CHAPTER ONE

 

My name is Alex Trenton, and I didn't mean for it to happen. In fact, even though I took the first step, I am not responsible. I am the victim here.

***

I was sitting at my computer, it was a Tuesday night. I had a bourbon and Coke I was sipping, and enjoying very greatly, and I was surfing porn.

I know, me bad, but Tanya, my wife, was at a convention for the week. I was all alone, and...and I was sitting there in my bathrobe, stroking my hog, getting all excited over the babes I was looking at.

Big breasts heaving, while some big-dicked stud plowed them.

Some cock tunneling between big breasts and shooting cream all over the delightful flesh.

Or, my favorite, big breasted women on all fours, jerking back and forth, facing the camera so I could see those enormous hooters and those red, red lips.

Money shot after money shot, squirting over buttocks, boobs, gorgeous faces, and I was ready to shoot my own load.

DING! The box flashed up on my screen. I had a message.

I started to delete it and stopped. It was from...Mistress Mandy?

Mistress Mandy? Who the hell was that?

I didn't recognize the name, but there was this little round picture of, get this, red lips, on the message.

I love red lips. And I know I shouldn't have done it, you're not supposed to open anything you don't know on the web, I opened it.

The message read:

I saw you the other day and knew.

You are the perfect man.

I've been stalking you.

I want you to do something for me.

 

I blinked. Stalking? Out of the blue?

I went over all the women I had met over the past few weeks.

There were women at work. There were women on the street and in stores. But who, what woman, would pick a guy out at random and stalk him?

DING!

Please do something for me.

You have to.

I'll die if you don't.

 

She'd die? What the heck?

Merely a figure of speech. No intention.

But it was powerful, made me notice, made me not delete and block.

I typed:

Who is this?

 

I sat back, sipped a bit of bourbon, and wondered.

Was it Marsha? That secretary at the office? I had flirted with her, but she knew I was married.

Or maybe some clerk at the grocery store. Maybe some young thing bagged for me, and now wanted to...'bag' me.

My thoughts and fantasies were interrupted by...

DING!

It doesn't matter.

I just know that you like porn,

and that we have the same tastes.

 

She knew my tastes? Maybe it was just a random porn advertisement, searching for a sucker.

No. There had been request for money. The internet always wants your money.

I typed:

 

What do you know about me?

 

I sure hoped some Russian hairball wasn't sitting over in Moscow, drinking vodka and chuckling and thinking, 'I got a bite!'

DING!

I know you like big titted girls getting it doggy style.

I know you're fascinated by men with breasts.

I know you look at all the sites

where men are dominated by woman.

I know you've had a deep interest

in meeting a mistress

who will take you where you want to go.

 

It was off the internet. Only somebody on the internet would know what I liked to surf.

DING!

Watch this!

 

A simple link. Did I dare click on it? What could it hurt? I wouldn't get a virus unless I clicked on something on the site, just looking at something wasn't going to hurt.

I clicked on the link.

A window opened, a title page, and I just about dropped my jaw all the way to the floor.

Mommy Compilation part four!

Casca and Ryan and...and all the other big titted mothers I had seen again and again. It was one of my favorites, but how had this 'mystery messenger', this 'Mistress Mandy,' known?

And I knew she, I hoped it was a she, was into my computer history.

And she wouldn't even have to crack my computer. All she had to do was hack into my Google history, or some other source.

I was actually sweating at this point.

DING!

I need you to do something for me.

You'll like it.

 

I'd like it? I'd like what?

I was scared, I was so mind fucked that I didn't know what to do.

I was being stalked.

But it was sex.

And I was drunk and horny.

I hadn't gotten any for a week. My wife was away.

I stared as some cock exploded the white stuff all over Casca's titties on the screen. Possibly the most perfect tits in the history of the world.

I looked down at my lap. I was stroking myself. I had stopped when the messages started, but somewhere along the road I had started stroking again. Probably when the Mommy Compilation opened up.

