Nathan's Journey Part 9

Get down on your knees.

Nathan knelt down.

Now crawl over here.

Nathan walked on all fours over to where Jenn was sitting on the edge of the bed with her legs spread open.

Put your face in it.

He moved forward taking in her scent before rubbing his face on her panty covered crotch.

Mmm, you like that don't you sissy?  Yes, you want to taste that pussy.  Tell me.

Yes, I want your pussy so bad.

Beg for it.

Please, may I taste your pussy?!

I suppose you can have a taste.  Jenn said as she slowly pulled her panties to the side exposing her wetness.

Nathan almost came at the sight of her pussy, but he held it together.

You may lick it.

Nathan leaned in and began licking Jenn's pussy.

Does that taste good?  You like that don't you?

Yes, tastes so good.

Nathan was still rubbing his cock as he licked.  Jenn sensed he was going to cum and she leaned back and rubbed his cock with the sole of her foot.  Nathan let out a scream as his cock pulsated, spurting it's cum on her soft foot.

Jenn held her foot against his cock while he came, then rubbed it a little after while Nathan was still coming down from the orgasm.  Then she put the top of her foot under his shrunken balls and rubbed her toes under them.

Now clean my foot.

Nathan started to get up to grab a towel but Jenn stopped him.

Where are you going?

I was gonna get a...

Clean it up!  Now!

But...

Clean that cum with your mouth!  Now!

Nathan looked at her with a pathetic face and began to lick the cum from her toes and foot.

Good gurl.  Get every drop.  You should like the taste by now.  I mean you really seemed to like the taste of Tommy's cum when you cleaned my pussy.

Nathan's Journey Part 8

In the car Jenn kept prodding Nathan about the party.

Did you have fun?  I know you did, I could tell.  I was watching you.  You liked it when the guys gave you all that attention, didn't you.

Nathan didn't answer, he was too embarrassed.

Jenn kept stroking his hair, running her fingers through it as he drove along.  She leaned over and whispered in his ear.  Did it feel good when Tommy whispered in your ear like this?

Nathan felt so confused and turned on.  It really had felt good and it was turning him on now, both because Jenn was doing it, but also because of the thought that he'd turned on Tommy.

When they got to Jenn's, she invited Nathan inside to relax a bit.  They went to Jenn's bedroom and she sat on her bed.

I know you're turned on Nathan.  I am too.  It's normal to feel hot after you get so much attention like that.  Do you feel a little high?

Jenn stood up and turned around.  Can you unzip me hun?

Nathan did as he was told, then like a doting servant carefully helped her out of her dress and hung it up neatly on a hanger.

Thank you Nathan.  Would you like to take your dress off too?

Nathan stood there, not knowing what to do.

Why don't you do a little striptease for me.  Take it off slowly.

Nathan clumsily began to strip causing Jenn to giggle at him.

You look so silly!  I love that you do what I say.  So obedient.  You can just take the dress off.

Nathan took it off and found a hanger to put it on.

Now I want you to show me how turned on you were.  Play with yourself in your bra and panties.

Nathan pulled his panties down and began to masturbate in front of Jenn again.  He took his cock in his hand and began to stroke it.

No, not like that.  Jenn scolded.

Nathan stopped, confused.  He was masturbating the wrong way?

Flatten your hand, nice and stiff like a paddle.

He held his hand flat.

Now gently rub yourself with the palm of your hand.  Slide your palm up and down.  Now when you get your finger tips gently make little circles under your clit head.

Nathan did as he was told as Jenn watched, smiling at his obedience.

Now rub your nipples through your bra.  Mmm, isn't that nice?  Slip your finger tips into your bra and gently rub your sissy titties.

Nathan was really turned on now.  The feeling of real female breasts under his fingers was such a turn on.  He loved having tits now.

Jenn walked up behind him and began running her hands over his body.  Gently sliding over his tummy and thighs.  She unhooked his bra and slipped it down over his narrow shoulders.  Then she began to fondle his breasts, gently rolling his nipples between her finger tips.

Nathan began to moan loudly at the sensations.

Does this turn you on Natalie? 

Mmm, yes, uh, feel, feels s good...

That's it, enjoy it Natalie.

Yes, enjoying so much.

Think about the party Natalie.  Think about all those guys there lusting for you.   Mmm, you made them so horny.  Doesn't that turn you on?

