Chapter 6: Sex Mentors - Rose

Late evening, March 15, 2011

Before she started her story, Rose had Tom and Jessica sit on his bed while the two of us sat on mine. Once the four of us were in position, she started, “My story is somewhat similar, but a lot less stressful for me, and the really bad part only lasted a couple of weeks instead of a couple of months. It began shortly after you returned to Texas after my fourteenth birthday last year.”

Rose paused for a moment before continuing, “I started to visit couple of Mom and Dad’s friends, who tonight I will call Sally and Art. After the second or third visit, they started mentoring me about sex. Sally was the first person to lick my pussy and hers was the first one I licked. The first blowjob I ever gave was to Art a few days later on his birthday. Art was also the recipient of my pussy cherry a few weeks later. Someone else, who shall remain nameless at the moment, was the first to enter my ass though.”

“Based on your wording, it wasn’t your boyfriend.” Tom speculated.

“That is correct. Besides those first times, they taught me a lot about how to give pleasure to both women and men. I have found that I like both genders, either in a one-on-one encounter, in small groups, and on occasion in some not very small groups. Most importantly, they helped me discover a lot about my body. While I have not gotten permission to tell you who they are, but I can tell you that the three of you have met them and their children.” Rose stated.

“Like Jessica, shortly after Art fucked my pussy for the first time, I started to wonder what my parents might do to me if they found out I was having sex with their friends. The first time I asked Sally about it, she responded much like Lucy had, saying something like, ‘your mom knows what she needed to know.’ About a week after the first time I asked that question, I spent the night at Art and Sally’s home for the first time.” Rose continued.

Looking into her eyes I could see how the memory was affecting her, “The next morning I woke up some time after Sally had gotten up, but before Art. After getting up I headed towards the kitchen still nude, I paused just outside the kitchen when I overheard Sally talking about the previous night to my parents. I waited until she hung up and then I confronted her again about what she was telling my parents. This time I told her that I had accidentally overheard part of the conversation.”

“She once again told me that ‘my mom knew what she needed to know.’ I went back to their bedroom and got dressed. I then put my dirty clothes in my backpack, leaving out the lingerie Sally had given me the night before. Returning to the kitchen, I asked Sally to tell Art goodbye for me. I also told her to tell him that it was nice spending time with them while it lasted.” Rose continued.

“Sounds familiar,” I interrupted.

Pretending the interruption hadn’t occurred, Rose continued, “Sally asked me what was wrong. I considered repeating her words. Instead, I told her that since she refused to tell me what she had been telling Mom, it could only mean that I was already in bad trouble with my parents. I also told her I figured I probably would be in even worse trouble when my parents found out what was happening between us if they didn’t know already. I figured that in the best-case scenario, when I got home I would face one of two alternatives, either being grounded for years, or being disowned which might include being put up for adoption in another state. I also figured that depending on how mad Mom was, that Mom might try to tell the cops that she and her husband had kidnapped and raped me.”

“I sometimes wish I had done the same thing after the first night I slept with Bob,” Jessica interjected.

Smirking at Jessica, Rose continued, “Sally quickly admitted she had been telling Mom what we had been doing all along. I also found out that Mom not only approved of what had happened so far, but she actually had given some suggestions of things to try. Seeing as Mom had been encouraging me to visit Sally I decided to give her at least the benefit of the doubt at the time. Sally then asked that I stay for breakfast, then they would take me home and tell my parents what happened. I reluctantly agreed. I intended to sulk while Sally fixed breakfast, but out of force of habit, started helping her prepare it. When the food was almost ready, Sally asked me to wake up Art while she finished things up in the kitchen.”

Rose sighed before continuing her monologue. “The night before the relationship with my mentors changed, Sally and I had talked about waking Art up with a double blowjob. Instead, he woke up with me shaking him, much like I used to wake the two of you up. He opened his mouth as if he wanted to say something, but shut it on seeing my expression. After what seemed to be several minutes, but likely was less than one, Art told me that if I wanted to talk he would be willing to listen. The only thing I told him at the time was that breakfast was almost ready.”

“During- breakfast the Art and Sally tried to engage me in conversation, but were I didn’t say anything but ‘pass this or that.’ After breakfast they took me home, still trying to get me to talk, the only thing I said was ‘thank you’ once I got out of the car after we arrived here ... Sally got out of the car and told my parents that I needed them before saying ‘so long’ before heading back to their home.” Rose continued.

