A Conversation with Cassandra

Hi.

First and foremost, I want to introduce myself. You can call me Cassandra, though that's not my real name. I'm a mother, 40 years old, and I've been reading your stories for a while now. I've been nervous for a long time coming, but I finally decided to work up the courage to write to you.

I've loved reading all the conversations you've had with other women online, especially how you helped them sort out their issues with incest and their sons. So I thought perhaps you could help me too. I'm not sure if these conversations are real or not. I would hope so, because I would really like advice from someone, and I mean advice from someone who would 'encourage' me to pursue my passions rather than go against them as a counselor would probably say.

The thing is, for about four months, I've been really attracted to my one and only son Elton. He's 18 and he's a really sweet boy. He's a very cute young man, a little on the skinny nerdy side but I love him very much.

About half a year ago though, my husband's sex drive started lacking. I don't know why but around six months ago he stopped making love to me as much as he used to. My husband became more absorbed in his work than in me. I don't remember how it happened or when, but sometime after he became a workaholic, I started masturbating by myself again. Without him to please me, I just had to do it myself. And one night, while I was rubbing myself, my thoughts switched to my dear son. I don't know why but it just happened and before I knew it, I became addicted. I was seeing Elton in a whole new way, masturbating to images of him, imagining him and I having sex.

It's gotten so bad that my husband can no longer satisfy my sexual needs. I know from your stories that most boys are supposedly feeling the same way, but Elton seems perfectly normal. He hasn't shown any sexual interest in me, or in older woman, from what I've observed. I don't know if I should try and act on my feelings for him, or if I should try and ignore them. And if I do act on my feelings for him, what'll I do if he rejects me?

I do hope you'll give me some advice.

ME: Hello Cassandra. That's a real cry for help darling. I can really understand your frustration and your growing obsession. First of all, let me say that all my conversations are true. They really took place. A bit of editing here and there, but I did have those conversations.

I'm sorry to hear that your love life has dwindled to nil. But it happens! Mine is just about once a week now, but then I'm rather older!! And I have to 'finish myself off', even so. I masturbate quite a lot. I love the feeling of contentment orgasms give me. Please, don't feel embarrassed, or 'dirty', at having these thoughts. It happens a lot. I don't have any children, but I would probably feel the same if I did. Sex is just so normal and natural a feeling.

Well, perhaps you can tell me what your relationship with your son is like. Do you confide in each other for example. Are you close. Do you hug. Has he got a girl friend? I guess he gets on the internet quite a lot. Does he watch porn, do you think? Most children do. Have you checked his recent browsing list? That would give you some idea of his sexual interests.

Do come back to me Cassandra, and I'll see if I can take you further.

CASS: Oh my gosh, Sarah, thank you for replying to me ... it means a lot to know that someone out there is willing to help. I'm glad to hear your stories are true ... I was worried.

Recently, my sex drive has been rather active. Before, I used to be 100% faithful to my husband. I didn't try to get off unless he was willing to help me out too. But he's been losing interest, and now that my own thoughts have strayed to my son, I can't stop myself. My son and I share a normal relationship, if you ask me. We've never acted sexual or anything like that before. Before last year, I'd never had the thought of seeing him in a sexual way. He's always been very nice and filial with only the occasional argument. It was my husband who gave him 'the talk', you know. I figured it was a 'boys' sort of issue so I let him handle it.

My son's only 18 and doesn't have a girlfriend yet. I've wondered if he was gay but my husband assured me he wasn't.

As for whether he watches porn ... I don't know why, but thinking about it turns me on. I imagine he has to have watched porn at some point in his life surely. I don't know if he does it regularly or not. I'll check his browser history when he goes for school later today.

In the meantime, how should I go about handling this? I've read your stories and now that I know it's true ... do you think I should try for a relationship with my son, or should I just forget it and move on? I know how wrong the first option is ... he might not be receptive to it, and I'm essentially cheating on my husband AND depriving my son the chance of getting a girlfriend and starting his own family ... but I just can't help it anymore. I really want him ... I'm masturbating to him almost every day now. Him living so close in the same house and yet not letting me have him is such a tease...which course of action should I take?

