Oca 07

A Conversation With Jenny

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(An Anonymous reader thought my Conversation with Roddy was ‘boring’. So here’s another conversation to bore him. Another Anonymous guy said it wasn’t a story at all. Very discerning of him – because it wasn’t supposed to be a ‘story’ – just a chat on line. So, for him another ‘non-story’. For my other readers, I hope you enjoy reading about Jenny’s dilemma.)


My name is Jenny. No that’s not my real name. I am 42 and a bbw. I am e-mailing you for help. I have read all your stories. The thing is, my son is my every thing, but his little slut of a g/f is not good for him. Although he’s turned eighteen, he’s always been a shy young man, particularly since we lost his father, four years ago. He hasn’t got many friends that I know of. I think he needs an older women to show him how to love. To open up new worlds. I dearly want to, but don’t think he likes bb women or milfs. Can you help me please?

So Jenny

Tell me more about your son and your relationship with him. Are you close? I assume there’s just the two of you. Have you seen him masturbate? Do you discuss sex? Has he seen you naked? You say you are a BBW – how big?? Young men usually admire big boobs! Turns them on! And have you watched him with his g/f? Do you hug and cuddle? Have you felt his erection against your body?? Lots of questions, but you need to build on existing relationships if you want sex together.


Yes Sarah,

I do spy on him playing with him self. And when he is with his little slut of a g/f. I saw her making out with some boy in a parking lot, but Tom thinks she wants do some thing like that to him. Anyway, he is a very cute boy (well he is to me!) 5’7 black hair brown eyes – slim. As for me, I am 4’11 big hips and bottie. I die my hair a lot and have brown eyes. We talk openly about sex. I was the one who gave him ‘the talk’. I don’t know if he ever saw me nude. He is a real cuddle bug when we get a good movie . We do kiss on the lips but been doing that for years really. I have seen the porn he looks at. There are no older women or bbw there. So do you think you can help me?

Well Jenny

He may look at slimmer girls on porn sites, but most boys like big tits they can really get their hands into! They’re fascinated by them, particularly big lumpy nipples! Does he know that you watch him wank? If so, admire his cock if you can, and suggest you’d like to touch it.

Next time you cuddle try rubbing his bum and pressing against his groin. If you can feel an erection there, tell him how nice it is to feel it. Watching a movie together, casually put your hand on his thigh and gently caress it. If he doesn’t object, stroke his thigh more and perhaps on the inside. If he has an erection, gently touch it and say how proud he should be to have a cock like that. Be wearing a dressing gown if you can, with little on underneath … press your boobs against his arm. Kiss his ear lobes and neck. Flatter him, but don’t overdo it!


Well Sarah.

He is way to shy for me to just touch him like that, but I did find out that I can give him a erection. We go out to the pool a lot, near by where we live. I have a old one piece that I wear, and I did a little bit shopping to get a new bikini. I told him I need a man to look at them güvenilir canlı bahis siteleri all to see how they look on me. On the third one I could tell he was hard. He told me I can’t wear it outdoors. Some one may call the cops! Lol! It was a black thong bikini two sizes to small for me. The top let you see the sides of my nipples when I move and my pussy lips were hanging out the side. He had to shuffle to cover his erection.

Keep Teasing Jenny.

Find an excuse to touch his erection briefly – then say ‘Oooo – sorry … but feels good!’ Let him ‘discover’ your nipples and boobs as you lay on the sun-bed, eyes closed. he’ll be as hard as rock. Just keep encouraging him and make him know he’s no need to feel shy or embarrassed. It may take some patience and time, but I think you’ll get there – or do I mean that your son will get there – where you want him to be!!

Keep chatting about sex and things. Ask him if he likes your body, or would he rather you were slimmer. You know the sort of thing!! Good hunting!


Oh god Sarah.

He was at college today and I was looking around on his pc. No bbw but he did look up some milf porn. I feel bad about this. I do love him and I know I want him. But, although eighteen, he is so immature and shy when he get’s home. I don’t know what to do. I am so wet. God – can’t you be near me to help? I just don’t know what to do. Here’s a photo of my big bum!

