Dear Debby - Issue 05

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Letters to relationship advice columnist Debby D.
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2.09
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Part 5 of the 5 part series

Updated 05/16/2024
Created 07/16/2023
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DEAR DEBBY, ISSUE 5

Dear Debby,

My boyfriend wants to marry me. And I want to marry him too.

Most of the time.

But not "all" the time, and it's that other time that's the problem.

You see, every Friday night, I go out clubbing with my girlfriends and I become a whole other woman. I let all these hot black guys dance with me and kiss me. And usually, I end up fucking them. Not always. But most of the time.

So, six days of the week, I want to marry my sweet white boyfriend. But one night of the week, I'm a slut for big black cock and want nothing to do with my loser boyfriend's white dick.

What can I do?? I don't want to sacrifice my life six days a week just for the sake of my life Friday. But I don't want to sacrifice my life Friday just for the sake of my life the rest of the week, either!

Sincerely,

Split-Personality Girlfriend.

---

Dear Split,

The first rule of relationships is: honesty, honesty, honesty! Let your boyfriend know your dilemma.

The good news is, he probably already knows what you're up to every Friday night. The fact he wants to marry you means he accepts it. So marry him and become his wife six nights a week. Let him know that one night a week, you'll stay single and available for all those beautiful black guys and their big black cocks. Best of all, with a loving caring husband providing for you six days a week, you can go "unprotected" on Fridays. If it's hot right now, think how much hotter it will be when you ditch the birth-control pill and the condom. As a married girl six days a week, you won't have to worry about becoming a single mother. You can let those superior black bulls breed you like you know you want. And then hubby will raise your baby!

Love, Debby.

**********************

Dear Debby,

Can money be a curse? I landed a job making more than I ever imagined. And now I'm worried it's the worst thing that ever happened to me.

See, both me and my high-school-sweetheart wife were poor all our lives. And because we were so poor, she was always very plain-looking. But when we were suddenly swimming in money, she started learning about fashion and makeup. She even got plastic surgery.

I was elated at first, suddenly having a bombshell wife. The problem is, she suddenly got attention from other guys too, guys who never looked at Mrs "Plain Jane". Athletic guys, player guys, gangster guys. And since she was never one of the 'popular girls' at school, she didn't have any "natural immunity". So she was a super easy lay for all of them, despite being my wife.

We just found out she's pregnant by this minor-league professional athlete she met at the club. He's black, so there's no use pretending the baby's mine. And rather than slow down, she's escalating things even further. She's made an appointment to get some body piercings and she says she intends to become MORE slutty, not less. What should I do, Debby???

Sincerely,

New Money.

---

Dear Money,

Congratulations on "making it"! You're feeling growing pains because you're not used to your new lifestyle.

Most rich guys' wives are more discreet. Their black lovers come over to their mansions instead of meeting in clubs. It will take you and your Mrs time to get calibrated.

Eventually the 'new money' effect will wear off and she'll settle down to a handful of regular black bulls, instead of the whole club every night. Is there some way to speed up this learning process? You could speed it up by helping her to associate with other well-to-do women like her. She grew up poor so her friend-circle right now consists of white-trash trailer-park types. So of course she's gonna go out and get fucked in the club bathroom like a cheap tramp. Get her associating with your wealthy coworkers' wives and she'll change. She'll turn her nose up to her old white-trash friends and she'll start getting her kicks discreetly with your black landscapers, your black chauffeur, etc.

Her new friends will also teach her the proper ways to deal with a black pregnancy. The two of you will go on a several-months' Carribean vacation (to hide her belly) and come back home with a lovely healthy "adopted" newborn black baby. I know it all seems scary and new right now, but that's because you're New Money. You'll get the hang of it, I promise!

Love,

Debby.

**********************

Dear Debby,

I have a unique condition. When a guy is inside me, my breasts swell up according to the size of his penis. The bigger his dick, the bigger it makes my breasts grow.

