Chapter 5: Sex Mentors – Jessica

Late the evening of March 15, 2011

Shortly after Tom and I had gotten ready to go to bed and turned off the light, I heard a soft knock on the door leading to the common room. Carefully walking to the door and cracking it open, I whispered, “Yes?”

“Could we come in for a few minutes?” Came a whisper from outside.

After I had opened the door a little wider, two figures entered the room that Tom and I were sharing.

“Is Tom asleep?” The second person asked in a low voice.

“No, I am awake,” came from his bed.

In response to that, Rose turned on the light. She then reached around me to close and lock the door. She and Jessica had changed from the shorts and t-shirts they had been wearing earlier in the evening at the birthday party. They were now dressed in semi-transparent lingerie. While not skintight, their outfit accented the curves of their nubile bodies. If anything, Rose and Jessica looked sexier now than they had when I had seen them topless earlier today.

Pushing my mouth shut while handing me the napkin she had in her hand, Rose started, “If you don’t mind, let us sit down for a bit and talk.”

Rose sat down on the side of the bed that I normally used. She then patted the bed next to her, indicating where I should sit. Across from us, Jessica sat down on Tom’s bed. Tom initially just scooted himself up to a sitting position, before getting up. He then sat down next to Jessica and across from Rose...

Once we were in place, Rose continued, “Starting tomorrow morning, Dad will want to have some talks with the four of us, revealing some more details of the family history and a few of our secrets. That is all I know about what the talks will involve.”

Jessica then added from Tom’s bed, “Before we get to why Rose and I decided to come in here tonight, we need for the two of you to promise us something.”

“What do you want for us to promise?” Tom asked.

“We need for you to keep what you learn and what might happen in here tonight a secret,” Jessica replied.

“Is it something that will get Tom or me in trouble with either our parents or grandparents?” I asked.

“My parents have given their approval for what Jessica and I have planned for tonight. In fact, they have given some suggestions. For now, the promise we would like for you to make is to not talk about tonight with anyone outside the four of us and my parents,” Rose replied.

“Will there possibly be other people who we could talk to about what Robin and I might learn?” Tom asked.

“Yes, in the future we will add some other names to the list of people you can talk about tonight. Some things, like some experiences Jessica and I have had with our sex mentors, you could talk about with them – once you find out who they are of course,” Rose replied.

“I am fairly confident that the two of you would not get in trouble with our parents for anything that you might learn or do tonight. I can’t explain to you the reason why I have that confidence because of some promises I have made. In fact, I might get into a bit of trouble just by telling you that what we have planned for tonight would likely not get in trouble with our parents,” Jessica replied.

“What do we say if our parents do ask about tonight?” Tom asked.

“If our parents ask about tonight, I don’t want either of you to lie. You can say Rose and I visited some before we went to sleep. If our parents insist on knowing what happened tonight, before Rose or I have released you from this promise, just tell them that you have made some promises not to reveal if anything, much less what, happened tonight after we came upstairs to go to bed,” Jessica replied.

“The big thing is that the two of us don’t want the two of you to gossip about what might happen tonight. Please don’t share what happens tonight to anyone outside this room, that Jessica or I don’t say it’s okay to tell,” Rose continued.

“What happens if we don’t make that promise?” Tom asked.

“Even if just one of you don’t want to make that promise tonight, we will leave both of you wondering what you missed out on as Rose and I go to bed,” Jessica replied.

I considered arguing that the one of us who made the promise should be allowed to learn their secrets. I instantly realized that they considered these secrets to big for Tom or me to resist keeping from each other for a long period of time.

“If you make this promise and then Jessica and I found out you intentionally broke it, you will find that there are some consequences,” Rose said.

“What type of consequences?” I asked.

“Basically, unless we are convinced that you have a real good reason, we would no longer trust you to either keep a secret or to keep your word. You might find others in the family would also stop trusting you as well,” Rose replied.

“Okay, you have convinced me. I promise not to tell anyone outside of this house about the secrets the two of you reveal to Tom and me tonight,” I promised.

Tom made a similar promise after having repositioned himself on his bed. “Ditto, I mean, I also promise not to reveal to anyone outside this house any secrets the two of you share with Robin and me tonight.”