ME: Hello Cassandra. Thanks for the message. There's quite a lot for me to digest here, and I'm due out for dinner shortly, so have little time to respond straight away. However, I'll think about all you've said and get back to you, probably tomorrow. But, please don't torture yourself. You are certainly not a wicked mother!! It's a natural thing for many moms, as you've already read in my conversations. In my experience, an affair with your son will not prevent him from falling for another girl eventually. If anything does develop, I'm sure it will be an adult thing between you. More tomorrow darling. Meantime, keep your fingers busy!! Sarah xx

CASS: Hey Sarah. Sorry for being a bit of a downer in my last messages haha, I guess I was just feeling a little helpless. Well, I've thought long and hard about what you've said last night, and about my feelings, and I think I'm going to try and see if I can seduce Elton. If he recuperates my feelings, perhaps he would be open to a little fun. If he isn't, well, I'll know that at least I tried, and that I didn't let this opportunity go to waste. I do hope that he won't mind though, and that maybe in the future he'll find a girl better than me, someone suitable to his age and who will give him a good family. I want to hold his grandchildren, so with you as my witness, I hope that doing this is just to clear my head, sort out my feelings for him, and not to deprive him of the chance to start his own family some day. I don't want him to be my boyfriend or anything like that, that'd be kind of weird haha.

Anyway, I took a look at his internet history, but it was just the usual stuff, youtube and some gaming videos and typical boyish nonsense. I snooped around his room too, there weren't condoms or porn magazines or anything. He seems clean, lol. I guess that's what I love about him, his innocence. He's such an adorable boy always acting cute around me, I think that's what first initiated my masturbatory fantasies of him, imagining purging him of that childlike innocence.

It's strange, because I was never much of a sexual deviant before, but he's the main man in most of my fantasies nowadays. I see him sitting across the table during dinnertime, and he has no idea I'm fantasizing about having him shove his erect dick inside me, and fuck me over and over, have him deposit his semen into me, on me, in my mouth and pussy.

Sorry I'm getting carried away. Anyway, I decided to take action, to try and find some way to see him without clothes on. Sometimes when he's in the toilet, claiming to be taking a shit, he can take one hour to do so, though on other days he takes 10 mins. I finally figured out that he had to have been jacking off during those suspicious one-hour long sessions, haha. I never really thought about why he took so long on certain days, because I'd never thought of him in a sexual way before.

Today, when he was eating, I took his phone and searched up your stories on literotica in his internet browser. He'll probably think he found it by accident, and won't suspect me of doing anything. I'm hoping that when he sees that story in his browser, he'll read it, and perhaps I can get him to start thinking of incest, because as far as I know, he hasn't considered anything of the sort.

I also took his clothes off the rack before he stepped into the shower, so he would have to come out of the bathroom without anything on, to get some new ones from his closet. OMG he called out to me after his shower, that he needed new clothes. He asked me to go get them from his closet, and pass it to him in the bathroom, but I pretended not to hear, so he'd have to come out. So he did. I know it seems silly, but I hardly ever see him without his shirt on, at least, since he's a teenager. After he hit puberty, he seemed really shy about showing me any skin. This was one of the first times I saw him in a while, and Sarah, he's really grown! He wasn't muscular or anything, but was more on the lean skinny side. He was still quite good looking, with that cute face and tan skin of his, and he had his towel wrapped around his legs. His face was so red when he saw me staring at him, and I just tried to laugh it off. I was pretending not to look.

He's doing his homework in his room now. I managed to snap a quick pic of him in that bath towel, and now it's my turn to have an hour-long bathroom session! Any advice on how to carry on with my seduction? I want to introduce him to the idea of incest, but I've not seen any indication that he'd like anything of the sort. He doesn't hug me too often, and I've never seen his boner before, so I'm not too sure. Would love some advice, sorry for the long message hun, but I'm glad to have you helping me. Peace!

