How I Met Your MILF - Cover

How I Met Your MILF

Copyright© 2013 by Lubrican

Chapter 8

Romantic Sex Story: Chapter 8 - Your best friend will always stand by you, and take your side. He will support you even if it embarrasses him. You might disagree on things occasionally, but in the end, all discord falls away. You are best friends. And best friends never get really mad and hold a grudge. Well, not unless you fuck his mother.

Caution: This Romantic Sex Story contains strong sexual content, including mt/Fa   Consensual   Romantic   First   Oral Sex   Pregnancy  

I think one thing that helped was that we went back to my house, and did the regular sleep over thing there. It was a little stiff at first, but then his natural curiosity began to work on him. I mean, think about it. How often do you get to grill the guy who's porking your mom? Or any woman you know and like? That kind of information just isn't easy to come by.

Not that I spilled about what we'd done. It was all done in a sort of code. And I think it helped, if that's the right word, that Scott didn't think of his mother in the same way that I think most boys do. At least boys with two parents. For most boys (and probably girls too) you have a mom and a dad who have always been your mom and dad, and the thought of them doing the bump ugly is just sort of creepy. Nobody wants to think about that.

But there wasn't a dad in Scott's history, at least not one he remembered in any great detail. And his mom hadn't gone out with guys, or had a boyfriend. Moreover she was a babe, and there was nothing threatening to him about admitting that. Remember, he'd seen her naked that night when he also saw the teenaged babysitter naked. So he just didn't think about her like most boys with two parents would think about their mother.

The upshot was that Scott Carson could understand how other guys might consider his mother to be ... a MILF.

How do I know this?

Because that's where our wandering, painful conversation led us that night. It led Scott to a different kind of understanding of why I could fall for his mother. It put things in a frame of reference that made sense.

I think her attempt to point out that my sterling qualities as a human being could be just as attractive to her as they were to him, plus the combination of his understanding of the MILF phenomenon, got him to a place where he could live in this new world without his head exploding.

In fact ... he asked to see the picture again.

I had learned from her.

"You sure?" I asked.

"Yeah," he said.

When it was up on the screen, in blazing, living, not very much color, he stared at it for a long time. I did too, my eyes doing what they had always done when I stared at this picture while I jacked on my prick. I gazed at what looked like a perfect shadow, first at that perfect, pointed nipple, and then at the nebulous tuft of pubic hair. Then my eyes wandered over the curves of the rest of her. Those curves were everywhere. Her back curved into the small of her back just above a full, rounded bottom, and then the sculpted thigh and calves below that. Her hair was curved, and once you got past the bulge of that breast, everything about the front of her was gentle curves too. It just screamed femininity.

"That's my mother?" he sighed.

"Yeah," I sighed back.

"I recognize the hair, now," he said. "And the railing around the deck. How could I have missed that?"

"I don't know," I said, still staring at the screen.

"She really is a MILF," he said.

"She's your mother," I reminded him.

He looked at me. "Yeah, but she's your MILF."

"Actually, technically, she's your MILF," I said.

"You're creeping me out, man," he said, but his heart wasn't in it. "Did you really ... do it ... with her?"

"I don't think she'd be happy if I answered that," I said.

"What was it like?" he asked, looking back at the computer screen.

"Unbelievable," I sighed.

He looked over at me and then walked away.

"Remember how we used to sit around and dream of what it would be like?"

"It was nothing like that," I said.

"How could it be nothing like it?" he asked.

"It was better."

"What do you mean?" he asked.

"I can't explain it." I saw him frown. "I'm not trying to dodge the question. I really can't explain it. I mean I can't put it into words."

"Try," he pleaded.

I thought about it, and the only thing I could come up with was something we'd talked about before.

"You know how when you wake up with a boner, it feels good to press it into the bed, and maybe move it around a little?"

He nodded.

"It's like the difference between doing that ... and jacking off."

He blinked about three times.

"Wow," he said.

"Yeah," I said back.

"I gotta get me a girlfriend," he sighed.