Why did it turn him on?  He couldn't worry about that right then, all he knew was that he was being overcome with wave after wave of pleasure.

Yes, imagine those hard cocks, all for you.  She whispered in his ear.  It's OK to be turned on, I am.  In fact my pussy is so wet right now.

Jenn went and sat on the edge of the bed and spread her legs revealing a wet spot on the crotch of her panties.

See how wet I am Natalie?  I bet you'd like to taste that pussy wouldn't you?

Nathan's Journey Part 7

Nathan did as he was told, taking the clothes and putting them on.  One thing was for sure, he did like the way the clothes Jenn picked for him fit his slender body.

Make sure you wear the cute little panties and bra too.  Jenn said.







Poor Nathan felt so confused.  Why was he so turned on wearing these clothes?  Why was he even doing what Jenn told him.  It all felt so right even though he could barely balance in his high heeled shoes.

Jenn kept encouraging him, telling Nathan how good he looked and how he'd be a sensation at the party.

The party?!  He almost forgot about that.  He couldn't go to a party dressed as a girl.

Jenn sensed his negativity and told him no one would no it was him.

Don't worry, no one will even suspect a thing.

Are you sure?

Yes, lots of guys do this sort of thing all the time and no one even knows.  Jenn lied to Nathan with her fingers crossed behind her back.  Besides, no one there even knows you.  I need a wing girl, c'mon.  All you have to do is look pretty and laugh at a few jokes.  I mean you could say no, but then those pics would have to go viral.

All right!  I'll do it.  Nathan grudgingly said.

When they got to the party Jenn introduced Nathan as Natalie, a friend from out of town.  Nathan just smiled coyly when  he met everyone.

Nathan thought he heard Tommy whisper to Jenn, Good job, a little shy, but she's a cutie. 

At first Nathan didn't know what to do, he was so nervous.  Jenn was a social butterfly, going around the room and chatting with all the guys.  She did a good job of checking up on Nathan frequently.

A few guys tried bringing him drinks, but he just shook his head no and smiled.  Then Jenn finally came over and brought him a cocktail.

Relax, at least pretend to have a good time.  You're doing great, just stay cool and relax.

Nathan sipped the drink, but after a few minutes the nervousness got to him and he downed the last half.  Jenn brought him another and he downed it as well.  He started getting tipsy and decided to just stay put on the couch.  Every time he looked around the room, there always seemed to be someone checking him out.  Maybe it was the liquor, but he started getting turned on feeling so attractive and would throw a smile out now and again.

Tommy sat next to him and smiled.  So Jenn says you're from out of town?  What are you into?

I dunno, soccer I guess.

Soccer?

Uh oh, Nathan thought, they might figure out who I am if I say that.

I mean, watching it.  My boyfriend likes to play.

Oh, who's your boyfriend, maybe we played against him.

Well, he's kinda my ex now.

Oh so you're available?!

Nathan was really digging himself into a hole.

No, I mean.  I'm not really looking for someone right now.

Oh, OK cool.  I'm gonna grab another beer, you want one?

Oh, no thank you.  Nathan said as demurely as he could.

Tommy got up and went to the other room.  Whew!  What a relief.

As the night wore on, most of the guys would stop by and chat.  The later it got the closer they kept getting to Nathan.  Tommy had leaned in at one point sniffing the body spray Jenn had sprayed on Nathan.

Mmm, you smell good.  I like that, what is it?

Think it's called strawberry rose.  Jenn let me borrow it.

Well, you should get a bottle for yourself.  Smells nice.  Tommy leaned in and Nathan felt his hot breath against his neck.  The sensation tickled and he kind of pulled away.

Where you going?  You don't have to pretend to be shy.  Tommy said, putting his arm around Nathan.  I don't bite.

Jenn suddenly showed up and grabbed Nathan's hands, pulling him up from the couch.  Bathroom break!  she said, girls only!

Nathan was still in shock, what the heck just happened, did a guy really just try to put the moves on him?  Why did he feel turned on by that?

I think maybe we'd better call it a night..."Natalie", Jenn said with a wink as they went for the front door.

Nathan's Journey Part 6

Nathan looked up at Jenn with the saddest eyes and pleaded with her.  Please don't make me.

Do it slut, or the pics go viral.

Nathan lowered his head slowly and opened his mouth.  He stuck his tongue out and stabbed the tip into a gob of cum, before recoiling quickly.