ME: Well Cassandra. That was a lovely long message. You are being very sensible, I'm glad to say, and are certainly determined to pursue your goal, but please don't do anything to embarrass Elton, or spoil your relationship. I must admit that I am rather worried that his browser history shows no sexual content. At 18, I would have expected something. So maybe he doesn't have a strong a sex drive. I suppose he must masturbate at that age, but I wonder what fantasies he has to help him cum? Let's see if he reacts to my story you left on his phone. If there is any interest shown, he may send me a message. If so, I'll let you know of course. If not, though, you need to try a different approach by starting to chat to him about girl friends - his interest in sex. Keep it light and off-hand. Perhaps explain to him that the sex urge doesn't go away after your teens! Mention the stories on Literotica which you find interesting - mine in particular. See if he shows any interest. It could be a long haul for you darling! Maybe you need a girl friend to play with in the meantime!

You told me about getting him to come out of the bathroom with no clothes ... but have you let him see YOU come out of the bathroom with no clothes? That would make him blush I suppose! But you can laugh it off, and say something like "you'll need to get used to naked ladies when you're a bit older!" Sort of thing. Maybe let him hear you masturbating - leave the bedroom door ajar. But please don't overdo it, if the poor lad's easily embarrassed.

Gosh. Let me know what develops. Meantime, maybe I could help by stroking your boobs, finger your clit with the pads of my middle finger, lubricated by your pussy juices. Flick my tongue over it even! I would so like to do that! Mmmmm. Lovely thought!

Let me know what happens.

CASS: Sarah. Thanks for the advice! Now that you mention it, it does seem odd that my son has no porn on his history. I assume he must have used incognito or something. He probably did not want me to catch the evidence of his masturbation on his computer. Anyway, I've got more exciting stories to tell you about what happened at dinner.

My husband left for a business trip, he should be gone for about two weeks, which should give me and Elton ample time to work things out. When I was serving dinner, I purposely bent down low in front of him so he could get an eyeful of my cleavage. I didn't dare check to see if he was looking, but I could feel his gaze on me, no matter how much he may have tried to look away. I decided to do as you said and give Elton a talk about sex and girlfriends. He was so shy during the whole thing, it was adorable. His face was beet red, and he wouldn't look me in the eye. Anyway, I was going to give him a glass of apple juice, but then I had an idea. I pretended to spill the glass on my front and my shirt, especially my cleavage, got all wet. I acted like it was an accident and told him I had to go change and take another bath.

And then I took my shirt off right in front of him!

OMG he looked so shocked, I don't think he was expecting that. He told me that I was only wearing my bra, and I asked him if anything was wrong. He was so shy, he just mumbled something about nothing being wrong and fled to his room. I took an extra long time in the shower getting myself clean if you know what I mean! I fingered myself so hard in the shower thinking about him.

So when I came out of the shower, I deliberately didn't put any clothes on, and pretended like I had to check on something in the kitchen. When Elton saw me butt naked OMG! I was so excited by the look in his eyes. He looked really shocked, like he couldn't figure out what the hell had gotten into me. What got me so wet in my pussy, was that he was staring at my body for a good ten seconds before he averted his eyes when he realized I was looking back at him. I tried to laugh it off like you said and told him that I was his mother and that he had to get used to naked women eventually. Haha, he couldn't even say anything he was so embarrassed, and I have to admit it was a turn on, watching him squirm.

At any rate, when he left for the bathroom, I checked his phone and you won't believe it. His internet browser showed that he was still reading your stories! Wow! The story that I'd looked up on his phone, the one about Rene, was now on the one about Debbie. He'd actually read your stories! I can't believe that this is actually working!

I'm going to leave the door slightly open tonight when I masturbate and see what happens from there. Do let me know if Elton emails you!

ME: Wow indeed! That's great Cassandra! I'm so glad he's reading my stories. It might just persuade him to ask my advice, though it may take a little time for him to pluck up some courage. I hope you have good boobs for him to admire! And a nice pussy patch! At least, you're getting some good orgasms out of it! Me too!! Do keep me in the picture! Mmmm. Love it when it starts to work out!