And I knew, it was the idea of the secret stalker. It was somebody, who I didn't know at all, sending me sexy messages.

I typed:

What do you want me to do?

 

DING!

Put on your wife's clothes.

 

What!? I typed:

You're kidding.

 

DING!

She'll have a bra. Put it on.

Do you have condoms?

 

I didn't want to answer, but I was compelled. This was getting too weird.

But it was a fantasy I had always had. Putting on a woman's clothes. I had read every entry on Literotica about cross dressers.

Just the thought was making my boner even more erect.

I looked down at my lap. There was a drop of pre-cum sliding out of the head of my cock.

I typed:

I have condoms.

 

DING!

Do it.

Now.

Please.

 

I couldn't bring myself to move.

I typed:

This is too weird.

 

DING!

I'm not asking you to cheat.

I just want you to enjoy yourself.

To do what you want to do.

Where's the harm?

 

I typed:

Who are you?

 

DING!

You'll never know if you don't

put on that bra.

Put water in the condoms.

Place the condoms in the bra.

 

I sat there. I sipped. My dick was getting harder. I was close to cumming, but I didn't want to cum. If I came I would lose my sexual urgency, and I wanted to keep it high.

I wanted to put that damned bra on.

I wanted to have tits, no matter how fake.

DING!

Please.

 

I typed:

What do you get out of it?

 

DING!

When I know that you are wearing that bra I will Jill off.

that is my reward for helping you.

 

It was a woman. She had said 'Jill off' instead of 'Jack off.'

But her reward was for helping me?

I typed:

Helping me?

 

DING!

Helping you find the truth of yourself.

Helping you give in to your secret urges.

Helping you realize that it's okay...

to be a woman.

 

I stared at the words on the screen. I felt like I was apart from my body, and there was a faint scream way back in the basement of my skull.

I had never thought about being a woman.

But seeing these words on the computer, putting that together with the things I watched on the internet, the porn I read...did I want to try it?

Did this 'phantom messenger' know something about me that I didn't know? That I needed to know?

I typed:

I'll do it.

 

Before I was out of the swivel chair my screen dinged:

HURRY!

 

Fuck! I thought. What was I doing? What would Tanya think? I knew this was definitely beyond the limits of our relationship.

But it wasn't like I was cheating. I was just...a little horny.

I'd do this, wack off, and see if I liked it.

I didn't think about what would happen if I did like it.

I walked down the hall to my bedroom. I opened my wife's drawer, then closed it. She would notice if I used something all folded and neat.

I went into the bathroom and looked in the hamper.

Bingo. A pink bra, and it looked like it was well worn, a little stretched.

I tried to put it on and couldn't. Damned thing was weird. And I couldn't reach up behind myself and fasten the clasps like I had seen Tanya do so easily.

Then I remembered. I had seen her method. I pulled it around my stomach and fastened it and then pulled it so the cups were in front and...cripes! The thing was inside out or something.

Of course. I mentally figured out the proper procedure, put the cups the right way, fastened it, pulled it around, and bingo. I was wearing her bra.

It was a little tight. She was more narrow than I. But not that tight.

And the boobs, thank God, were big. I'm one of those lucky guys that had a wife with big boobs.

I went into the bathroom and looked in a mirror.

A guy with a bra. Not sexy. But then why was my peter bouncing like a puppet on strings?

I returned to the bedroom and got out two condoms. The nozzle in the bathroom wouldn't work, so I had to walk through the house. The curtains were closed, but it felt so weird, and kinky, and my dick was really enjoying this. I actually dripped some pre-cum on the hallway floor.

The kitchen sink wouldn't work.

I went into the garage, and the laundry sink worked. I put the condoms over the nozzle and watched while they grew bigger.

How big is a boob? Especially when it is fake and about to be put into a bra like the one I was wearing?

I liked big boobs, so I let the water build up, and the condom grew bigger and hung down, and I stopped and tied it off.

I filled the other condom, trying to make sure they were the same size.

I put them in my bra.