"You really do," I said.

And that was it. He suggested we play Black Ops, and we did that until it was time for supper. After supper he said Coach wanted them to run more, so we went for a run. He was in better shape than me because of all that football practice, and he ran me into the ground. I finally stopped, bent over, hands on my knees, gasping for air and worried I might throw up. He came back and ran in little circles around me, taunting me.

"Come on, man, my mom deserves better than that."

"Shut up," I panted.

"Women want a guy with stamina," he jeered.

I was tempted to tell him I'd fucked his mother at least six times in one night while he was drugged out on the couch, but I didn't.

"Shut up," I said instead.

"They do," he insisted.

"They also want a man who's alive," I shot back.

He laughed. It was the first time I'd heard him laugh in a week, and it felt good to hear that. It was enough that I stood up and started off again. At a much slower pace. He ragged on me about that too, but I ignored him. When we got back, my mom and dad said they'd take us to Dairy Queen for a Blizzard, on them.

The whole time we were there, Scott's eyes never stopped roaming over the women in the place. Three times he nudged me and leaned over to point under the table and whisper "MILF."

I didn't know whether he had adjusted ... or was trying to make me feel bad.


What Scott was thinking, was important to his mother. I knew it would be, but I didn't know whether she'd want to cool things down for a while, that soon after things blew up. I worried that I might not be welcome yet. I went anyway, right after school.

The question of welcome was answered by a big hug and a delightful kiss, as soon as I walked into the house.

Then she dragged me into the bedroom, where she stripped me naked. It's kind of ironic that they call it a blow job, and that the action takes place way down there, but the blowing part happens in your brain. I really thought my head was going to explode at one point.

That's because when I told her I was cumming, she pulled off and squeezed the base of my cock, and suddenly I couldn't cum. It was painful. Then she blew me some more, and did it again. It took four times before I realized what she was doing.

"I'm sorry!" I groaned. "I had to give him something or he'd never have given up. He might even have followed me around and caught us."

"You had to be punished. You promised and you broke your word. Don't do that to me again, Bobby. Besides, we weren't doing anything back then to get caught at."

"If he'd have started watching me more closely, he'd have seen how I looked at you," I argued.

"I saw how you looked at me," she sighed. "It made me crazy. I fought it, but it was hard."

"I'm really sorry," I said.

"I know," she said. She went back to work on me and this time, when I blasted, she gobbled it all down and smacked her lips.

Then she interrogated me about what had happened at the sleep over at my house. She would have made a great CIA agent or whatever those people are who interrogate terrorists. She left no stone unturned, even asking what I thought things meant, and why I thought that.

It sounds like it wasn't the best of meetings, except that she did all this questioning naked, with me on top of her, also naked, and my cock sliding in and out of her. There were pauses for orgasms, mostly hers. Twice she said "Don't cum yet, we're not finished." Both times I went in deep and stayed there, resting, while her hands got my hips moving in circles. She had orgasms when I did that.

"You know, it's really not fair that you get to have four or five orgasms to my one," I said, as she relaxed from an orgasm, and before she started asking me more questions about how Scott was taking all this.

"What's not fair is that I'm the one whose belly will get all swollen up, and I'll have to waddle around with an aching back for months, and then spend eighteen to twenty-four hours of labor in excruciating pain just to give birth to your son." She squeezed my penis with those incredible internal muscles she had. "It takes a man ten seconds to make a baby. It costs a woman nine months of her life to deliver it. I think we should be compensated accordingly."

She looked at the shock on my face, which was there because that was the first time - I swear! - that I had given even one second of thought to the possible consequences of what we were doing. I know that sounds crazy, but it was true. I hadn't thought even once about the possibility of getting Mrs. Janet Carson pregnant. Maybe that's why there are so many teenage girls out there who get knocked up. Teenagers don't think about that stuff.

"You're going to have a baby?" I squeaked.

She smiled. "Well ... no ... but I could. That is, after all, what Mother Nature intends this particular activity to result in."