“Before we go any further, I have a couple of questions for the two of you. How do you feel about incest? Specifically, brothers with their sisters, cousins, aunts with their nieces or nephews...” Rose asked.

Tom was quick to answer, “As long as there is no abuse, I am okay with the general idea of incest. Jessica had proof of that this morning...”

“Same here, although Rose was the witness in my case,” I replied.

At that point, I started to realize that tonight’s secrets would include sex, specifically, having sex with relatives. Several quick questions popped through my mind, but I decided to wait until I had a better opportunity to ask them.

“As mentioned before, Rose and I give the two of you permission to talk about tonight with Grandma and Grandpa Cunningham,” Jessica continued.

“Actually, we encourage you to talk with them about what Jessica and I will teach the two of you tonight. If you have any questions that you want an answer from the male perspective, Dad has said he will be glad to answer them,” Rose continued.

Jessica continued, “As far as I know, our parents do NOT know about what Rose and I have planned for tonight. Granted, seven other people have a general idea of what is planned for tonight. They are Grandma, Grandpa, my mentors, Rose’s mentors, and Sam. Note that each set of mentors only know that Rose or I will be sharing our story not both of them. Sam just knows of what we plan to do, not the stories we will tell you beforehand. It’s possible that one of them has revealed what they know of tonight’s plans to our parents. If they did, they would have broken a promise to Rose or me.”

Calming down a little. Jessica continued, “When our parents learn about tonight, I will probably get into a little bit of trouble with them. Not because of WHAT I will be teaching the two of you. Instead, it will be because of the timing, and because they have chosen someone else to give these lessons.”

Rose interjected, “The issue of timing would have been a lot bigger had we chosen to start the lessons before today since you are fourteen now.”

Jessica added, “As a side note, our parents don’t have anything against consensual incest in case you are wondering. I have promised not to reveal how I know that. That is not to say that the do or are willing in the future to practice the different applicable possibilities.”

“Why are you going against our parents’ wishes in this?” I asked.

“The main reason is I know our parents have planned out your future sex education. As far as I know, they want the person who they have chosen as your sex mentors to follow a plan that is similar to the one my mentors initially used with me. As far as I know, our parents think that plan is still in effect with no changes. Grandma and Grandpa started out with a similar plan for Rose.” Jessica replied.

“What is so bad about that plan?” Tom asked.

“The reason is simple, it has the potential to cause the two of you a lot of unnecessary stress. Most of the stress that Jessica and I experienced during the early days of our sex mentoring was due to secrets being kept from us. Nothing that happened between us and our mentors was kept secret from our parents. In your case, I can see your parents even trying to create conditions that would force the two of you to keep secrets from each other,” Rose answered.

“What about yesterday?” Tom asked.

“What do you mean?” Jessica replied.

“Well, yesterday Robin kept the vehicle Grandpa would be teaching me to drive a secret. The rest of the family was involved in helping him keep that secret,” Tom complained.

“Tom, yesterday it was actually Mom May who convinced me to keep the fact that Grandpa was going to teach you on a garden tractor a secret. I thought you would enjoy that prank as well. At no time was I asked to make a promise not to tell you,” I retorted.

“In comparison, Jessica and I were forced to keep secrets, even from our best friends, by our sex mentors. While I can understand the reason for some of the secrets, in other cases there was no reason at all. We initially were not even allowed to ask to be able to share some of the things we learned with others,” Rose said,

“Continuing with what Rose said ... By the time we were allowed to talk about certain subjects with some of our friends, some of those friendships had been badly damaged,” Jessica added.

“Not to give any names but someone who was one of my closest friends a year ago, has not spoken to me for eight months. It even strained my relationship with Jessica,” Rose added.

“I have imagined several consequences of our parents’ plan forcing the two of you to keep secrets from each other, none of them good. In the worst case, our family would eventually be completely torn apart, and the two of you would lose your ability to trust anyone else for a while. Even the best-case scenario I could imagine had the two of you pushing away from the family for a time. Even after your return to the family, the relationships you might have with our parents would be a lot more fragile than before,” Jessica admitted.

“Could things really get that bad?” I asked.

“Let me tell you my story. When I am done, you can decide for yourself,” Jessica explained.

“I am all ears,” I replied.

