am. Geesh. Let me take a piss at least."

"Ok, ok. Just hurry it up. We need to talk."

Of course I took my time. When I returned to the room, she was almost bouncing on the bed. "So what is it that you felt the need to wake me up at this ungodly hour - on a weekend no less?"

"It's about Jacob."

"Is he ok?" I feigned concern. "Did he sneak out?"

"No. That's not it. It's just that he came in here tonight with some ... well ... with some weird shit to talk about."

"Ok." I waited a few seconds to allow her to process what she was about to say - almost.

"Well, what is it?"

She finally blurts it out. "I think our son is a pervert." I think she half expected me to feint or soemthing. I remained calm.

"Yea, well ... What fourteen year old isn't?" I lay back down as if to go back to sleep.

"He's fifteen now. And what he told me is not normal."

"Ok. What did he say?" I tried to downplay the whole conversation, which only agitated her even more.

She punched me on the arm, and as usual hurt her hand more than my arm. "This is serious."

"Yes. Yes, dear. And we can talk about it in the morning." I was enjoying this.

"Get up. We need to talk about this now."

As if it took every last bit of energy I could muster, I sat up in bed and looked her in the eye. "Why exactly is our son a pervert?"

"He wants to have sex..." I begin to roll my eyes... " ... with a woman my age."

As if that statement explained everything and justified all her current emotions, I simply looked at her "And?"

"Well, he can't do that."

"I gave him the old 'birds and bees' talk already. I am sure he will figure it out."

Her annoyance was building. "You don't understand. It's the mother of one of his school friends." After giving it a bit more thought to try to make me realize the gravity of the situation, she added, "And she's married."

"So he's going to be in a three-way?" I just threw that in.

"No. Well, yea. Well, the husband doesn't know about this."

"Just tell me what he said so I can get back to sleep."

I let her gather her thoughts and she proceeded to tell me the whole conversation. When she was done, I gave her my best "I care" look, and explained, "At least he talked to you about it first. He could have just did it and we would never have known. I assume you are glad he told you."

It seemed as if she was convincing herself more than answering me. "Yea. Yea. Of course I am glad he came to me." She looked at me with a look like I spilled beer on the sofa. "God, who knows what you would have said to him?" I just smiled and let her have her moment.

After a few moments, I asked her "So, what are you going to do?" I had to work this carefully, letting her work this out on her own - with my guidance of course.

"Obviously I can't let him do this. As far as we know he could get a disease."

"Very true." I let her continue.

"Of course, if I tell him straight out he can't who knows if he will listen. I can't very well keep him locked up in our house forever." She was pacing now.


"Plus I can't discourage him from telling me important things in the future."

"Yea. For sure."

"If only I knew who she was?"

"Did you ask him?"

"Well of course I asked him. You think I am stupid. He promised not to tell." More pacing, "I am sure she is some two-bit floozy who will end up hurting him." She paused in thought. "I bet it's that slut Angela Jackson. She's blonde with big tits."

I pretended like this was new news to me. "So she's a blonde?"

"Yea, apparently with big tits."

"Interesting..." I said with my best smug attitude.


"Oh, nothing."

"Out with it. What are you getting at?"

"Well, have you looked at yourself in the mirror lately?"

"What does that mean?"

"You are blonde. You have big tits."

She looked at me like I was planning to kill her cat. "What are you getting at?"

"I didn't want to say anything, but it's obvious our son has the hots for you."

"Don't be ridiculous".

"Ok." I resigned myself. "Whatever. I am going back to bed."

"But what about this?"

"We can talk more tomorrow. I need to go to bed." Which at this point I did.

After laying there a couple of minutes, she asked me, "You really think he has the hots for me?"

"I do."

"You don't think that is weird."

"Most ... Probably ALL boys do at one time or another. Face it Dear, you're a MILF."


I cut her off. "Goodnight, Dear."

I awoke late the next morning to the smell of bacon. It had been a long time since my wife got up on a Saturday and made us breakfast. This was getting interesting.