I wondered if Rose’s reaction had caused her to be punished as she continued her story, “Mom and Dad took me to their bed, where we spent most of the day just laying down with them hugging me. My parents kept gently telling me they loved me no matter what happened. I was in a better mood by the time for evening chores, so Dad and I worked on them while Mom started dinner. When the chores were done, I went to the kitchen to help Mom, but she had already finished preparing the meal.

“While we waited for Dad to get cleaned up, Mom told me that she knew Sally’s side of the story. Mom then asked that I share my side as well. I admitted I was sexually active with both Art and Sally by my choice. I then explained my fears, and how those fears grew with Sally’s non-response to my question. Mom reminded me that she loved me and that she would never consider disowning me, even if I did things that disappointed her.

“Mom then asked me if I liked how things were going with my mentors. I admitted to enjoying things somewhat, but that in some ways I felt afraid of enjoying myself. Mom then asked if I thought that my fear of being punished was causing me to be afraid of enjoying myself. After thinking for a minute, I admitted that might me true.

Mom set up a meeting between me and Sally a few days later and we apologized to each other for our actions. Since then, Sally has been more open with me about what she shares with Mom. Granted, she will say ‘Your mom knows what I had to say about... ‘ on occasion and prompt me to give my point of view of a certain session or part of a session to Mom.”

“Did Sally ever admit why she gave in so relatively easy?” I asked.

“Several months later Sally told me that the look I had on my face that morning was what convinced her to admit that she had been letting Mom know about everything we had been doing. She was worried I might try to do something stupid if she wasn’t honest,” Rose finished.

“Part of the reason we shared those stories with you is to make things a little easier for the two of you. In both of our cases, our mentors tried keeping secret the level of communication they had with our parents. As a result, Rose, and I both got worried, wondering ‘what would our parents’ reaction be when they find out what we had done with our mentors,’ especially considering that the mentors were good friends of theirs.” Jessica commented.

“It’s funny now to look back at things knowing a more complete story than we did back then. As it turned out, both Jessica and I initially thought that our sex mentors had self-selected themselves – without our parents knowing about us having them as sex mentors,” Rose said.

“We were half right. As Rose and I would learn later on, our sex mentors had volunteered for the job. It’s just that they functioned with our parent’s knowledge and approval, instead of trying to keep things hidden from them as we initially feared.” Jessica mentioned.

“Some of the biggest differences between our experiences was that I confronted my mentor and was ready to tell them goodbye forever shortly after my worries started. At that point, unlike Jessica, I had also overheard much of one side of my mentor revealing details of the sex I had with her and Art, which I also revealed to her. I found out a few weeks later that Sally had informed my parents of our pre-breakfast confrontation while I waking Art up. She also told them that I knew that they approved of Sally and Art being my sex mentors.” Rose added.

“In contrast, I spent several months worrying about what would happen to me, and admittedly to a much lesser extent, to Bob and Lucy, if our parents learned of me being sexually active with them. Prior to that pivotal confrontation with Lucy, I had some suspicions, but no proof she was keeping our moms, and through them, our dads, updated on the ‘progress’ of my sexual education. To illustrate the change since that day, as far as I know, Lucy has never come out and admitted to our moms that I know she has kept them updated on that subject since the beginning.” Jessica added.

“If I am understanding things correctly Lucy seemed determined to keep the fact she had been keeping our parents updated a secret for a while. Then on the day of your final confrontation on that subject, she seemed to have changed her mind real fast. Did something happen that made her more likely to change her mind?” I asked.

“What about the large difference in resisting to reveal that secret in Sally’s case where she put up very little resistance to Rose’s questioning?” Tom asked.

“Both sets of mentors knew a family that had a girl that I will call Julia who was between Rose’s and my age. Like Rose and me, Julia had started being mentored in sex by a couple of her parents’ friends. At one point she wondered what her parents knew about their activities. When she couldn’t get a straight answer from her mentors and fearing her parents’ reaction, she told her mentors ‘goodbye forever.’ A few days later she was found dead after having committed suicide,” Jessica added with tears in her eyes.

“When did this happen?” Tom asked.