I used to sleep around before I got married. I would seek out the best-hung guys I could find, just to see how big my breasts could get. The biggest I ever found was this 14-inch black guy. Oh. My. God. When he forced that BBC in me, my breasts got big like watermelons! He was in Heaven, sucking on my distended nipples, rubbing his face on my enormous areolas. Fuck it made me cum sooooo good.

I stopped sleeping around after marrying. I thought that size-queen stuff was out of my system. I thought I could be content with my husband's modest dicky. He loves how his thingy makes my breasts swell up a couple centimeters.

But the more time passes, the more I miss feeling my breasts swell up REAL big. Sometimes when hubby's at work I'll just sit around all day playing with my nipples. Daydreaming about having sex with REAL men so my tits will blow up like they used to. I don't want to cheat on Darling. I really love him. But I'm starting to feel desperate!

Sincerely,

Breast Enlargement Girl.

---

Dear Enlargement,

Your condition affects about 1 in 10,000 women in America. Most don't realize it because they either don't have sex, or they only have sex with worthless pencil-dick losers like your husband.

Normally our behavior is bound by social mores. But fortunately you have an excuse. It's ok for you to cheat on your husband because you NEED to do it to properly exercise your breasts. If you don't, there's a risk you'll suffer from what experts call "small breast depression".

So as your relationship counselor, I officially condone your desire to cheat on your husband. Do it, and do it with the biggest, best-hung lovers you can get your hands on. The very BIGGEST cocks are always black, so get yourself some black loving. Also there are other factors that influence how big your breasts grow. If the guy is bareback, it effectively adds about three inches to his size, as far as the breast-swelling property goes. And if you're fertile and off birth control, that adds another three inches. So find some huge-cock BBC and basically let him breed you.

It doesn't count as cheating, as this is a medical condition and you need to do it to prevent "small breast depression". Don't worry about your husband if your black lover knocks you up. He'll quickly accept his new role as cuck provider, it's already ingrained in him from birth. It's ingrained in the subconscious of every pencil-dick whiteboy, the result of millions of years of evolution with alpha males and beta males. So there is nothing for you to worry about. Go out and get those beautiful breasts blown up like balloons, girl!

Love,

Debby.

**********************

Dear Debby,

We have three lovely kids. The two oldest are white, the youngest is half black. My wife insists she's never cheated on me. She swears she must have gotten pregnant from swimming in the public pool. Sometimes black guys swim there, and one of them must have got some sperm in the water. The problem is, if our youngest could be the result of sperm in the public pool, how can I be sure I'm the father of the older two kids? Couldn't they also be from sperm in the swimming pool?

Sincerely,

Loving Father.

---

Dear Loving,

Don't worry. If your two oldest are white, there's no chance they could be from sperm in the swimming pool. Only black sperm is strong enough to survive in a chlorinated pool.

Love,

Debby.

**********************

Dear Debby,

I've been making my husband wear condoms and pull out. We didn't want any risk that he'd get me pregnant. Now that my bull has knocked me up, my husband wants to go bareback again. He says I'm already pregnant so what harm can it do now? He says he hates condoms, they limit the sensation so much, especially after my bull made my pussy so loose with that giant black cock he's been breeding me with. What should I do, Debby? Should I let my husband go bareback again?

Sincerely,

Mother-to-Be.

---

Dear Mother-to-Be,

Congratulations!! I'm so happy for you and your husband, you'll make wonderful parents! As for your question: absolutely DON'T let your husband in bareback. He'd just get used to having sex raw with you, and you'd just be torturing him when it's time to put the condoms back on in nine months. You've gotta apply some tough love, honey. If he complains, remind him how lucky he is you're letting him have sex at all. Remind him if he keeps complaining, you'll lock him out completely and he'll never get any pussy again, condom or no condom.

Love,

Debby.