'My' bra. Not Tanya's. In some weird way I had fashioned ownership over her lingerie.

I walked back through the house, now bouncing and jiggling.

God, it felt good, and I left more pre-cum splatters on the floor. I was really leaking now.

I looked into the mirror.

A man with boobs. Fuck!

I went back to the computer.

I typed:

I did it.

 

DING!

What's it like?

 

I typed:

Weird. Sexy.

 

DING!

Are you hard?

 

I didn't even think about how bizarre this was. I was now officially too horny to think straight.

I typed.

I'm really fucking hard.

 

DING!

Good.

Don't jack off, yet.

 

I typed.

Why not?

 

DING!

I want you to do something else.

 

I typed:

What?

 

Now I realized that I was into the game. Heysoos! What was happening to me? But I was too horny to stop.

 

DING!

Put on a blouse, or sweater, or something

that will really show your boobs off.

 

I typed:

I'll do it.

 

DING!

HURRY!

 

I got up and went back to the bedroom. I went through my wife's closet. Blouses were so thin my bra would be too visible, the fakery would be too easily seen.

Sweaters were too tight. I was afraid I would stretch them out.

A jacket? I had visions of myself, stacked, showing cleavage through the open front. But, no.

Then I saw the dress.

Fuck! A dress? The Mystery Messenger had said a shirt, but I didn't think she would complain if I put on a dress.

It was purple. Just a little loose at the neck. Stretchy. It wouldn't get all pulled out of shape.

I took it off the hanger and held it up.

Right size.

I put it on.

Oh, God! I thought I was going to cum right there! Then I realized something. I was dripping so much I was going to leave stains.

Quickly, I lifted up the dress and looked around.

Damn! What would a woman do it she had a cock that was dripping...then I laughed. A hard bark. I was imagining really strange things.

Then I figured out the solution.

Still holding my dress up I went to the hamper and pulled out undies. Panties. A match for the bra I had on.

I put the panties on, then opened a drawer under the sink and pulled out a Kotex.

I put it in the panties where my dick would drip, and pulled the panties up. I let my dress down.

'My' dress.

And realized I had gone too far. The Mystery Messenger, Mistress Mandy, 'MM' I would think of her from here on out, had only said a shirt. But now I had on a dress and panties. And...a Kotex.

Which thought made my dick surge so hard I was afraid I was going to cum in my panties.

Could the panty liner catch a load of sperm? I didn't think so.

I quickly fumbled up the dress, reached into my panties and squeezed my cock. Hard. I waited, and slowly the urge to squirt faded.

Sighing, I went to the kitchen, poured another drink, then went back to the computer.

I typed:

Couldn't find a blouse.

 

No response.

I typed:

I put on a dress.

Is that okay?

 

DING!

Wow!

Perfect.

How do you feel?

 

Truthfully, I typed:

I almost came in my panties.

 

DING!

You're wearing panties?

 

I typed:

I had to.

I was dripping.

I needed a panty liner.

 

Nothing for a while. I started the Mommy Compilation video over again.

I watched those big breasts bounce and sway as men ground into women, and I felt...proud? Happy?

I had my own set of tits!

Whoever this MM was...she had called me rightly. There was something so horny and intoxicating about wearing woman's clothes.

DING!

Lipstick.

 

My mind just sort of popped. The only thing that kept me from passing out was the fact that I was sedated by whiskey.

I typed:

What?

 

DING!

You know you want to.

 

I typed:

No.

I don't.

I can't do that.

 

DING!

I can see you in my mind's eye.

Sitting there so sexy.

Your big boobs overflowing.

I can see you with long hair,

all curled and wavy.

I can see your face,

perfectly made up.

But,

most of all,

I can see your lips.

Your red, red lips.

Does your wife have red lipstick?

Really red lipstick?

 

I didn't sip now, I gulped. I needed the liquid courage.

Putting on lipstick? That would be like the final line to cross!

That was so far out there I didn't think I could do it!

I gulped again.

 

DING!

For me?

Please?

I need to see you in my mind's eye.

