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Best Friends and Lovers
By RogerGirl

June 10th:

It has been several years since my best friends and I dressed up as girls for Halloween and ended up sleeping with each other.  As enjoyable as the experience was, however, neither of us ever bring it up for fear of any awkwardness it would bring.  In case your wondering, since that experience I have been with several women and was even married for a while.  Unfortunately my marriage didn't work out and since then it's mostly been a string of one night stands.  As a guy in his mid-20s I don't really care.  The bachelor life is fine for me and after rushing into marriage so quickly in the past, I'm in no hurry to get married again.

 My life consists primarily of work, going out to the bar with a few friends from the office, and picking up a bunch of random chicks.  Other than that, I'm mostly at home alone in my two bedroom apartment.  Why the two bedrooms you be wondering?  Well, I had originally moved into the apartment with my ex-wife with the hopes of starting a family.  Those plans fell through, however, when I caught her cheating on me with her co-worker Spencer.  It's strange though, I'd always thought Spencer was gay.  I found out just how wrong I was though when I came home one day to find the two of them in bed together.  

 No more, man.  I'm definitely not done with chicks, but I'm done with the whole relationship thing.  Being in a relationship is a lot of work and frankly more stress than it's all worth.  All I need from a woman is sex anyway.  Sure it might get a little lonely being in this big apartment all alone, but the freedom is worth it.  Take a look at me right now.  I'm sitting on the couch in my boxers watching football and drinking beer.  The apartment is a mess and I haven't been outside all weekend.  Does this bother me?  No way.  This is the dream.  Oh hey, I think there's someone at the door.

"Hey, Mike,"

"Hey, Steve.  Sandra threw me out.  You mind if I crash here for a while?"

"Sure, bro.  The spare room is yours.  You want a beer?"

"Thanks man."

 It looks like my buddy Mike here is about to find out how much better the single life is.  I've seen how whipped he was with Sandra.  Trust me, this is the best thing for him right now.  Sure he looks like a mess right now, but that'll all change in a week.  After I take him out to pick up a few chicks, he'll forget Sandra ever existed.  

June 21st:

 Well, it's been a couple weeks or so since Mike has moved in here and he's still moping around the place.  He has no job and hasn't sent out any applications to find a new one.  He hasn't shaved or showered in days and he just stays in his room day in and day out.  I've tried taking him out to pick up chicks, but he just sits alone at the bar and mopes.  I really need to get him out of his funk.  It's ruining my chances with the ladies.  I haven't been able to bring a girl home since he's moved in and I really need a release.  I know he's dealing with a bad break up and that he's my best friend, but it's really cramping my style.  

July 16th:

 It has been weeks since I've had sex and it's driving me crazy.  I fear I'm starting to have strange thoughts about Mike.  His hair has grown pretty long and he's lost some weight since he hasn't been eating much.  Yesterday, I accidentally walked in on him naked and I swear he looked like a chick.  Sure he has no boobs and he has a cock, but he definitely has the body of a girl.  I also found out that he took some of Sandra's clothes and underwear with him and he often cries himself to sleep while holding her stuff.  I don't know if he ever wears the stuff, but I need to stop thinking about Mike and find a chick.  

August 10th:

 I stare at Mike as I open the door.  I got off early today and I guess Mike didn't expect me home for a while.  He is staring at me with a frightened look on his face.  

"It's not what it looks like, Steve."

 Mike runs off to his room and locks the door.  Well, I don't know what it was, but it looked like he was dressed like a chick.  His body was completely hairless, he had makeup on, and he was wearing a dress and heels.  Sure he had no boobs and there was a bulge in his panties, but he looked like a chick nonetheless.  Is this what he does when I am at work?  Oh, he's coming back.  It looks like he's taken everything off.

"Can we just forget the whole thing."

"Sure buddy."

September 14th:

 Mike confided in me that he's been dressing up in his ex-wife's clothes for a while.  I told him it was OK and since then he's been dressing as a chick all the time.  He's even gotten more clothes, shoes, makeup, and underwear and bought a set of realistic breasts and a fake vagina.  It turns out his wife through him out because she caught him wearing his clothes.  I guess that slumber party wasn't the last time he dressed as a chick.  It turned out he really liked being a girl.

 I don't mind Mike cross-dressing, but it can be very distracting at times.  I often find myself thinking sexual thoughts about him when I see him walking around the apartment in his short skirts and panties.  Oh god, why does he have to look so hot as a girl?  It would be so much easier if he made an ugly chick.  