She must have heard me get up because as I was heading for the bathroom, she yelled up to let me know breakfast would be ready soon and for me to wake up Jacob. So I did, then I went in to take a quick shower.

When I entered the kitchen, my son was manning the toaster as my wife was finishing up some eggs on the stove. When she turned towards the table, I had to smile. I immediately noticed that my wife had showered and put on makeup already this morning - something that rarely happened on mornings she didn't have to go to work. She had on her nicest silk robe which, while covering her negligee, left ample cleavage and clearly showed off what were obviously hard nipples poking through the material.

She looked at me, obviously gauging my reaction. This was as outfit that rarely left the bedroom. "You look nice." She smiled back and continued with her tasks at hand. I noticed our son sneak a glance at his mom. "Don't you think your mom looks nice this morning, Jake?" I asked.

"Oh yea, Mom. You look real nice."

She smiled at him and said "Why thank you Sir", and then gave him a little curtsey.

Breakfast went amazingly well. We laughed and reminisced long after the food was eaten, the table cleared, and the dishes done. My wife did not seem to notice that her robe had worked its way open and that her near transparent negligee did little to hide her cantaloupe size breasts with hardened nipples the size of grapes. On a scale of one to ten, my wife's breasts were easily a twelve.

Not that he could have stopped anyway [God knows I couldn't], my wife chose to ignore that our son's eyes seemed to be locked on to each jiggle of her breasts.

I was the one who finally put an end to our family bonding moment. "You know Champ, that garage ain't going to clean itself today."

"Yea. I should probably get cleaning in here."

Everyone got up to move on to their day.

"One more thing..." I said.

"Jake, your mom told me about your talk last night."

Although she spoke no words, it was clear from her expression my wife was saying "WTF are you doing?"

I ignored her and continued on. "I want to throw something out here. I want you both to listen to what I have to say and take some time to think about it." I paused briefly. "Once you both have had a chance to think it over, then you can let me know directly. If either of you don't like what I am about to say, then we will just move on as if it was never brought up." After seeing I clearly had both of their attention I continued. "Ok. Just to be clear I will say my piece without interruption and then we will not discuss it until I talk to each of you later tonight. Is this something you both can do?"

They both looked at me suspiciously, but both nodded in agreement.

"Ok. Here goes," I started. "Jake, we want your first time to be someone you care about and trust, someone who won't end up hurting you. I think I have come up with a solution that may at first seem 'out there' but I want you both to take the time to at least think about it, because believe me, logically it makes sense. I think you, Lisa, should be Jake's first."

My wife immediately started to talk when I put up my hand, "No, no. You agreed to at least think about it." After struggling to remain silent, my wife finally makes a quick exit from the room. When we heard the bedroom door upstairs close, my son asked, "You think she will?"

"I have no doubt she wants to. I just gave her a way to save face. Now no matter what happens, it wasn't 'her idea'. It will take a while for her to come to terms with it all but, yea, I think she will come around. I think our plan may just work." I held up my hand so my son could give me a 'high five'.

My son and I spent the rest of the morning cleaning out the garage. We took all those boxes that had been sitting there for weeks to the local "Good Will" and managed to get all the tools put away. Typically my wife would be out there 'supervising' our efforts, but she made no appearance, until finally, she opened the door to tell us to clean up as she going to make us some sandwiches.

When we entered the kitchen a few minutes later, she was in the process of putting stuff back in the refrigerator. "After that big breakfast, I figured you could get by with ham sandwiches. Jake, why don't you grab some chips out of the pantry." She was now dressed in shorts and a t-shirt which was normal, except for the fact that she obviously wore no bra underneath.

At first, things were a bit tense, but slowly things returned to normal. Actually, like this morning, it was better than normal. Normal used to be we would sit down, each of us would list off what we did that day, and then we would leave to go do our own thing. Now, we sat here as three people who genuinely wanted to spend time together. It was nice.

The three of us spent the rest of the day working on the yard. We managed to take care of all those little extras you have to do but can easily put off until later. We even managed to wash the car. Old man Quincy almost hit our mailbox with his bike when he caught sight of my wife in her wet shirt.