See it's not so bad is it sissy?  Now I want you to look up at me while you clean that cum.

Nathan obediently did as he was told, looking up at Jenn's beautiful smiling face as he licked his own cum from her thigh.

Isn't that a tasty treat for my sissy?  And look I can see that you REALLY like it too.

Jenn pointed at poor Nathan's cock which had begun to stiffen again.  If he wasn't already fully red faced his face would have lit up the room.

I think maybe that's enough for today Nathan.  I want you to go home now and think about today.  Think of it as the dawn of your new existence.

Nathan went home and couldn't sleep that night.  He lay there in bed feeling so confused.  Why did such a repulsive act turn him on so much.  Every time he replayed the scene his cock got hard.  He stroked himself under the sheets thinking about Jenn and how she had dominated him.  He was going to cum, but stopped short.  No, Jenn wouldn't like it if he came.

The next day, Jenn called and acted like nothing had changed at all.  He was to meet up with her and go shopping like always.  This time however, Jenn started picking out girl clothes for Nathan.  She handed him some things to try on.

I can't wear those, those are girl clothes.

Jenn started laughing.

What?!  Nathan asked, puzzled at her amusement.

What do you think you've been wearing?  Those jeans you have on, the blouse...all ladies items!

Jenn had embarrassed him again.  He stood there red faced as all the girls around them heard what Jenn said and were staring at poor Nathan.  Some took pics with their phones as they laughed and whispered to each other.  Nathan thought he heard one girl call him a sissy and someone else said something about a slut.

Jenn smirked, but then took pitty on poor Nathan and took his hand and led him from the store.

They went to the makeup store next and Jenn showed Nathan all the different makeups and what they did.  It was a nice distraction and kept Nathan's mind off of his humiliation.  Jenn kept holding up things next to Nathan's face and looking at this and that.  She filled a whole basket with items then told Nathan to go have them rung up.

They went back to Jenn's and as usual looked through all the new things.

You know what would be fun?  Jenn asked.

Nathan looked at her for the answer.

Could I use you for a model?  I want to try something out.

Sure.  Nathan replied, what could it hurt.

Here, sit down.  Jenn said patting the chair in front of her mirror.

Nathan sat down.  Jenn started gently brushing his hair.  He watched her in the mirror.  It felt so relaxing and calming.

Your hair sure is pretty Nathan.  I'm so glad you decided to grow it out.  Long hair really suits you.  Let's see if we can make a pony tail.

Jenn gathered his hair and made a neat pony tail, securing it with a band.

Now that your hair is up we can concentrate on your face without it getting in the way.

Nathan didn't know what she meant.

She opened one of her new makeup items and began applying it to Nathan's face.  This is going to even out your skin tone and hide any blemishes Nathan.

Nathan tried to fidget but Jenn just gave him a stern look and he quit.  Come on now Nathan it's just for fun.  Just between us girls.

Jenn applied one thing after another to his face.  She had turned him away from the mirror so she could have more room and he wondered if he looked like a circus clown with all that stuff on his face.

After about half an hour Jenn told him to look in the mirror.  He was astonished at what he saw.  He looked like a pretty girl!  What the heck?!  Nathan felt so confused, why did he like what he was seeing?

I hope you were paying attention because you need to know how to do this yourself.

Nathan didn't know what to say or do.  He got up to go to the bathroom to wash his face, but Jenn stopped him.

Where are you going?

To the bathroom to clean up, you're done right?

I didn't do all that work for nothing silly.  One of the guys is having a party tonight and we're going.

I can't go like this.

Oh, you're right.  That's why we got you this cute outfit today!  Now go get dressed!

To Be Continued...

Nathan's Journey Part 5

Nathan's head was spinning.  He felt overwhelmed and couldn't think straight.  What should he do?  Jenn answered that question when she reached over and grabbed his wrist and used his own hand to pat this cock.

He slowly began to rub himself through the soft silky panties.  It felt so good.  He looked over at Jenn, she was so beautiful and sexy.  He looked her up and down as he rubbed himself.

Pull your panties to the side Nathan.

He did as he was told and his cock sprang out.

Now stroke it.

Again he did as he was told and began stroking himself.

Does that feel good?  I bet it does.  You like masturbating to me?  You like the way my body looks in these panties?  Feels good to masturbate in your own panties and bra, doesn't it Nathan?

Nathan's mind was in a daze and with those words he completely lost all control shooting a thick rope of cum onto Jenn's thigh.