October 9th:

 Mike is driving me crazy.  He's gotten rid of all his male clothing and now dresses as a girl full-time.  Also, he refuses to answer to anything other than Michelle.  On the plus side, Michelle no longer mopes around and when I come home the apartment is clean and fresh smelling.  Our relationship has become something of that between a husband and wife.  While I'm at work, Michelle goes to the market and runs errands.  When I get home there is always a hot meal waiting for me and in the morning she has a lunch packed for me.  She also does all my laundry and washes all the dishes.  

 Since Mike stayed in the apartment for weeks, my neighbors never saw Michelle as a man and they all think she is my new girlfriend.  I go along with it since it would be too weird to tell them Michelle is my cross-dressing male friend.  To be honest, I don't really mind people thinking Michelle is my girlfriend.  She is gorgeous and a lot better wife than my ex.  The only downside is she is still a guy.  I know we slept together that night, but I'd feel strange doing anything like that ever again.

November 3rd:

 Well it finally happened.  I kissed Michelle.  Last night after dinner Michelle came on to me while we were watching TV.  It wasn't the first time she has done this, but it's the first time I have taken the bait.  Since Mike became Michelle full-time, it's been hard picking up women.  How do you bring a girl back to your apartment and explain the hot chick dancing around in her underwear in the kitchen?  The answer is you can't.  Believe me, I've tried.  Even the sister excuse didn't work.  

 Well last night, Michelle was prancing around the apartment in her bra and thong teasing me like always.  I should also tell you that she's been on hormones for a while now and her body has gotten even more feminine.  When she snuggled up against me on the couch, I could resist no longer.  I grabbed her and kissed her right on the lips.  Her body felt amazing against mine and she wanted to take it a lot further.  I quickly snapped back to my senses, however, and locked myself in my bedroom the rest of the night.  

January 12th:

 Michelle and I are officially a couple.  Sorry I haven't updated you in a while, but I've been so busy with Michelle these past few months.  We've been dating since late November and Michelle's body grows more and more feminine each day.  It is hard to even remember that she was once my buddy Mike.  

 If you're wondering, we have sex almost everyday and it's amazing.  I don't know why I waited so long to give in.  Who needs one night stands when you have a girl like Michelle waiting for you at home.  I should also tell you that we also sleep in the same bed now and she's moved all her stuff into our bedroom.  To be honest, I really don't miss being single.  

March 3rd:

 Oh god.  She's driving me crazy.  I haven't had sex in weeks and I don't know how much longer I can hold out.  A few weeks ago, Michelle asked me to remove my body hair and I refused.  Since then she's refused to let me anywhere near her and went back to her old bedroom.  The house is a mess and I've been forced to order take out every night.  I have to stay strong though.  I can't give in.

April 10th:

 Well, I gave in.  After holding out for several weeks, I finally relented and now my body is completely smooth and hairless.  Since giving in, however, Michelle has been using her power over me to force me to do other things.  Last night, she forced me to wear her underwear and I did.  She's been forcing me to diet, exercise, and eat healthy and my body is almost as thin and feminine as hers.  I need to end this before I let things go too far.

June 7th:

 Well, I let things go too far.  The past few days I've been letting Michelle dress me as Stephanie as soon as I get home from work.  Each night I've been forced to walk around the apartment wearing short skirts and dresses, full makeup, a wig, and heels.  Michelle reassures me she isn't trying to change me into a woman completely and that she still wants me to be the man in the relationship.  She promises she will never force me to become Stephanie in public, but at home I will be her lesbian girlfriend.  

November 21st:

 I guess I'm living two lives now.  At work and when I go out, I'm just a regular guy.  Of course I am forced to wear pants all the time to hide my hairless legs.  Home is a different story.  The second I walk in the door, I am forced to change into Stephanie.  Now that she has breasts and a vagina of her own, I have to wear her prosthetics.  She makes me help out around the house and dress as sexy as possible.  We even sleep together as girlfriends and only have lesbian sex.  She recently told me that she was never attracted to me as a man and that it was all a game to transform me into Stephanie.    
In this follow-up to "The Slumber Party," Steve is now living alone after getting divorced.  One day his old friend Mike comes to him asking for a place to crash after his wife through him out.  What is supposed to be only temporary soon becomes long term as Michelle begins to re-emerge.  
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Submitted on
January 22, 2014
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