“Shortly after my fourteenth birthday, -eighteen months ago, a couple that I will call Bob and Lucy for now, who are good friends with Mom and Dad, started mentoring me. The subject was one that we don’t get at school, namely the joys of healthy sex life.” Jessica said as she started her story.

“Do Robin and I know your mentors?” Tom asked.

“Yes, the two of you know them. If all goes well, I suspect you are likely to eventually get to know Lucy the way the Bible says some men knew their wife or wives,” Jessica replied, with her first smirk in a while. “Going on with my story, initially I was just encouraged to spend time with the two of them. The first session we did anything sexual was the first time I french kissed an adult. The first adult I kissed was Lucy after she entered the bathroom while I was in it. Later during that visit, I found myself alone with Bob. He directed the conversation to the point were I asked him to teach me how to french kiss a man.”

“Over the next six weeks or so that we were together, we progressed from french kisses, to mutual masturbation, and then to oral sex. At first, I was only on the receiving end of oral sex with both of them. After a couple of times, they challenged me to guess who was eating me while wearing a blindfold. I was all for it when Bob put in a twist – my arms and legs would be loosely tied so I could not use my hands to help me figure out who was eating me.” Jessica said.

“How did you do?” Tom asked.

“I guessed wrong. Until that session Lucy had used one ‘style’ and Bob had used another one. That day they used the styles I had associated with the other one. Latter that session was the first time I gave a blowjob and ate a pussy. The second time I gave Bob a blowjob that day, was my first threesome with Lucy was eating me out at the time. My second threesome involved me eating Lucy and being eaten in turn by Bob,” Jessica added.

“Prior to that session I had only had been eaten by either Lucy or Bob, often while the other was watching,” Jessica added as an afterthought.

“Were you always with both of them in the same session?” I asked.

“No, I was only with both of them for about half of the sessions we had back then. Most of the time that I was with only one of the two, I was with Lucy. I did have a few sessions, including one that lasted about fifteen hours between the time I arrived and the time I left one Saturday, when I was alone with Bob.” Jessica replied.

“When you were alone with either Bob or Lucy, did they consider what they were doing with you to be cheating?” Tom asked.

“I asked them a similar question during the first month. My wording was along the lines, ‘Would me having sex with either of them, even if at the time it was just oral, be considered cheating, especially if only one of them was present?’ Bob explained to me that Lucy and he were swingers. They believed that as long as they were following certain rules, any sex they might have with someone besides their spouse would not be considered cheating,” Jessica replied.

Taking a small breath she continued, “Lucy then told me that in their case they had each made four lists. The first list is the second smallest of the four. I forget what she called it, but it was described as ‘tell your spouse when you have sex with someone on this list, but there is no need to ask permission beforehand.’ I am on both Bob’s and Lucy’s version of this list. Note that these lists apply only for a single session, for instance a few hours together in an afternoon or evening. Something like a weekend I spent with Bob towards the end of last Summer would require special permission from the spouse.”

“What about the other three lists?” I asked.

“The second one is ‘talk to your spouse beforehand, if you have a chance. If not talk to them as soon as you can afterwards.’ Basically, if one spouse is going to have sex with someone on this list, there should be an honest effort to ask for permission beforehand, but, if the opportunity arises and they couldn’t get in touch with their spouse, they could still take advantage of it – as long as that type of thing happens rarely. The third group is ‘no sex allowed without getting permission on a case-by-case basis.’ That list is actually the default one for those over the age of consent. As such, it applies to anyone who has not explicitly been moved to one of the other lists,” Jessica started replying.

“Do you know which list your parents are on? How about mine?” Rose interrupted.

“The only person I know for sure which list they are on is me. Bob and Lucy have told me that all the other teens they help mentor are on the first list as well, I have some guesses who might be on that list, but I don’t know for sure who they are,” Jessica replied.

“So, basically that first list could be split between permanent members and those that Bob and Lucy mentor?” Tom asked

“In practice I think it might work out that way. When Bob and Lucy were telling me of their lists, they mentioned that about a quarter of the members of the Northwick swingers group they belong to are on their first list. Everyone else that have been in the group for more than about two years are in the second group. They did mention that the two couples who have joined within the last couple of years are still on the third list,” Jessica added,

“What about here?” asked Rose.