**********************

Dear Debby,

I'm confused and a little worried. The other night, in a fit of passion, I let my bull cum inside unprotected. I was so scared my husband would go berserk. But to my great surprise, he wasn't angry at all. It's almost like he LIKED that I didn't make the bull use a condom. Doesn't he know if I get pregnant the baby won't look anything like him? Is this a sign my husband doesn't care about me any more or about our relationship? Does my husband not love me any more?

Sincerely,

Confused Goodwife.

---

Dear Goodwife,

I wouldn't worry if I were you. Many men are extremely turned on by the thought of their wives getting knocked up by a superior man, especially if it means the baby won't look anything like them. From what you wrote, I can say quite confidently your husband is one of these men. You should just stop using condoms altogether with your bull going forward. When he gets you pregnant with a black baby, your husband will love you more than ever.

Love,

Debby.

**********************

Dear Debby,

The wife and I finally decided it's time to start a family. Only problem is, she's got my dick locked up in a permanent chastity cage. She says that's no problem, she can 'milk' cum out of me with our vibrator and put it in her pussy manually. Is that safe though? Is there any risk of side effects?

Sincerely,

Locked Away.

---

Dear Locked,

I admire your commitment to your marriage; your wife is a lucky girl! Getting pregnant the way you describe... by milking your cum out and putting it in manually... is mostly safe and side-effect free. But, there IS one possible side-effect you should be aware of. In many cases like yours, for unknown reasons, the baby ends up coming out half-black. Scientists are still scratching their heads trying to figure out the cause of this. Perhaps mankind will never know. But the good news is, it's entirely cosmetic, there's no actual health problems or anything, just a different skin color. So go right ahead, I wish you and your wife the best of luck as future parents!

Love,

Debby.

**********************

Dear Debby,

Is it possible for an unborn baby to get a suntan?!?! That's what my wife says happened, to explain the baby's dark skin tone.

Sincerely,

First-time Dad.

---

Dear First-time,

Yes, a baby in the womb can absolutely get a suntan if the mother has lots of sun exposure. It's especially common in places like Jamaica, Dominican Republic, the Caymans, anywhere along the equator or sub-equatorial Africa. It's even possible for the tan to be permanent. If so, count your blessings, your baby will have better melanin, better sun protection, and will probably be taller and more athletic too!

Love,

Debby.

**********************

Dear Debby,

One of your older readers here. For many years, I tried to convince my wife to take a black bull. But we're both very religious, and she felt it would be sinful to cheat on me.

Unfortunately, she has passed away, so it's too late. How can I cope with the sorrow of never experiencing interracial cuckolding?

Sincerely,

Grieving Husband.

---

Dear Grieving,

I'm truly sorry for your loss.

As for your question, you'll be comforted to know that, as she was devoutly religious, your wife is now in whitegirl heaven.

Do you know what whitegirl heaven is like?

It's where whitegirls get all the big black cock you could ever dream of. She's probably having unprotected babymaking sex with some huge ripped black thug even as you read this. If you keep on believing, then someday you, too, will go to a better place. You'll go where you can watch in the corner as your wife gets bred by all those superior black angels. In short: you'll go to whiteboi heaven.

Love,

Debby.

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6 Comments
HelperzHelperz15 days ago

It's good and fun and has been that since the first one. But a way to improve might be to get one of the people who wrote in to come back with a followup so we can continue to see what happened to them. Might be a fun twist

Stormgod59Stormgod5918 days ago

This is funny. I especially liked the one where the guy says his girl got pregnant from swimming in a public pool. The idea that anyone would believe that is hilarious. Don't stop writing the comedy... Ever!

Ridiculous69Ridiculous6919 days ago

Well that was just idiotic. Seems like your columnist must only write for the. Cuck Town Herald or the Slutsville Journal. Either way it’s the same of stuff just more cleverly written.

AnonymousAnonymous19 days ago

Hilarious!

Buster2UBuster2U19 days ago

10 Big Blazing Stars, this was so funny! thanks so much for the effort. Buster2U

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