"So you're not pregnant?"

"Not yet," she said, still making my hips move in little circles.

"Aren't you on birth control?" I asked.

She stared up at my face. "Bobby, I don't have sex with men. There is no man in my life. Why would I need to take birth control pills?"

"You're having sex with me right now," I yelped. "I'm the man in your life!"

She smiled. "Well, I suppose things have changed a bit since last month. Maybe I should re-think my position."

"Ya think?" I gasped.

"Actually ... I think I like this position very much." Her hands started me in circles again.

I was upset. At least I think I was upset. I was all tight inside. The idea of her having my baby rattled my brain. I couldn't make a baby! I mean that was ridiculous. I was too young to be a father. My mother would kill me! All that angst caused my motions to be a little more aggressive than they had been. In fact, they were a lot more aggressive.

"Ohhhh I love it when you do it like that," she moaned, wiggling under me. "Don't stop, baby, I'm gonna cum."

She did too, and suddenly, for reasons I didn't understand then, all I could think about was shooting in her. It was crazy, because I didn't want to make a baby, and I didn't want to be a father. But all I could think about was trying like the blazes to get her pregnant.

Since then, of course, it's been explained to me. My biology professor in college was a great guy, who was older and looked like Albert Einstein. He was very approachable, probably because it was a small college and he didn't have thousands of students to deal with. Anyway, I asked him about that phenomenon and he explained that the biological urge to procreate ignores social and cultural restrictions, if the consequences are tolerable. He said birth control needs to be taken care of long before the act commences, because otherwise nature tends to make us forget all about it.

Anyway, she had her orgasm, and I cried and whined my way through mine, like a little girl or something, begging her to never stop loving me and stuff like that. Her hands were all over my back, and she murmured things to me that made me want to keep shooting long after I had given her every drop in my balls. I collapsed on her lovely, soft, warm body, and her hands kept stroking my back while she told me she loved me.

We were dressed and presentable again, waiting for Scott's imminent arrival and trying to act like we hadn't just fucked each other's brains out, when that "issue" popped back into my mind.

"Are you really not on birth control?" I asked.

"Of course not," she said.

"Not even since last week?"

"Haven't had time to go to the doctor," she said. "I have this big project at work that I can't take time off from."

"But you just let me..." I didn't finish, but my meaning was obvious.

"Lover," she said, (my dick lurched in my pants at just that one word) "I wouldn't have let you do anything at all unless I loved you enough to have your baby." She yawned. I would learn that she liked to take a nap after sex, something else Mother Nature encourages in a woman with a pussy full of sperm. When she spoke next it was with a casual tone that made me shiver. "No man's penis will ever get inside me unless I love him enough to have his baby."

To me, that meant there might be other men. I remembered her comment about me forgetting her while I was at college. Suddenly my stomach hurt.

Scott pounded into the house just then. Mrs. Carson and I were both standing in the kitchen, drinking juice. What he saw was his mother looking tired, and me looking like my stomach hurt. I didn't realize that until I had been dragged to his room and he said "What's the matter? She wouldn't give you any today, or something?"

This will give you some idea of how strong and viable our friendship was. I told him what I'd been thinking. I didn't tell him what we had done, just that I was scared that when I went to college, she'd assume I was going to find another girlfriend, and that she might find another man because of that. I was all jacked up about it, crying and everything.

He let me go on, spilling my guts about being afraid his mother might fuck somebody besides me. I didn't say it in those words, but that's what I meant and he knew it.

"Stop," he finally said. I thought he didn't want to hear about me and his mother, but I was wrong. "You know her better than that. She would never cheat on you." He blinked, and frowned. "At least not without telling you she was going to. She's loyal, and if she says she loves you, you can take that to the bank. And I know you too. No girl at college is going to have a chance with you. There isn't anybody I know who is as loyal and faithful as you. So stop worrying. Go to college. Get a degree. Grow some facial hair. Then you can come home and marry my mother. Okay?"

I was stunned. I was slack-jawed. It was incredible.

