Over the past couple months, Jen and Kate had been spending a lot of time together. They had grown as friends. They went shopping together, to the movies, out to lunch and other things. Although Jen, John and Kate had sex together almost every night, Kate became a lot more to Jen than just a sexy little play toy her and her husband fucked in the bedroom. Kate looked up to Jen and was very fond of her as well. Despite their age difference with Kate being 19 and Jen in her 30s, in a way, they became best friends. They hung out together almost all the time.
Jen enjoyed Kate’s company and having her around, especially when John worked late or was away on short, one or two-night business trips where Jen didn’t tag along. Jen and Kate developed a deep bond with each other. Jen enjoyed telling her stories. She even talked with her about all of Jen and John’s sexual adventures. Jen had never told anyone else about her adventurous sex life for fear of judgment, so she was glad she could confide in Kate.
Kate eagerly soaked up the stories. She loved hearing all about Jen’s life. At only 19, she hadn’t experienced much, so her eyes were being opened to so many things through Jen. This was the real schooling that kept Kate’s interest. And Jen was more than happy to educate her.
Jen told her about the men she’d been with, what she liked, what she didn’t, and what to watch out for. Jen gave Kate a lot of advice on various topics as if Kate was her little sister. They also talked a lot about other things like travel, art, books, fashion and pop culture. They had similar tastes and a fair bit in common.
One afternoon they were having coffee at an outdoor café and were talking about sex, typically their favorite topic. Kate was asking Jen all kinds of questions. Her curiosity was overwhelming. She never ran out of questions to ask.
Kate asked, “Where is the craziest place you have had sex?”
Jen thought about it and responded, “That’s a tough one. Maybe in an adult theater. Or maybe bent over the trunk of a car on a public street in Brazil at 3am. I don’t know, there are too many good ones to consider and they have all been different and good for different reasons. Sometimes it was the location. Sometimes it was the person, or persons, I was with. I can’t pick just one.”
Next Kate asked, “John is big down there. Is he the biggest you have been with?”
Jen replied, “John is definitely by far the BEST I’ve been with because we love each other so deeply and are so connected emotionally. Kate, remember an emotional bond is really important and way better than just fucking someone with no connection. But then again, sometimes a meaningless fuck hits the spot when you really need it. But no, he’s not the biggest.”
Kate replied, “Really? Then who was?”
Jen responded, “That would be Pablo. Definitely Pablo.”
Kate asked, “Has John ever gotten jealous of you being with another man?”
Jen replied, “No, we trust each other completely. You have to in a marriage. And our sex adventures are typically about enriching and exploring sexuality as a couple, together. I never let anyone else penetrate me sexually unless John is with me or we talk about it first. Similar to the way the three of us have been having sex every night. It always the three of us, together.”
“Oh, I think I get it,” Kate responded. “So, you never just go have wild sex and fuck some random guy without John knowing?”
Jen answers, “No, that’s an open marriage and we are definitely not about that. Even when I have sex with someone when John isn’t around, we share the experience together later. Our relationship is not for everyone, but it works for us.”
“So, I’m dying to know, how big was Pablo?” Kate asked.
Jen answered, “Pablo must have been 11, maybe even 12 inches long.” Kate looked back at her with wide eyes in amazement and disbelief. Jen continued, “His cock was massive. And he knew how to use it. With the stamina of a 23-year-old, it was sexual heaven. And he was really huge. I mean his girth was really big. I couldn’t even wrap my fingers all the way around it when he was fully hard and I had him in my hand.” Jen continued telling Kate about having sex with Pablo and John, and all her times with Pablo and the exciting and dirty things they did together, and how she would involve John when she was with Pablo alone by showing him videos or telling him about it later.
Kate responded, “Wow, I can’t even imagine having sex with someone that big. Was it difficult? I mean, did it hurt?”
Jen answered, “It was hard to go down on him very far without gagging, that’s for sure. I could barely get his cock in my mouth. But, you learn to relax and take it in. I suppose it hurt a little when he fucked me, but the way he stretched my pussy and filled me up felt so good I never really noticed the pain. Well, maybe a just a little sometimes. When he would stick it in at first. Kinda like anal can hurt sometimes I guess, but just for a second and in a good way.”
“Anal?” Kate exclaimed with shock.
“Have you not done anal?” Jen asked.
“No!” Kate replied.
“Well, I guess that makes sense,” Jen responded. “I think I was 27 before I ever tried it.”
Kate asked, “Doesn’t it hurt?”
Jen answered, “It can sometimes, but it’s a really good kinda hurt. It’s not bad if your partner goes slow and knows what he’s doing. It can feel really good sometimes. John really loves doing it to me too. And if it pleases him, I automatically kind of like it.”
Kate responded, “Really? I never thought about it from the guy’s perspective. I always just thought it would hurt. If John really likes it, maybe I should try it?”
“You can if you like,” Jen remarked. Kate’s last comment made Jen feel warm inside with affection for Kate. She could see that Kate had grown as a person the last couple months. The fact she wanted to please John in a loving manner, and to her own possible discomfort no less, showed that she had really matured from the spoiled brat that first showed up on their doorstep. Jen felt that this was a direct result of Jen taking Kate under her wing and giving her guidance, which it was. She was proud of Kate and the woman she was becoming.
After paying the bill at the café, they got up and Jen said, “Let’s go shopping.” Jen took Kate to the mall and they browsed through several stores looking at clothes. They walked by a lingerie store and Jen said, “Oooh. Let’s go in here. John is going on a business trip on Monday for a couple nights and we’ll surprise him with a special treat when he returns. John really loves lingerie.”
Kate said, “Jen, I’ve never bought any sexy lingerie.”
Jen replied, “Really?”
Kate said, “Ya, the high school guys I’ve been with just want to rip my clothes off as fast as they can and fuck me and its all over in minutes.” They both laughed.
Jen replied, “The sex is way better with lingerie.”
Kate asked, “Really? You can tell?”
Jen answered, “Definitely. John is just a little bit more excited when I wear it for him. I can tell.”
“Wow, I didn’t know,” Kate replied. “I don’t know what to get.”