Jake's Journey
Copyright© 2026 by Mustang
Chapter 1
Erotica Sex Story: Chapter 1 - Growing up in San Diego, California, in the mid-eighties as a sixteen-year-old boy, I had the time of my life. The excitement of learning about how to love a woman came with the help of my mother, her best friend, Anita, and my younger sister, Lindsey. This story was written at the request of reader fan, Frogfur.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa mt/ft mt/Fa Fa/Fa Consensual Drunk/Drugged BiSexual Fiction Cheating Slut Wife Incest Mother Son Sister Gang Bang Anal Sex Cream Pie Double Penetration Exhibitionism First Massage Oral Sex Voyeurism Public Sex
To me, my mom, Dell, short for Dellila, was a hot, sexy babe to perfection. She had just turned thirty-seven and looked ten years younger. She took pride in her appearance and at five foot three, she tipped the scales at about 115 pounds. I knew her ample breasts filled her 34-C bra because of seeing the size tag on them. When I was alone in the house and had jerked off, I’d wipe some residual cum on the inside of her bra cups. Her short auburn-coloured hair accented her beautiful face that matched hazel green eyes and her outgoing personality.
Mom admired me growing into a handsome-looking young man and enjoyed teasing me, especially wearing her skimpy bikini by our swimming pool. She preferred for me to wear my Speedo swimsuit rather than the bulky-looking trunks most boys wore.
I swore that she was giving me views down her low tops or up her short skirts or dresses on purpose. At first I felt self-conscious when I got a hard-on looking at her and fantasized about fucking her and wondered what was on her mind when I smiled, looking.
Lindsey, my fourteen-year-old sister, was a younger version of our mom and was quickly growing into a very pretty young woman. Her 32-C bra would also receive the same treatment when I jerk off and wipe a lot of cum on her bra cups. Her interest in boys was increasing and I wondered if she was still a virgin.
Mom’s girlfriend, Anita, was also married to a sailor and were close friends since both husbands served aboard the same ship. She was another one I compared to Mom in looks and figure.
“Wow, Mom, you look super hot tonight. What a foxy-looking lady!” I exclaimed at the appearance of her wearing her sexiest low-cut, shortest dress.
“Jake, you know it’s hard with your stepdad being away on deployment for six months, so Anita and I like to go out and unwind for a few hours every couple of weeks.”
“At least he isn’t here to treat you like shit. You could have done better than him for another husband.”
“I guess I was still in my weakened stage from the death of your father. God, I miss that man and did he ever love me! He knew about my lifestyle and didn’t object to me working in the escort business.”
“I know, how many mattresses did you and Dad wear out?” I kidded her.
“Several. Thank you for cheering me up,” she said, smiling at me.
“I miss seeing your smile. Is that why Lindsey and I kept Dad’s last name?”
“Yes. Your stepdad didn’t appreciate me being an escort, saying I was nothing more than an overpriced prostitute. I quit working for Dorothy and many times I regret it.”
“I now have plenty of horny sailors to make me smile and appreciate what I have to offer.”
“Mom, I don’t need Jake to babysit me when you go out; I’m old enough to take care of myself.” Lindsey complained.
“I know you think you are, but I’ll feel more comfortable knowing you two are together.”
“Maybe we can agree on a movie to watch together,” I said. My eyes took in her natural beauty in her form-fitting shorts and halter top, which proved she was braless.
“As long as it isn’t a war movie or some other kind I don’t like.”
“I don’t want to be tortured watching another girly movie either,” I countered.
“Okay, you two. I’m sure you can agree on a movie to watch,” Mom said, as if settling the disagreement.
I smiled as Mom approached and leaned over to kiss my forehead. Her right hand rested for a moment on my upper leg for support. My nostrils flared, taking in the scent of her freshly applied chocolate and vanilla perfume. The necklace that normally sat nestled between her ample breasts hung in the air as he felt her soft lips. I had an excellent view at her stunningly low cleavage, her full breasts a breath away from revealing themselves.
“You be good to your sister and try not to tease her too much.”
“I will and I will.”
“You know how I hate it when you pull back on my bra and let it snap against me,” Lindsey complained.
“I can see that you’re not wearing one now.” I smiled.
“I’m not sure what time I’ll be home. You know the drill. It’s not like the nights I stay with Anita, then come home the next day. There’s leftover pizza in the fridge. And just a reminder, it’s Anita’s turn to stay here tonight.”
