DEAR PLAYBOY AUTHOR BOY

INTRODUCTION

 

I got this letter from an old, old friend who is perhaps the most sexual female I’d ever met.  After a good relationship with Cable Boy ended, she found love again in the arms of Carnival Boy.  She disappeared to the west coast for a while, and when she returned, she wrote me this.

 

 

Dear Playboy Author Boy,

 

My boyfriend, Carnival Boy, is so sweet.  When I returned to the east coast, he picked me up from the airport, gave me such a big hug and long kiss, told me that it was good to have me home and that he missed me a lot while I was gone. We talked several times a day while I was gone.  That night he stayed at my place. I had bought some lube and was playing in his ass and then told him I need his cock in my ass. Oh my god,  he gave me such a tremendous ass pounding, incredibly  explosive instant  orgasm as soon as he got in there and then the ultimate was an even bigger one when  we both came at the same time.  He had such a big smile on his face, it was precious.  The next morning he still had that big smile.  He has become used to waking up with me beside him. It was only the second time he has been in my ass , but now I plan on guiding him in there whenever I want.

 

So,  you may ask,  what is the slight problem ?   Do you remember that between-boyfriends time when I had a short affair with a guy I called Mechanic Boy?  While I was gone, Mechanic Boy had been IM'ing me. He is still with his girlfriend and his sex life is still ordinary. She has not developed any new skills, will not play with his ass, will not take his cock in her ass and is basically what you would call " a good Catholic girl."

 

He said he is haunted by the passion we had together and how sexually free I was with him and that he will never have another lover like me. We had phone sex while I was in Oregon, and I swear to God the man yelled so loud when he came, his neighbors must have heard him. Now he's dying to get together again, for sex,  to the point of begging. My problem is I am still also  haunted by the monumental level of passion we had. We were only together 3 times,  but each time it was more intense than the previous time.  He holds the record of making me cum 8 times in one night.  

 

I told him that if we did,  our lives would be forever changed. He is like this terrible heroin addiction.  Once you've had it , ( I never have by the way ) you will always remember how great it was and will always want it again. He said he was the same way. He thinks about our times when he jerks off at night. He thinks about my ass and the BJ's when he is fucking his girlfriend. He called me at work yesterday and was playing with himself, telling me all the things he wanted to do to me, while I was at my desk, trying to work. God, it was such a rush - me the Midnight Virgin,  trying to sound business like on the phone while he was jerking off on the other end. Talk about torture.  See ,  one reason I want his cock so bad, is that he knows , really knows how to use it , and knows how to give me orgasms just with kissing. Kissing is so important in good sex. It warms up the body, ignites the flames and gets everything tingly while working up to the even better stuff. He found every single erotic part on my body in a flash. He hit parts inside of me that gave me instant orgasms - places no one has ever reached before or since. And somehow, I don’t think anyone else ever will, either. The instant sexual chemistry we had was way off the charts.

 

So, Playboy Author Boy,  here is a good one for your advice blog. Once you have had such a powerfully, all consuming sexually explosive relationship with a man ( who by the way has a really great big cock ) , how do you block those feelings  when you have met another man who is also a good lover,  a caring, tender man, gives you want you need and want and loves and appreciates what I  give him  in return. I don’t think I love Carnival Boy  yet ,  I care for him a lot, and like him a lot, but am still holding back on the love feelings because of past hurts. But at the same time, I think it could easily develop into love as we spend more time together. I also think our sex life will improve a lot as I show him more of what I like and he feels more comfortable about telling me what he likes. It doesn’t seem that easy for him to talk to me about sex,  but he is opening up more. Maybe he is just not used to a woman who is so open about it.

 

Help me, Playboy Author Boy!

 

Love,

Shopping Girl

 

 

Dear Shopping Girl,

 

Slight problem, all right.

 

Thisanswer assumes you are not looking for a threesome!  Because with that, you get the best of all worlds!  So here is my advice for the monogamous one I believe you to be.

 

On the one hand, a relationship that is working is not to be messed with.

 

On the other, if the relationship were working, Mechanic Boy wouldn't even enter your mind.

 

Then again, if Mechanic Boy had the balls to walk away from his girlfriend and be with you, I'd side with him.

 

But then again roman numeral two, Carnival Boy is in love with you.

 

So here's what I would do:

 

1. Make Mechanic Boy an offer.  If he dumpshis girlfriend completely and lets her stay dumped for one (1) week, you agree to date him, no promises, for up to three weeks, for a sex-only thing on the side.  This would be interesting because he had this choice before and did not choose you.  The best sex on earth is nothing if the man doesn't want you enough to dump a girlfriend for you.  Note, I am betting that this whole thing ends up with him regretfully saying no, he'll stay with Catholic Girl (who probably pays the bills).  Then, let it die.  Any further contact with him will just torture you sexually and emotionally.

 

2. In the unlikely event that Mechanic Boy goes for the offer, enforce it to make sure it's valid.  You need proof she's been dumped (like a nasty letter from her to him saying FUCK YOU, ASSHOLE!!!).  Then fuck him, and then evaluate.  Odds are, he's nothing in person like you remember him.  The emotional component is 80% of this, big cock or not.  But say he gives you great sex and he's willing to be in a relationship with you.  Go to 3.

 

3.  Now you'd have to dump Carnival Boy.  If you get to this point, consult me.  I know how this is best and most humanely done.

 

4.  Say that Mechanic Boy accepts the offer but is either unwilling to be in a continuing relationship with you or the sex isn't that great.  I'd go back to Carnival Boy and see how you feel.  Can you forget Mechanic Boy or is he still on your mind all the time?

 

5.  If Mechanic Boy rejects the offer, now you're back with Carnival Boy but you'll find that you have less chemistry for him and the relationship is on the decline.  Go to 3 above.

 

6.  The entire Mechanic Boy thing is your subconscious making a cell phone call to your conscious mind telling you that you want out of Carnival Boy.  Mechanic Boy is just the catalyst.  When you've executed 3 above, you'll find that Mechanic Boy is just kind of like old porn, you remember how it used to get you off but it's more boring than a 1940s cartoon now.

 

7.  Back on the market, wiser and more fully human.

 

Be bad,

Playboy Author Boy