“Lucy found out about the suicide about a week or ten days before my meltdown on her porch. What made things worse that day for her was that the previous day she found out that Julia had left a suicide note. While Lucy had not seen the entire contents of that note, she did learn that Julia had made several harsh accusations against her parents and her mentors, giving examples in each case.”

Pausing to blow her nose, Jessica continued, “When Lucy found out about part of the contents of the suicide note, she also got either the mentor’s or a parent’s version the incidents Julia cited. As it turned out, some of the events that had triggered Julia were similar to some I had experienced with Bob and Lucy.”

“By the way, we will try to be as open as we can be with the two of you. There are some things we have promised not to talk about outside a specific group of people without permission. We will tell you that we can’t speak about a certain subject if a question on that comes up. We also will be honest if you ask us about something that we don’t know,” Rose continued.

“One example is our use of fake names for our mentors. We talked to our mentors, and they allowed us to tell you about those incidents we told you about and things we learned while being mentored. For now, at least, they prefer we not mention their names.” Jessica added.

“Part of the reason for our openness is that we have seen how much smoother our mentorship has gone after our respective breakdowns, and the changes that occurred because of those breakdowns,” Rose finished.

“Are those stories and the concerns you had the only reason the two of you came in here tonight?” I asked.

“No, that is just the first part. I know that you have not been on dates yet. Have either of you two guys done anything sexual with a girl, or another guy if you swing that way, before this morning?” my sister asked.

“So far, not counting this morning, I haven’t done anything sexual with guys or girls. My personal preference and fantasies are centered only around girls,” I replied.

“Like Robin, my sexual fantasies are centered around girls. Besides this morning, I haven’t done anything sexual yet with another person. Unless ... you want to count that time the four of us played doctor – eight or nine years ago?” Tom replied after a few minutes.

“I also can remember us getting naked to play doctor and staring at each other, but not much beyond that. Why are you asking about our experience?” I asked.

“We were asking about your prior experiences so we would know where to start. Based on your experiences, we should start by kissing,” Jessica replied.

Jessica and Rose then demonstrated how to kiss romantically. First by kissing each other, then by kissing Tom, and me. Initially Rose partnered with me, while Jessica kissed Tom, then the two swapped. I felt a little uneasy kissing my sister, who, when she noticed my discomfort suggested, “Think of this as practice for kissing Angie Muller. I don’t want to have to kick your ass for being a bad kisser.”

That suggestion helped me the rest of the night every time I was with Jessica. I did notice that Tom and neither of the girls seemed to be uncomfortable with any of their pairings. By the end of the night I was a lot more comfortable doing something sexual with Jessica than I had been at the start.

After a few minutes of practice with regular romantic kisses, Rose and Jessica started teaching Tom and I about french kisses. Again, they first demonstrated with each other and then had Tom and me practice with each of them in the same order as before.

“I think it might be a good time to play doctor again.” Rose continued with a slight blush, after we had practiced french kissing for a bit. She then stood up and removed her top, intentionally exposing her teenaged tits to Tom and me.

Jessica stood up and did the same. She upped the ante by shaking her chest after it was uncovered, “Since you are seeing us bare chested, we would like for the two of you to take off your shirts now as well.”

Our shirts soon joined the girls tops on the floor.

“Now these things have two purposes, fun and practical. I am sure all our parents would prefer we concentrate on the fun aspects for now.” Rose playfully said while holding her tits.

“Even those these get a lot of attention you normally don’t want to start things by paying attention to them. For me, unless I am already in the mood for sex, someone brushing their fingers gently along the nape of my neck is more of a turn-on, than for someone to start to groping my boobs,” Jessica continued as she demonstrated what she meant using Rose as a model.

“Staying in the same general area, for me I can get turned on by someone running their hand through my hair. Once I actually came when a hairdresser was washing my hair since I was slightly turned on before she started,” Rose stated as she demonstrated on Jessica.

Rose then demonstrated applying some gentle kisses to the collarbone before saying, “Now it’s your turn to try these things.

As I tried to imitate what they had shown me, Rose who was my first partner of the night softly gave me suggestions. After what seemed to be only a minute or so but was later told it had been ten, an alarm went off. Rose then went over to Tom’s bed and joined him while Jessica came over to me. I will admit still feeling awkward with Jessica the as we practiced making out like this. Seeing and feeling her react to the attention I was giving her helped me overcome that discomfort.