"What you need to worry about," he went on, "is why she's pissed enough at you to cut you off. You need to apologize for whatever bone-headed thing you did, or get her some flowers or something."

"She didn't cut me off," I said, without thinking. We were friends. We talked like that all the time.

"Really?" He looked interested. "You just looked so down I thought she wouldn't let you ... you know."

I had recovered enough to try to answer with some tact.

"That wasn't the problem," I said. "I was just worried."

"So she didn't cut you off?" he asked. His voice sounded funny.

"Nope."

"What time did you get here today?" he asked, entirely too casually.

"I came here right after school," I said.

"So you've been here for like two hours?"

"Yeah," I said.

"And were you all worried like this the whole time?"

"No," I answered. "You want to know what I was doing all that time?"

His face paled a bit, and he swallowed.

"I guess not," he said.

"I thought so."


The next hurdle was the next sleepover I did at their house. It turned out to be a pretty low hurdle. I think it was actually more on Scott's mind than ours. We played a board game that night after supper, instead of watching TV, or playing a video game while Mrs. Carson read or painted.

Scott had been kind of jumpy the whole time when he got home from practice. After that Monday, he hadn't asked me what time I got to his house to wait for him. He didn't want to know. The fact was that Mrs. Carson and I didn't have sex every day. Far from it. I had a lot of homework Tuesday, and didn't go over at all. When I got there Wednesday, I got a hug and kiss, both delightful, but then she ignored me while she went line by line through a recipe in a thick cookbook to make some new dish. Thursday, she gave me one of those mind-blowing blow jobs (that really must be why "blow" is in the name, ) but that was all. So we hadn't had sex all week, really, at least not as defined by one of our former presidents.

But he didn't know that. Even if he had, he would have assumed (as I did) that something would happen that night. When we finished the third game, he finally gave up and did a fake stretch and yawn.

"I'm bushed. I think I'll hit the sack. Want me to leave the light on for you?" He looked at me.

"Sure," I said. "I'm not tired yet."

His eyes bugged out a little, probably because he couldn't help but think about what I might do with his mother to get tired, but he recovered.

"Okay, then," he said. He got up and went to his mother, who gave him the same good night hug and kiss she had every night I had known them.

"I love you," she said, squeezing him.

"I know," he replied. He stood up, looking nervous. "What if I can't sleep?"

She got up and went to the shelf where all her art books were arranged. She pulled out a big, thick one, about how to draw human figures. It had lots of step by step drawings, some of which consisted of only one or two lines.

"If you have trouble getting to sleep, read this," she said, handing it to him. "It'll bore you to sleep."

He looked pretty miserable, but he took the book.

"Okay. Night."

"Night, night, sweetheart," she said.

We sat there for a long time after he left, just looking at each other. Finally she spoke.

"What do you think?"

I wasn't quite adult enough to answer that one, and I admitted it.

"I have no idea what to think."

She smiled. "Want to sit on the couch and neck?"

She made it sound so innocent. Suddenly, that's exactly what I wanted to do.

I don't know whether she decided to draw things out because she liked doing that to build things to a fever pitch, or because she thought if it took two hours to get to bed, Scott would for sure be asleep by then. But we sat on that couch and played with each other for an hour before a single piece of clothing was removed. Even then, all she did was take off her bra and let me slide my hand inside her shirt to play. She'd worn a skirt that evening, sans panties, but she kept batting my hand away from there. She did let me stroke her bottom, but every time I tried to get my hand between her legs she closed them and whispered, "Not yet, stud," or "Don't be impatient," or something like that. All she did for me, other than sucking my brains out through my tongue, of course, was to gently pat and stroke the outside of my pants, playing with my boner.

Then, as if a switch had been thrown, she lay back and opened her legs. With little whispers, she taught me what to do with my fingers to give her an orgasm. It was awesome. It made me feel powerful, somehow. After that her shirt came up, and I sucked her nipples while I circled her clit with a fingertip, or rubbed three stiffened fingers across her distended little bump with a whipping motion.