"You know, you may need a permit for those things," I told my wife. When she failed to catch on, I stared down at her chest until she figured it out. My son, who was already trying not to laugh, lost it at that point.

"Good one, Dad"

My wife just shook her head, but smiled. "Boys," as if that explained it all.

The rest of the day was uneventful. At the end of the day, we went in to clean up, ordered take-out Chinese food, and watched a bit of TV before bed.

Things were quiet between us as we both got ready for bed. However, when I got in, rolled over away from her, and told her "Good Night", she spoke.

"I don't think so..."

I feigned ignorance, "Huh?"

"You know we need to talk."

"Oh, so you have had a chance to think about what I said?"

"Well, yea. Sorda' hard not to, ya' think?"

I rolled over to give her my full attention, "So?"

"You don't think this is just too weird?"

"Yea, probably, but so what?"

I patiently waited. A couple of times she started to speak, but then stopped. Finally, she says, "So do you think this is truly what's best for Jacob?"

I looked her straight in the eyes. "I do."

"We don't even know this is what Jake wants. It's not like he would even want an old broad like me."

"Oh, no. He is definitely on board with this."

"Really? You talked? What did he say?"

"All I am going to say is he wants nothing more than for you to be his first. I guarantee that."

She pondered this new information. "Well, I can't guarantee I will be able to go through with it, but I guess I will try."

I leaned in and kissed her. I immediately noticed her lips were quivering. When our lips touched, her nostrils flared as she made a quick intake of air. When my hand reached up and grabbed her boob, her body actually began to shake. She was having an orgasm. I have never seen her so horny.

For the first time in years, we stayed up all night fucking like bunnies. There was no "making love" that night. It was a loud, hard core, in your face, fuck session.

I awoke the next morning from a weird but amazing dream that involved Dolly Parton of all people. In the dream, I was complaining that I was too sore and to stop sucking on my dick, but she only laughed and kept sucking. I am not a big fan of Dolly per se, so I am not sure why she was in my dream. Just as I felt my orgasm trigger, I awoke to find my wife's head bobbing between my legs – an odd combination of pleasure and pain because I truly was sore from the night before.

Once she seemed satisfied that she had gotten every drop, she bounced up and sat beside me on the bed, "So how is this going to happen?"

"Well," I sat up in bed beside her. "I figured we would wait until Saturday so we can make this extra special."

"Well Mr. 'Always Have a Plan', what's your plan?"

"The Rep from one of our main distributors is getting married Saturday up in Kansas City this Saturday. I think I can get him to give us an invite at least to the reception. That will give us a reason to dress up, get a nice meal, and even do some dancing."

"Dancing sounds nice, but isn't this supposed to be Jake's night?"

"Who do you think is going to be his date? I am going solo."

"But I don't know this guy. No one will know us."

"Exactly. You will be free to do as you wish. When a hot babe like you walks into a place like that, no one is going to question whether or not you belong, especially when you walk in with your son."

She seemed pleased with this plan. Then a thought came to her, "Wait a sec, what's to keep you from picking up some strange at this shin-dig?" She looked at me half-smiling but then tried to get serious. "You don't have some floozy you plan on hooking up, do you?"

"No. This is Jake's night and I wouldn't miss it for the world. Besides, at the rate you're going, I will be lucky to walk by Saturday." She laughed at this as she headed to the bathroom.

The next week seemed to be nothing but sex. Not that I was going to complain. She would get so worked up teasing the poor boy. We had more sex in one week than probably the last five years combined. Poor Jacob spent many an hour in the bathroom.

Saturday morning finally arrived. Since we all packed the night before, we just had to throw everything into the car and take off. We would change into our wedding clothes once we got to the hotel. Since my wife was nervous about crashing the wedding party, I came up with a cover for them both. Her husband was Jay Johnson from the St Louis office, and Jay had to go back to his office unexpectantly this morning. There more than likely wasn't a Jay Johnson at the St Louis office, but since the groom was a salesman, he would never openly admit to not remembering someone from the office of his biggest account. As planned, Lisa and Jake took a taxi to the reception while I followed in our car.

Chapter 2 »