Visiting My Best Friend
Copyright© 2026 by Lubrican
Chapter 2
Coming of Age Sex Story: Chapter 2 - When you were a teenager, did you ever had "a thing" for your best friend's mother? How about for your best friend's sister? How about your own mother and sister? Did you think there was something wrong with you? Did you believe those people who said that kind of thing meant you had a sexual addiction, and needed therapy? Or did you decide you were just a normal teenager, surrounded by hot women and evolution was simply making sure that men wanted to do their part in keeping the species going?
Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa mt/ft Ma/ft mt/Fa Fiction Incest Mother Son Brother Sister Father Daughter Group Sex Orgy Swinging First Masturbation Oral Sex Pregnancy
I was crazy nervous. What was about to happen could go well, or it could go very, very badly. If it went badly, nothing could be done to fix it. Basically, if Jenn rejected being in this kind of family she might just leave and never speak to any of us again. She might even report us to the police.
My role had been discussed with me. The women seemed to think this approach would work. Dad would be in the house, but not in the room with us.
So Jennifer showed up, having been texted by Mom to come home for an important problem.
“Hey!” she said. “What’s up?”
“We have an issue that is very important and we need your help to resolve it.”
She looked confused, but said, “Okay.”
Mom took over.
“We know how close you and Bobby have gotten over the years. He’s been a very good brother and has protected you.”
“How?” asked my sister.
I had told them about the unwritten rules the boys she dated had to follow and now they exposed me to her.
“Your brother has been warning the boys you date that if they make you unhappy, he’s going to make them unhappy.”
Jennifer blinked. She looked at me.
“Is that why no boy will even try to cop a feel?”
I shrugged.
“You little weasel!” she yelled. “I can’t have any fun on dates and it’s all because of you!” Then she frowned. “I thought something was wrong with me, but now I know that wasn’t it, so that part is good, at least.”
“There is more,” said Mom. “Over the years Bobby has developed what we’ll just call romantic feelings toward you. That bothered him so much he came to us to talk about it.”
Jennifer didn’t ask why Mrs. Marshal would be included in all this. She’d find out, soon.
“He feels like he’s a freak, or pervert,” said Mom.
“He also has erotic feelings towards Emma,” said Mrs. Marshal. “Even for me. He’s afraid he’s insane, or has a sexual disease.”
Jennifer snorted.
“Give me a break. Every guy in school wants to bone Emma and me and probably both of you,” she said. “He’s actually pretty normal, if you ask me.”
“Well, we’re very happy to hear that, but there is a little more.”
“How much more could there be? Did you catch him beating off, or something?”
“He went to our husbands, first,” said Mom. “He thought that, as men, they might be able to help him. That’s because both men have, at one time or another, thought of you improperly, too. So they were no help.”
“Both of them?” asked Jenn, her voice breathless. “Daddy, too?”
“Yes, Darling. Things seem to have gotten out of hand and we wanted to talk to you about it before one of the stupid men did something to scare you.”
“Scare me?” Jenn laughed. “I’m not afraid of either of them.” She looked at me. “You, either, twerp,” she said.
“Phil has fantasies about you, too!” I blurted.
“I know that,” she snorted. “He’s so cute when he gets uncomfortable around me.”
“Uncomfortable?” Mom probed.
“When he gets a boner,” my sister said in a stage whisper.
“So you said he’s cute when he gets ... excited. How do you feel about that, though? How do you react emotionally?”
“Phil? He’s a good guy. At the risk of giving my brother a big head, both of them are good guys.”
“So it doesn’t bother you that they want to have sex with you?” asked Mrs. Marshal.
Jennifer blinked. Then she looked at both women.
“What’s going on, here?” she asked. “This isn’t just about Bobby getting horny on me.”
“You’re right,” said Mom. “We’re going to send Bobby out of here and tell you some things about our families that may upset you. But please listen to us, okay?”
“I have to!” she yipped. “I can’t just go to my room and arrange my makeup if something dangerous is going on.”