She let me play with her body like that for another half hour, just lying back and having little, jerking orgasms. At one point I had my finger deep inside her, crooked to tickle the top of her channel, where she said there was a special spot that, if I could find it, and tease it just right, would make her crazy. Apparently I did, because she grabbed a pillow and held it over her face as her hips jerked and her belly muscles went tight as she lifted her butt up off the couch cushion. Her hand went to grab my wrist and she held me still until she relaxed.

"Too sensitive," she panted, as she moved my hand slowly away from her body, drawing my finger out in tiny increments. I was amazed that if felt like there was some kind of glue inside her that didn't want to let go of my finger.

She kissed me some more, and then opened my pants to suck my erection. She just played with it, really, not trying to make it squirt. She did that for fifteen minutes. Finally she lifted her head and looked at me.

"I need you," she said. "I need you to love me."

"Yes," I said, my voice shaky. I felt stupid. Everything she said made me feel important, and all I could come up with was "Yes?" She didn't notice.

She padded barefoot to Scott's bedroom door and opened it quietly, peeking in. She turned off the light, and came back to lead me to her bedroom.

She taught me how to make love to her pussy with my mouth.

It was easy. She'd showed me how to do it for the last fifteen minutes. The equipment I was using on her was different, but the technique was the same. I kissed, and licked and sucked, just like she had. It took me five or ten minutes, but I knew I was doing it right because within two of those minutes she had a pillow firmly covering her head. When her hips bucked up off the bed, and a muffled sound like she was being tortured came through the pillow, I knew I had gotten her there.

My face was suddenly wet, which was a surprise. I didn't know women expelled fluids too.

And it tasted luscious to boot.


She let me give her three orgasms like that, and then stopped me. She reached for me and lifted her knees and heels off the bed, spreading her thighs to open herself in welcome.

"I need you in me, now," she panted.

As I got into position she rested her heels on my shoulders. It was only the second time I'd done it this way, but there was something primal about that position. It left her basically helpless, in terms of regulating how deep the penetration was, or preventing me from dumping my balls into her. Her hands could grip my arms, but if I pushed deep, it bent her back so that she had no power in her arms to push me off. That she chose that position herself was a powerful message that she welcomed me with no reservations, that she trusted me, and was willing to put herself in my care.

I think she already had my number, because as soon as I got in her good and deep, pushing that rubbery thing to the side, she started whispering things to me about how much she loved me, and how much she loved having me deep inside her, and for me to never stop and all that kind of thing.

And she used my phobia about her first name against me too.

"You gonna squirt in Janet's pussy?" she whispered, squeezing her nipples and pulling at them, stretching them away from her body. It looked like it had to hurt, but she was obviously happy. "You gonna fill up Janet with your hot stuff?"

Just fucking my best friend's mother was taboo enough to make this incredibly exciting. The fact that she loved me made it even harder not to spurt. But when she encouraged me to do it, it was impossible not to.

With a groan I pushed so hard I could hear her rasping to get air into her lungs, and I tried to find muscles to pump my sperm into her faster than I could by just letting my body do it automatically. Again, I whined and cried and acted like a little kid, but she cooed at me about how warm it was, and how good it felt. She said silly things, like after the fourth spurt, when I thought I was done, and ground against her still trying to shoot. And to my surprise, I got another spurt out, and she said "Oh, there's another one! Mmmmm, give me every drop, lover."

That was when I also learned why, in the movies, the guy usually falls off of her to one side, as if he'd been shot by a sniper. That's exactly what I did, making the bed bounce, and flopping onto my back with my arms and legs spread. My left arm lay across her, until she picked it up and moved it between us. She lifted her head.

"You made a mess in me," she said. Then she rolled over, reaching between her legs with one hand while her lips demanded kisses from me. I thought she was diddling herself.

"Are you kidding?" I asked, between kisses. "After that, you're still diddling yourself?"

"I'm not diddling myself," she said. She kissed my cheek.