Wow Jenny!

What a gorgeous bottom! And smart panties. I’d love to peel them off to reveal what’s hidden between those wonderful thighs! I’m getting wet just thinking about it! Slipping my fingers in there. Mmmmm!

I’ve thought a lot about your problem this morning. He’s probably easily embarrassed by sex. Has he led a sheltered life?? But if he’s really shy, as you say, then please don’t push things too quickly or you might lose his trust. That would be awful! You need to keep your relationship and respect in tact, tell him you love him and realise what problems teenagers have whilst growing up. Don’t tell him that you’ve been looking at his pc! I know you won’t of course! He’d be mortified if he found out that you knew about his voyeur activities! He probably masturbates watching them!

Encourage him to be open about sex, that’s a natural development to experiment and to show interest in the opposite sex – nothing to be ashamed of or embarrassed about. You were the same at his age!! Suggest that sex is enjoyable and doesn’t suddenly go away when you become a mom! (Does he know you masturbate?? He probably thinks that moms don’t do it!)

Meantime, enjoy your fantasies and get those wonderful orgasms. But take your time with yor son!! Encourage and support him! Be his friend – tell him the odd secret to show him you trust him! Do let me know how you get on!

Sarah xxxx ps My bottom is not as sexy as yours. And my boobs are rather smaller!!


I think your really sexy and I love your boobs. I think you’re a really smart woman, so, yes, he knows I masturbate. It is that what got the whole thing started. I walked in on him jacking off, and it got me so wet. We had the talk and I told him what he was doing is ok. I even told him its ok to do it all the time at home. I know I was being so bad do güvenilir illegal bahis siteleri you think we can chat?

Mmmm. Jenny.

Oh Jenny.

I LOVE your eyes! So smouldering!! And sexy. I’d love to kiss those lips and smother your face with my kisses!

But if he already knows that you masturbate and are aware that he does as well, it shouldn’t be too far then to watch each other doing it? That might lead to other things. Particularly if you tell him that when you first watched him doing it, you were so turned on it got you all wet ‘down there’. You seem open with each other, so I wonder what the obstacle is?? Mutual watching for a start – ask him if he’d like to watch you? Or if he’d like you to watch him.

I’ll send you an IM invite.

Sarah xxxx

OK Sarah.

I’ll ask him the next time I get him really hard. It don’t take a lot!

Gosh Sarah.

Please IM me. We have hit a new place as mother and son. I am so happy.

Sounds exciting Jenny.

I have added you as friend. Should be available later this am.

Sarah XXXX

I am so sorry Sarah.

I had to work today, so can’t IM till Monday. I don’t want to be away from my son for to long you see. What I wanted to tell you was, we were cuddling on the sofa, watching a film, and I asked him if he had a erection. He was so shy. His whole face turned red. He side he was sorry and started to get up. I told him to stay, that I was happy my body made him that way and I asked him if he thinks of me when he plays with himself? That it was ok if he did. He said he did.

I told him to stay there. I had something for him. I ran up to my room and got a small toy, then lay down on my bed, and called him up to me. When he got there I held it up, and just asked if he wanted to see me use it. I was so happy when he said ‘yes’ – and so wet I came way to fast, but he loved it. I asked if I could see him do it, so he did let me but he kept his eyes closed the whole time. You don’t know how difficult it was, not to start sucking him off. I was going to, but as I leaned in to his cock, he just shot his cum all over my face. He was a little scared that I was mad at him, but I told him that I loved it. And I did!

Happy Jenny xxx


Young men of that age like to masturbate every day – sometimes twice or three times in a day. So you’re in for a feast of cum. Sucking his cock won’t be far away, believe me. Tell him how great it is to be given a blow job – tell him he’ll love it!! Then comes the first fuck!! Mmmmmm. Tell me more darling. I wasn’t sure that he’d let you watch him just yet – but YES!!!