“Not dangerous,” said Mom. “You are perfectly safe in this family. In fact, not only would Bobby protect you from harm, so would your father and Roger and Phil.”
My sister looked at me.
“Beat it, Twerp. I have a feeling my world might have changed and I need to find out how much.”
So I left and they were in there for half an hour or maybe a little more. I paced, because I had been outed. I got horny for my sister and now she knew it.
Then the door opened. Jenn came out first and she came to me first. She hugged me. It was one of those good, firm, long-lasting hugs, where you can just tell the person giving it to you likes you a lot.
“You’re not a twerp,” she said in my ear. “I’m sorry for calling you that. And thank you for caring so much about me.”
Then she went to dad and she hugged him the same way.
“Naughty, naughty Daddy,” I heard her say.
And when his hands slid down onto her ass, she didn’t complain.
If it is sounding like orgy central, it wasn’t like that at all. Things happened at oozing-molasses speed.
The first thing that happened to me was that I was taking a shower before going to bed and Mom just opened the door and stepped in with me. She took the soap and then rubbed her hands over every square inch of my body. She even told me to lift my feet up so she could wash them, too. She was very calm about all this.
“Your penis is even larger than your father’s, so if either of the girls want to bed you, you must be very gentle with them and go slowly, at first.”
I knew “the girls” meant Jennifer and Emma, but I knew Jenn had already gotten in bed with our father, so she’d been fucked with a big penis. She had made a lot of noise, but it was crystal clear she was having a good time. She was a virgin, but wasn’t hot about staying that way if it was Dad who picked her cherry. I still didn’t think this was all real, notwithstanding my mother naked in the shower with me.
“Now I’m going to teach you how to touch a woman,” she said.
I do remember every second of that, as my hands explored her mature body. Her boobs sagged a little bit, almost the opposite of Mrs. Marshal’s, but they felt so wonderful in my hands as I lifted them and moved them around. She didn’t complain when I sucked her nipples, which were kind of red, on dark maroon areolas. She had me put my fingers inside her and feel for different things. I knew about clits, but had never touched one, of course. And I had heard about something mysterious called a G spot and she taught me what one felt like and how to tickle it. She sucked my dick and when I came she kept sucking and I almost fell down in the shower. Then we started all over again. She wouldn’t let me out of the shower until she had cum three times.
Then we got out and dried off and she took me to my bed and taught me some more about how to touch a woman. She knew I’d be ready again and the part I loved the most was how you touch the inside of a woman’s vagina with your extremely hard penis.
“Ohhhh, yes, Baby,” she moaned as I got almost all of my cock in her. “You’re making Mommy soooo happy.”
Some distant memory of something I had heard made me say, “Can I cum in you?”
“Yes, Darling,” she said, locking her legs around my back. “You can always cum in me.”
I thought that meant she couldn’t have babies anymore.
I had no idea that both women wanted to have a second round of babies to raise, as their first ones matured and left the nest.
I had no idea, when I groaned and flushed my mother full of my sperm, that I might be breeding her.
I didn’t get to fuck either my sister or Emma for over a month. The main reason for that was that Jenn was having sex with Dad and Mr. Marshal. Being made love to by a real man did something in both girls. Maybe it was because they viewed their fathers as men who could have any woman they wanted, and yet they had chosen the girls.
Eventually, though, they ganged up on me. I got a call from my sister telling me to go find Phil and report back to her.
“Why?” I said.
“Never mind why. Just do it before I start calling you Twerp again!”
So I found him and when we got back to her room we found Jenn there. She and Emma were sitting on her queen bed dressed in nightgowns. They were pretty revealing nightgowns.
“We’re having a sleepover,” said Jennifer. “It got kind of boring, so we thought you guys could entertain us.”
Half an hour later I got all but an inch of my dick in my big sister.
She liked it. She made it crystal clear she liked it. And right beside us, Emma made it clear she liked fucking her brother, too.
Both of us guys spurted, and the girls swapped guys.
I got to see my sister sucking my best friend’s dick, trying to get him hard, while his sister sucked my dick for the same reason.