I need to know your lips are sexy red.

Blow job red.

Red enough for me to kiss and kiss.

Can you imagine me kissing your red lips?

Can you?

 

I could. Oh, my God, I could. I could see my lips, round and red and waiting to be kissed.

The drinks hitting me harder.

I typed:

I'll do it.

 

DING!

HURRY!

 

I ran, actually ran, to the bedroom, to the back bathroom. I opened the medicine cabinet. Nothing there.

Then I realized I was drunk and not thinking. My wife wouldn't leave her lipstick in the medicine cabinet, especially when she had a make up table.

I went to her table, and there, sitting to the side, all by itself, almost like it wanted to be noticed, was a thin, gold tube.

I sat down and opened the tube. It wasn't the roll on stuff, but a little applicator.

I puckered my lips at the mirror and began painting.

One coat made them red. Two coats filled in the cracks. Three coats. I wanted this to be perfect.

They were. Beautiful, luscious red. A light metallic sheen to them. And they looked plumper. I looked at the tube.

 

BUXOM

Lip stain and plumper

 

Lip stain? A dull thought shot through me. What was the difference between lip stain and lipstick?

Still, nothing connected.

I stared in the mirror for a long time. My lips were larger, so that was what the plumper was. And I was so-o-o sexy.

Big boobs. Red lips.

I stood up.

I wasn't big boned, but I could use a corset or something. Still, though I was a bit angular, I was so fucking turned on I couldn't believe it.

I picked up my glass and took a sip. There was only the lightest trace of lipstick on the glass. It must have dried fast.

I went back to the computer room. I sashayed through the house. I sauntered through the rooms.

My chest swayed, and I tried to put some sway into my ass. And I got an idea. Heels.

I had often admired how my wife's ass swayed when she wore heels.

I returned to the bedroom and searched my wife's closet.

In the back, a pair of three inch stiletto heels. She never wore them anymore. They had open toes and a sling on the heel.

I put them on, and barely fit. My toes stretched the front strap, and the heel strap, but I managed to stand in them.

I was shaky, had to work to keep my balance, especially with all the liquor I had been drinking.

I stood for a long moment, just practicing standing, and I saw it. On the top shelf, in the back of the closet, was a box. My wife's wig. She hadn't worn it for ages. Had only bought it for one occasion, a bad hair cut.

I took the box down and opened it. A blonde wig. Long and curly.

I tried to remember how she had put it on, and fitted it to my head. It took a while, but I managed.

I walked out of the closet. Red lips, big tits, long hair, and my ass swaying like it was a hammock.

Fuck!

And my dick was pushing my panties out and spoiling the look of the dress.

I returned to the computer room.

MM had left another message.

Where are you?

 

I sat down and typed:

I couldn't help it.

I couldn't stop myself.

 

DING!

What did you do?

 

I typed:

I put on the lipstick, then I put on high heels.

I even put on my wife's wig.

 

DING!

Oh, God!

My pussy is throbbing!

I want to see you!

 

Even drunk, I thought, no way!

I typed:

No way!

 

DING!

Well,

take a picture for yourself.

Take a few pictures.

You're going to want to remember this always.

 

I typed:

I will.

 

DING!

I need to cum now.

 

I thought about this. In my addled state I wondered. Is jacking off at the same time cheating? Did I dare?

Of course I dare. I was drunk and horny and I needed to squirt in the worst possible way.

I typed:

Me, too.

 

DING!

We need to cum at the same time.

 

I typed:

How do we work this?

 

DING!

Stroke yourself,

at the end of one minute cum.

I will do the same.

 

The idea of cuming together, separately, was erotic, and I lifted my dress out of the way and grabbed my cock.

 

DING!

Look at your computer.

Computers have the same time.

Get your message ready,

just say 'now!'

send it when your minute changes.

When the minute changes again we cum.

 

I took a quick sip, prepared my message, and watched the digital clock on my computer.

The numbers changed. I sent the message, and began stroking.