CASS: So before I went to bed, I told Elton that the lock on my bedroom door had broken, as an excuse for me not locking it. Then, I purposely left a small gap open in the door. God, I was dripping wet just imagining him watching me. I laid out naked on the bed and started caressing my breasts, sticking my fingers in my pussy, fantasizing about it being his dick. I heard him shut the television off, and head to his room, so I let out an extra-loud sigh to get his attention and it WORKED! Out of the corner of my eye, I saw him peeking in at me, and his eyes widened, he was swallowing hard and everything.

I don't think he knew I was watching him or he wouldn't have stayed there for so long. He probably thought I had my eyes closed, but I had them squinted slightly open to watch him.

He eventually came in, and asked me what I was doing. I acted like it was normal and I said that "Oh, honey, everyone masturbates every now and then, you know. Just cause I'm an older woman doesn't mean I don't do it. I know you masturbate too." And his face was so freaking red, he looked so embarrassed with himself that he couldn't turn away. I was so scared and unsure what to do, my heart was pounding, but I told him that masturbation was a natural thing and that he shouldn't be ashamed of doing it or seeing me do it.

He hurried back to his room afterward, and I decided to go check on him. So I sat on his bed, and just touched his thigh as I spoke to him, trying to be casual and, OMG Sarah, I could feel his hard on! It was the first time I'd felt it, ever. I think the events of today really got to him because he seemed more distracted than ever. And I was still naked when talking to him, and he could not take his eyes off me. It's so crazy, this is the first time I've ever seen him take a sexual interest in me.

Sarah, you are a MIRACLE! I'm going to continue working on him tomorrow, see when to make my next move, Do tell me if he messages you at all because I'm dying to know what he's thinking.

ME: Amazing Cassandra! That is fucking amazing! You carried it off like a professional! (Though a professional what I don't know!!) But do take it easy darling. Don't you think perhaps you could give it a break for a day - give him time to recover. After all, you have enough memories - feeling his erection for example - to keep you going for a day or so!! I just thought, perhaps, he might want a little time to digest what's happened. By all means chat with him of course, but he must be so confused with the speed of developments, he needs some time to think things through. He's only 18, after all! But, you have done a FANTASTIC job there, with motherly love and care!!

If he does send me a message, of course, I'll let you know. I do so hope he does. I can't think of any way to encourage him to though!

Wow!! And WOW again! Cock inside not too far away now! But you've waited so long, a day or two more won't harm!!

CASS: You're right Hun, I have been a little over-eager. Four months or so of sexual frustration can put me in an impatient mood. You are the master of this haha ... so I'm sure you know best. I'm going out shopping with a few of my girls tomorrow, so that ought to give my little man plenty of time by himself at home to sort things through. I'll get back to you when there are further developments.

ME: Good for you Cassandra! Perhaps you should tell him you're sorry if you caused him any embarrassment, but it's time he started to find out what makes women tick! We still need sex in our thirties as teenagers do, but we're not quite as impatient!! (Well, you are, but don't admit it!!) You want him to learn about sex safely with someone who cares for him and that you're here for him to explore. In his own time, as it were. That's what moms are for!! Can't wait for the next installment!

I haven't heard from him by the way!! Maybe he's too confused, or shy!!

ME: Hi darling. Over lunch I was thinking about you and Elton and thought, maybe, you might encourage him to explore your body as part of his sex education - what makes women tick. At an appropriate time - maybe after dinner, sitting on the sofa - you might ask him if he would like to know more about women's bodies. What they feel like, and so on. Encourage him to explore your breasts, fondle them, weigh them in the palms of his hands, suckle the nipples. Perhaps undo your top and remove your bra, offering them to his gaze and touch. Then, explain how women like to feel their tummies being stroked, saying that it feels very sexy. Then, of course, how would he like to know what a women's genitals feel like? Suggest he runs his hand between your thighs - show him the clit and explain how touching it causes women to get very aroused, etc., getting wet to make the passage of the penis nice and easy. Finally, if the time seems right, how would he like to feel what it's like to sink his penis inside a woman. Encourage him ... "go on - it's there waiting. Wanting to feel filled." Whether he fucks you, or you fuck him, depends on how this have developed of course. Then, if all goes well, you can invite him to join you in bed every morning when he wakes up, for another lesson in love.