Oh Sarah!

It gets better. On Monday, before he had to go to college, I told him any time he wanted to see me like that, he just had to ask. He is still shy but when I said I wanted to see him cum, he did ask if he could do it on my face again. I just got down on my knees and told him any time he wants. His face was so red but he did it. This time I made a show of licking all of his cum off of my face. He got hard again, so I got two shots before 8 am.

(A few days passed without any message from Jenny. Then …)

OMG Sarah.

It’s all happening! First thing he does when he gets up in güvenilir bahis şirketleri a morning, is to come into my room and jack off on me. Now any time one of us feels the need we just get off. The best part is, he seems to love cumming on my face. I am going to see if I can get him to take a bath with me today. Oh – and we always kissed on the lips, but now we start to make out when we cuddle.

Delirious Jenny. XXX

Well Jenny

What a difference a week makes!! You are now in your heaven, which you could never hope for a week ago!! I’d love to see the cum in your pussy – and his young cock!!!

So much sperm and pussy juice in and around your thighs. Mmmmmmm … no-one’s shy any more I guess!!

Sarah XXX

Oh Sarah!

Heaven! I am on my phone at the minute. He is going to take a shower now. We just got done making out, and he came on my face twice. Oh, and I’m walking around nude at home all the time now. I am so wet, it’s running down my leg. Dribbling! By now he’ll be in the tub. I’ve got to get going. With any luck I’ll show you my sons cum in my cunt. Lol!


Can’t wait Jenny.

I’d love to see the cause of your ecstasy. Let’s chat on line.


Can’t IM today Sarah.

I can only get online with my phone at the moment. Hey Sarah! I gave him his first slow blowjob last night when I got home. Gorgeous! He has a seven inch cock, but quite slender. Mmm. And the taste is divine – I’d forgotten what a turn-on it is. He came in about two minutes, but it was so hot. He has a thing about cumming on my face. He pulled out of my mouth, and shot it all over my face. Today before he had to go to college I did talk him into rubbing my clit when he sucked my nipple. I’m going to see if I can get him to eat me out when he gets home. Oh, and ya, I had sex with a guy at work today – I was just so horny I had to! He was rather surprised!

WOW Jenny!

AT WORK?? You’re getting plenty of sex now! And at work!! What a life of sex!

Later darling.

(I got an IM alert.)

‘Hi Jenny! It’s me. How are things?’

‘OMG Sarah. Haven’t got long. He’s just gone into the shower. I’m saturated with his cum!’

‘Amazing darling. Lots of orgasms for you, I’m sure. Can I have a quick feel?’

‘Ooo yes please, Sarah. I’d love you to. He’s reading a lot of mother-son stories now.’

‘Including mine I hope???!’

‘Not yet. I am going to see if I can get him to. He reads the whole slutty-mom ones from what I saw, where she fucks any thing alive. Gosh Sarah – I can feel your fingers slipping into my pussy.’

‘You are so wet Jenny. A lovely trickle of mommy juice! Warm and sticky. I want to lick it darling. Mmmm … delicious. Ooooo yeeeees. Have a quickie for me!’

‘OMG Sarah – you’re making me cum. Don’t stop … I can’t hold it back. Ooooooohhhhh! Jeees! It’s CUMMMING!! Ahhhhhhhhhhh. Oh fuck! Phew! That was wonderful.’

‘And quick! I love fucking new lady friends. I wish we had more time. Would you like to feel me?’

‘Can’t Sarah. Love to, but he’s out of the shower and coming. Later.’

‘Keep me in touch darling.’

(The next day by email.)

OMG Sarah!

BLISS! He has moved into my room now. Last night we went to bed as lovers, not mother and son. But I do want him to call me ‘mommy’ now – not ‘mom’ or ‘mother’. He seems to like it to.

A grateful and deliriously happy Jenny.

Hey Jenny!

Mission accomplished!!! For both of you. Congratulations to you both. Let me know if I can be of more help – though it seems unlikely!


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