Oh, God! It felt good, within ten seconds I was holding myself back.

I could imagine her, whoever she was, diddling her pussy. Maybe using a dildo, definitely a vibrator.

She would be playing with her tits, maybe even sucking a nipple.

I wanted to suck my own nipples.

I fondled my balls.

I stroked.

Time passed, I was on the edge...on the edge...

The number changed.

"OH...OHHHH! Oh! Oh!"

Semen spurted across the room. A long rope of sticky, white fluid. My hips locked up and I couldn't move, white heat filled my mind and everything got dim. I had never experienced such an explosive cum in my life!

Then it was done.

I sat for a minute, drained and not wanting to move, but I had to send a message.

I typed:

Was it good?

 

DING!

God!

Massive!

I'm still feeling little earthquakes inside.

 

I typed:

Thank you.

 

DING!

Talk to you later.

Don't forget to take pictures.

 

I blinked It was like a lifeline had been cut. My whole world had been invested in that messaging. And now it was...over?

I typed:

Wait!

When will we talk again?

 

No response, and the message window disappeared. She had officially cut the line.

Stunned, satisfied, mystified, I knew I had to take pictures.

I reached into a drawer and took out my good camera. No stupid cell phone for this babe.

I put it on a tripod and set it up in the living room. I used the timer and took a series of pictures. I posed. I kissed at the lens. I flaunted my its. I never felt so sexy.

And the nice thing, my bump was gone. My boner down, the dress was smooth and not showing any hint of my package.

And then, finally, it was over.

It was time to get undressed and be a man again.

Truth, after I had cum I was ready to change back. I guess that was a good thing. It meant that I just wanted the sex, I didn't want to remain a woman. which shows how people can delude themselves.

Still, I stalled just a bit longer.

I uploaded the pictures to my computer and put them in a file, and I hid the file.

I smiled. Nobody was going to find these puppies.

Then I washed my glass out, odd, the lipstick stain, as light as it was, was very stubborn. Didn't want to come off.

Then I washed a bunch of glasses. They were just sort of dusty, and I imagined myself a woman, just bopping around and doing housework.

Then I washed the cupboards off, cleaned a few more things, and realized the time.

It was two in the morning! And I had been prancing around like a woman for hours! Hunh! Maybe there was a part of me that did want to be a woman.

Then I talked myself out of it.

It was just a one time thing.

I went to the bedroom, thought about sleeping as a woman, then decided against it. I wasn't that horny anymore, though I did have an inner buzz of excitement running through me.

I took off the wig and put it away. I took off the dress and hung it up. I took the water condoms out of the bra and put them in the sink. I didn't pop them, I wanted to wear them again. I probably wouldn't, but...I just left them in the sink.

I took off my panties, and the liner was soaked from the pre cum I had emitted earlier. I smiled at the thought of how much juice I had shot. God, what a night!

Finally, I looked in the mirror at my lipstick. Lip stain. My lips were still plump. This stuff really worked.

I decided to just hop into the shower and wash the stuff off.

I turned the water on hot, hopped in and soaped up.

I rubbed my lips, soaped them good, rubbed them some more, and grinned. I would be clean now.

I got out of the shower, dried myself off, and looked in the mirror.

Oh, no! The lipstick was still there.

I grabbed a washcloth and soaped it up and scrubbed my lips some more.

They stayed red. In fact, because of all the rubbing they were a little redder.

A little worried, I went back to the computer and powered up. I researched lip stain.

Long lasting than lipstick. It doesn't just apply a color over the lips, it stains the skin.

My jaw dropped and I stared at the screen. The site I was on had dozens of red lips on it. Lips on women. Red lips where they should be. Not on a man.

What had I done?

I researched some more. Most stains came off within a day. I looked up the particular brand I had used. Three days. One day to lose most of the color, but three days to lose all the color.

Three days.

It was Wednesday night. That meant Thursday, Friday, and Tanya was due home on Saturday. Saturday afternoon.

Yes. It would work, though there might be a little redness left. but I could talk fast and cross my fingers...it was workable.