I knew the drill all too well. There weren’t too many nights that Mom came home alone. With my bedroom door open enough, I could plainly see her in the arms of one and usually two sailors going to her room to fuck her. More often than not I heard her being praised for being such an easy fuck and giving great blowjobs and always swallowing. The next morning I had to make sure she was able to go to work for the lawyer who employed her before I went to school.
Lindsey went and gave her mom a kiss and hug, then waved to her out the living room window as she drove away.
Lindsey returned to me, saying, “You know what Mom and Mrs. Weston will be doing while they’re out, don’t you?”
“I do, but I don’t want to know. I definitely know what she does when she brings men home at night.”
“I feel the same way and know what they do with her in her bedroom. Why does she even bother to stay married to our stepdad?”
“I don’t know. John isn’t very good to Mom and us when he’s home.”
“I agree, and I miss our real dad, his jokes, and his ticklish beard.”
“I don’t miss the beard, but I miss him being home.”
“What movie would you like to watch?” I asked.
“I’m sure you can pick out one I’m not allowed to watch.” She gave him a devilish smile. “I’ll be right back. Will you get us a can of pop each?”
I went to my parent’s bedroom to get the VHS tape and, as a habit, snuck a look out my bedroom window to see if the girl next door was in her room. I first caught a glimpse of her from the waist up and her bare tits reflecting in the mirror on the wall when she dried off from taking a shower or prepared for bed.
I knew Camila was eighteen and the most beautiful Hispanic girl I’d ever seen. Her mother was equally impressive in beauty and figure.
On the odd occasion, I used a long pole to raise her window open several inches and move the curtains open wider. I loved it when, on my silent wishes, she would massage her breasts and rub her nipples to get them hard. As I stroked my cock and most of the time cummed in the cloth I held, I wondered what her other hand movements out of sight were doing.
I looked forward to when my parents’ best friends, Anita and Darrel Weston, come over for a swim and supper. I’d stand to the side of the window in my parent’s room with my cock in hand. Mom and Anita have been close friends since grade school, and that closeness brought them to the enjoyment of swapping husbands. I secretly record them having sex to watch later on.
I would try to take my time stroking my cock as I watch my mom give Darrel a blowjob and swallow his cum and Anita eagerly accepted my dad’s cum. They’d either fuck the other’s wife in the normal position or side-by-side from behind, switching pussies as the wives shared kisses.
Another way was the wife giving a blowjob as they were fucked from behind. One of the best parts was when the husbands relaxed drinking a beer and watching their wives have sex. As I filled the cloth with my cum, I envisioned it was me fucking or receiving a blowjob from my mom and Anita. My real dad’s cock was slightly thicker and longer compared to Darrel’s and I smiled, knowing I inherited the same size too.
I returned to the rec room in time to sit before Lindsey came back. Moments later, my eyes lit up seeing what she was wearing. “You changed into your mini skirt?”
“You don’t like it on me?”
“Of course I do. You have great-looking legs.”
“Thank you. I figured if we’re watching a movie I’m not supposed to see, then I want to sit in comfort. The crotch of my shorts presses against my pussy.”
“Lucky shorts.
“You didn’t have to tell me that, but I’m glad you did.”
“What movie are we watching?”
“It’s one of Mom and Dad’s porn movies. It has several on it. One is called ‘Secrets Laid Bare.’ I took a moment to read the back of the cover about the movie. “I guess two female spies were captured by a rival organization. They have to be fucked and give blowjobs an unknown number of times, which activates something in their pussies to reveal their secrets.”
“That sounds ridiculous, but then again, it’s meant to entertain the viewer in a different way.”
“How would you know what ‘in a different way’ means?”
“You’re not the only one who snuck one of our parents’ sex movies to watch.”
“Were you by yourself?”
“No,” Lindsey smiled shyly.
“Who were you with? Which boy?”
“Who says it was a boy? It could have been a girl.” She gave me a very imish smile.
“Who?”
“Wouldn’t you like to know? I might eventually tell you.”
I put the DVD in the player and returned to sit beside Lindsey. I was sure I could see her white panties under the short hem of her skirt.
She smiled at me, shuffling closer so our thighs touched, then took my right hand on her left, resting it high on her leg.
“It looks like it takes place somewhere tropical. You can see the palm trees and sandy beach,” she mentioned.
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