"What are you doing, then?" I panted.

"I'm holding myself closed, so you don't drip out. I don't know about you, but I don't feel like sleeping on a wet spot."

"Oh," I said.

"Besides," she said. "It doesn't do any good if you let it all drip out."

I think I was already drowsy enough that that comment didn't sink in right then. I would remember it later ... but at that moment in time, I simply wanted to go to sleep.


She didn't wake me up during the night, that night. I think the fact that we'd been able to sleep together, with Scott in the house, made her less frantic to get as much as she could before someone made her stop.

It was also good that Scott was such a hard sleeper, and got up so late. By the time he got up, his mother and I were both dressed and looking as normal as we ever had.

I think that helped him act normal too.

We settled into a kind of rhythm of sorts. Generally speaking, I went over to their house three times a week. On one of those times, we might make love. By the third sleepover at their house, Scott was much better about going to bed.

It was in December that something happened to his natural circadian rhythm, and he woke up early. I was in bed with her, of course, and we were awake, and spooning, with me in front and her behind. She was playing with my penis under the covers. I had a morning hardon, and those were some of the most rigid, and she liked squeezing them. She didn't stroke me, because she knew my bladder was already painful, but she squeezed it, while she rubbed her hot breasts against my back and kissed my shoulder.

Scott came to her room and opened the door while we were doing that. It was chilly, and we were under the covers, so he didn't see anything, except the two of us, next to each other.

"Can I help you?" she said, her voice flat.

"I couldn't find you downstairs," he said.

"Didn't I teach you to knock?" she asked.

"Yeah," he said. "Sorry."

"We'll be down in a minute," she said. "You need to learn to make breakfast anyway."

"Okay," he said.

He closed the door and she got out of bed. She walked around naked, getting her clothes together. She didn't get a piece of clothing and put it on immediately, like most people do. She got everything together and then got dressed. She later told me she did that on purpose, because she loved watching me watch her.

"Get up," she said, eventually. "He can't un-see us. You have to learn to live with that."

It was good advice, and it turned out to be important advice, because I had learned to live with that by the time Scott and I got to college and were roommates, and I learned for the first time that he peeked at us probably four or five times, opening her door just enough to see through the crack, and watched what his best friend did with and to his mother. He said he was lucky the first time he did it, because she was sitting on top of me, rocking slowly, sitting bolt upright so she could get the deepest penetration. He didn't know that, of course. All he knew was that she was in charge, and he couldn't see the penetration. All he could see was her profile from the back, and one breast. So it wasn't so threatening to him, that first time. It had prepared him for the time he peeked and her ankles were on top of my shoulders. He could see everything, that time. That was the last time he watched, because it was almost more than he could take.

But we didn't find out about that for eight months. He came to grips with the situation as well as he could which, thankfully, was quite a lot. More than once I've tried to imagine catching him with my mother. He's a hell of a lot stronger than I am. I can tell you that.

That pattern persisted for the rest of the school year. When you have that kind of thing in your life, school issues don't seem to be all that big a deal. Both she and my parents demanded good grades, and we always studied hard. Graduation kind of snuck up on me, to be honest. I'd been getting stuff from colleges I'd applied to and I think I was already looking beyond graduation before it even happened.

I say I got things from school I had applied to. I should have said schools we applied to, because Scott and I sent in every application together. We had formed a pact in middle school that we'd go to college together, and be roommates and all that kind of thing. My relationship with his mother didn't change that.

We ended up deciding to go to Northwest Missouri State University in Maryville, Missouri. We both wanted to be teachers. I was interested in teaching Math or Science at the high school level. Scott wanted to be a physical education teacher and coach. There were other places we could have gone to get teaching degrees, but Scott chose Northwest Missouri because their team, the Bearcats, had won three NCAA Division II football National championships, the latest being in 2009, and their cheerleading squad had won Universal Cheerleaders Association Division II National championships in 2010, 2012 and 2013. He was desperate to, as he said it, "snag me a hot cheerleader, like my best friend did."

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