But, first, I was going to have to call in sick. I couldn't be seen at work with lips like these.

So I set my alarm and went to sleep.

And woke up late. And my head hurt.

I groaned, rolled over and picked up my cell.

There was a message on it, from Tanya.

Tried to reach you last night.

Where were you?

 

I was dressing up in your clothes, my love. Why do you ask? I giggled.

I called up work and put on my best fake cough. It was pretty easy, and they bought it. Heck, in this day of COVID the slightest wheeze was an excuse to lock down and quarantine.

I called Tanya then.

"Hey, babe! How you doing?" she greeted me.

"I'm good, but I miss you!" At least I missed you until last night, and then I was a bad boy.

"Oh, I miss you, too. I can't wait to feel your big dick in me."

"Whoa! I like that! Tell me more."

"I couldn't help myself," she giggled. I masturbated last night."

What!? She never did such things. She was the original Miss Goody Two Shoes.

"I can't believe it."

"Believe."

"Well, how was it?"

This talk was turning me on. And I was already turned on by having dressed up the night before, and by looking at my red, red lips this morning.

"Oh, I had a big bang. The kind that just sort of take your breath away and leave you dazed and confused."

"Geez, hearing you talk like that has given me a boner. I'm going to have to jack off."

"Don't you dare! You save it for me! When I get home I'm going to jump your bone seven ways from go."

"Oh, so you can beat off, but I can't?"

"No. You're a man."

"And I have a man's needs."

"You've had your needs filled too often, and you're going to get your needs really filled when I get home. So no jacking off!"

DING!

I stared at the computer screen. MM had sent me a message? Right while I was talking to my wife!

I clicked on the message box.

"Honey? Are you there?"

"Uh, yeah!" My mind was caught between two conversations, I was fumbling the ball.

On the screen:

Hi, lover.

You ready for tonight?

 

Oh, no!

"Yeah I can't wait to fuck you," I said.

"You sound kind of funny. Is everything all right?"

"Oh, yeah..."

I typed:

Yes.

 

I said: "I'm just looking forward to making love to you."

 

DING!

We're really going to go crazy tonight.

Are you ready?

 

"I'm ready," I said.

"What?"

"What?" I was getting confused.

DING!

We're going to paint your nails

and dress you all the way up.

 

"You just said you were looking forward to making love, and then you asked 'what.' What's going on?"

DING!

Then you're going to walk around.

Outside.

You're going to be so brave.

 

I tried to separate the conversations in my head. I pushed the MM aside in my mind, turned my swivel away from the screen, and said.

"Sorry honey, I just cut my finger. Paper cut."

"Are you all right?"

"Oh, yeah. No big deal. And I can't wait to see you."

DING!

I ignored the bell. "I'm going to go crazy on you."

She giggled. "That sounds like fun. But can you handle a real woman?"

As opposed to a computer message woman? "Oh, yeah. I feel like a real woman right now." I blinked. Was there something revealing about what I had said?

DING!

"Like the Shania Twain song," she said.

I searched my mind. I didn't want to read messages. Oh, yeah. I remembered the song. I hummed a bit of it.

Tanya sang: "Man, I feel like a woman."

DING!

But now I was successfully in the groove. I put aside the thoughts of the constant messages and focused on my wife.

For a long minute we talked, and even talked dirty, to each other, then it was time to hang up.

DING! DING! DING!

Her last words were, "Well, take care of yourself. You do sound a little strange."

"I'm fine. And I look forward to Sunday so much."

"Me, too. Bye, lover."

I hung up, and I was aware that MM had opened up by calling me 'lover,' and that my wife had hung up calling me 'lover.'

What a tangled web I was in.

I turned to the computer and opened looked at the messages.

 

I want you to tell me what you want.

 

I want to Jill off with you again.

 

Would you like to put on eye shadow?

 

In my mind I am kissing you right now.

 

I'm playing with my pussy, it's hot and wet for you.

 

I'll talk to you tonight.