Over a period of a couple of hours both girls got fucked twice by both of us guys.
I did not know I could cum that many times in such a short amount of time.
I didn’t find out “the details” about my penis until I was fucking Mom one time. She was on top and she had already cum three times.
“I want to do something special only your father has been able to do before now,” she panted.
She sat up straight and then bent a little and wiggled her hips. The inch I had never been able to get all the way in any woman suddenly disappeared as she groaned, “Ohhhh, yeahhh. There it is.”
I felt something kind of cuddle the head of my dick. That’s the only way I can explain it. She explained that her cervix had relaxed, allowing my extra inch to slide into her womb.
“If I were to milk you like this, and I was in my fertile time, you’d almost certainly get me pregnant because all your sperm would go directly into my womb, where it would try to find my egg and fertilize it.”
Her pussy was doing something crazy, rippling and squeezing in a way that made me want to cum.
“Are you fertile right now?” I gasped.
She leaned down and kissed me.
“Maybe,” she said, with her lips against mine.
The thought of my mother’s belly swelling up because I had made a baby in her kind of drove me crazy, and I tried to spurt as much as I could into her baby chamber.
“That’s a very special way to make love,” she said, as I began to shrink inside her. “You must always ask a woman if she’s willing to let you do that, especially the girls. Neither of them has ever felt that. Your father has done it to Heather, but not to Emma.”
“Dad has fucked Emma?” I asked, astonished.
“They have made love,” she said, gently. “Animals fuck. We make love.”
“Got it,” I said.
“Are you glad this happened?” she asked, squeezing my semi-soft cock with the same muscles she’d milked it with.
“Yes,” I sighed. “I’m very glad. I feel so much better knowing that my fantasies weren’t terrible.”
“We’ll do this many times before you fly the nest,” she said. “The only thing I won’t do with you is let you stick that thing in my rectum.”
“Wow,” I said. “I didn’t even think about that.”
“It’s something I do with Roger and Phil, but even then only when I’m on my period or very ripe.”
“Wow,” I said. “I can’t imagine that.”
“They’re small enough that it doesn’t hurt.”
“And I’m too big?”
“Honey, you’re way too big. If your father hadn’t made love with Emma a few times I’d tell you not to try with her. As for Jennifer, your father is getting her used to a big penis, so the first time she wants to make love with you and let you do that, just go slow and listen to her.”
“Do you really think she will? Want to let me get it all in her, I mean?”
“Oh, yes. The only reason she hasn’t is because she’s wanted to make love with Daddy for several years, and now she’s overdoing it a bit.”
“So, what do I do, now?” I asked. “I don’t know how to act.”
“Just be yourself,” she said. “They already love you. If you’re plain, old Bobby they’ll all get horny for you. And if they want to make love in that special way, they’ll tell you. Everybody knows you’re long enough to push through a woman’s cervix.”
She kept squeezing me, milking every drop out of me.
“And now they’ll know you’ve actually done it. It’s a very special thing, Bobby, and if a woman lets you do it, it means she really loves you, especially if she isn’t on birth control.”
“Like you?”
“Like all of us, Baby.”
A little caveat or something, here. I bandy about the word “fuck” in this narrative, but that is only because, in my teenage mind, that was a word I was used to. My mother was right. We did not fuck. Well ... okay, most of the time we made love, but every once in a while one of us men would get anxious to fertilize a particular woman and she (they) would almost always welcome being fucked, instead of being made love to. The difference? If we were fucking, the object was to get off as quickly as possible. Then, if there was time, it would transition into making love, the second time. So, in one sense, the women loved “being fucked” because us men were so pathetic and thankful that they would accept us in that way. My mother told me one time that when one of us men got that antsy it made her feel powerful and she loved hearing us beg to cum in her. So if I use the word “fuck” don’t take that to mean it was something that didn’t mean anything. If a woman let us inside her, it meant she wanted us inside her, whether it was urgent or drawn out. And we did love all the women, because, I think, they loved us.