“To be honest I am not sure how many if any of the swingers Bob and Lucy know around here are named in one of their lists. This includes Grandma and Grandpa,” Jessica answered.

Taking a breath, she continued, “The fourth list could be described along the lines of ‘don’t bother asking for permission to have sex with someone on this list – the answer is still no.’ Lucy added that there was only one person’s name on that final list. The final list also includes two groups, those under the age of fourteen, and those who are unable to give consent for whatever reason other than age. Yes this could temporarily include someone normally on one of their first three lists.”

“Changing the subject slightly,” I interrupted.

“What is it, Robin?” Rose asked.

“Do your boyfriends know and approve of your plans?” I asked.

“Phillip knows about the part that would require his permission. In fact, as he was leaving tonight, he told me to have fun,” Rose declared.

“Me teaching the two of you tonight was actually Sam’s idea,” Jessica replied.

“Could you explain that sis?” Tom asked.

“As you recall, I had a sleepover when our parents were having their ‘parents night out’ about a month ago. As often is the cane nowadays, my sleepover was with Sam at Bob and Lucy’s home. During dinner, I expressed my concerns to Sam, Lucy, and Bob without giving many details. After dinner, I was dessert in the opening round of a foursome.”

“Wouldn’t it be you had dessert?” I asked,

“No, After dunner I got undressed and lay down on the table. Bob then put some whipped cream on each tit, and my mound. He then squirted chocolate and strawberry sauce over the whipped cream. To top it off he added a cherry on top of the whipped cream over each tit and two on the whipped cream over my mound. I was fed one cherry while the other three cleaned me with their tongues. We then moved to the floor where at one point I had Bob’s cock in my pussy, Lucy using a strap-on in my ass and Sam in my mouth.” Jessica confessed.

“Sounds messy,” I replied, not knowing what else to say.

“It was. Anyway, when it was time to go to bed, Sam and I made love. It was while we were cuddling after making love, that Sam first suggested something like tonight as the first step in making sure my concerns didn’t come to pass. It was with his encouragement that I added Bob, Lucy, and our grandparents in the planning as well as Rose in carrying out the plan.” Jessica said.

After taking a breath, Jessica added, “In exchange, Sam would like to watch the two of you make love to me for some reason.”

“When did you go beyond oral sex?” Tom asked, in what he would later say was an attempt to get Jessica to return to her story.

“A couple of days after I had been given the ‘swinger’s talk’ I had one of my solo sessions with Lucy. That day, I admitted to her that I was considering giving Bob my vaginal cherry. That day she used a dildo to see if I still had a hymen, which I had apparently lost at some point. She also convinced me to wait a few days since Bob had a big birthday coming up in the next few days,” Jessica replied.

“What happened?” Tom asked.

“Lucy then called one of our moms using one hand. The other one was busy playing with my pussy. As soon as Mom picked up, Lucy asked her if I could spend a Friday night near Bob’s birthday with her and Bob. The answer was an immediate yes. The ease with which Lucy got permission for me to have a sleepover with them made me wonder exactly what Lucy had been telling our parents about the time we spent together.”

“Could you tell us about Bob’s birthday celebration?” I asked.

“When I arrived at Bob and Lucy’s home on the day we would be celebrating Bob’s birthday, Lucy answered the door and as she was taking me to her bedroom she revealed that indeed her kids were off on sleepovers of their own, “ Jessica started, as she started rubbing herself.

Closing her eyes, she continued, “Once in their suite, Lucy had me get undressed and take a quick shower. When I was done with the shower, she had me put on a real sheer short-sleeve leotard. Except for my arms, it covered me about as well as the combination of my cheerleading leotard and the shorts I wear under my cheerleading skirt.”

Laughing she added, “Granted, that leotard didn’t conceal my body anywhere close to how well the cheer leotard does. Lucy then tied two ribbons on me, one going across my nipples and the other one on my hips. Thus decorated, she had me lay down on a towel she had placed on her bed while I was in the shower. After adjusting the bows, she put the tails of the lower ribbon so it would cover my slit before she called Bob to open his present.”

Jessica then interrupted herself, “I can see you both are wondering how I was feeling while I was waiting for Lucy and Bob to return. The best way to describe was a mixture of horny, worried that my first time would hurt, and a little afraid of what our parents would think if they found out.”