Oh! Jenn giggled.  I made you cum already?!  You made a big mess!

Nathan came down quick from his orgasm and suddenly reality hit him.  He was standing in Jenn's room in a bra and panties and had just masturbated in front of her and shot his cum on her leg!  His face was red from embarrassment as he thought of running away.

Aren't you going to clean up your mess Nathan?

He looked around for some tissue and started heading toward her dresser when he spotted a box.

Where are you going?  Jenn asked.

I was gonna grab the tissues.

You don't need tissue silly.  Come here.

Nathan came closer to her.

Kneel down.

He knelt between her legs, his eyes glued on her pantied crotch.

Now clean up your mess.

Nathan didn't know what to do.

Jenn grabbed his head and puled it toward her.  Nathan thought he was going to go down on Jenn's pussy, but instead she shoved his mouth on his the cum.

Lick it all up Nathan.

Nathan pulled away, but Jenn pulled back

I said lick it up!

Nathan looked up at her.  But, I don't want to do that.

I said clean up your mess!

No!

Clean it, or I'll show everyone these nice pictures!  She snickered as she held up her phone.

There were pics of Nathan in lingerie and masturbating!

Oh no!  Please don't show those!  Please!

One little press and they go viral!  She warned as she feathered her finger over the button on the screen.

Please don't!

Better start licking Nathan!  I think you'd better get used to the taste too.  I'm sure you'll come to love it!

To Be Continued....

Nathan's Journey Part 4

He couldn't believe what he was doing, but he was so turned on by Jenn,, he'd practically do anything if she asked.

He removed his shirt and looked in the mirror at his tits.  He couldn't help but feel turned on every time he saw them.

Then he removed his bottoms.

He reached for the lingerie.  It was so soft and smooth to the touch.  He was shaking a little as he slipped the panties on and realized he was hard down there, fully hard.

The material felt so good gliding over his hardness, there was no way he'd be able to get it down.  It felt so good hugging his cock, caressing it with the soft material.  Why had he not done this a long time ago?!

Then he put the bra on.  It was a lacy unpadded one with the hooks in the back.  He clumsily tried to fasten them, but couldn't do it so he turned it backwards and clasped it before slipping his weak, thin arms through the straps.

He took a look in the mirror and was shocked to see how well it all fit.

Jenn's voice sounded through the door, Well, does it fit?  Come out so I can see.

Nathan reached for the door knob, but paused.  Once he opened that door there was no going back.  Maybe she was just joking and he wasn't supposed to put on the lingerie?

Come on out, I want to see.

He closed his eyes and took a breath, then turned the knob and walked out.

Jenn's eyes were ogling him up and down and she had a huge smile on her face.

Oh my gosh, I knew they'd fit perfectly and the color matches your skin tone.  And I see you like how they feel too.  She said looking at his bulge.

You don't need to feel embarrassed, I think you look pretty.

She went to the bathroom and brought his new pants out and held them in front of his feet for him to step into them.

Nathan didn't know what to say or do, so he stepped into the pants and she pulled them up.  To his amazement the pants looked really good over the panties.

Turn around so I can see.

Nathan slowly rotated as Jenn watched.

See?  It all fits so well.  I must be a shopping genius!  Now about that bulge.

She reached for the button on the front of his jeans and undid it, then slowly unzipped his pants and pulled them down, never touching his aching cock once.

Oh look a little precum has leaked through your panties.  Guess you can't return those!

Nathan looked down, he was so embarrassed!

Nathan, do you find me attractive?

Yes, very much so.

Is that why your little thing is hard?

Um, i guess.

Do you masturbate Nathan?

What?!  Um, I uh.

Don't be afraid to tell me, you can trust me Nathan.

Nathan nodded positively.

Do you ever think about me when you do it?

His face was beet red now.

Well, do you?

He slowly nodded yes, unable to look at her face when he did so.

She chuckled, I like that, what a compliment.

She sat on the edge of her bed while Nathan continued to stand before her.

Why don't you show me how you do it?

What?!  No way, I mean...

Why not?  Please.  I never saw a guy do that before.

No way!

Come on Nathan.  Here, how about if I give you a little peek to inspire you?

Jenn slowly pulled her skirt back and spread her legs exposing the crotch of her panties.

To his shock she was wearing the exact same ones that he had on.

See, we're sisters?!  Do you like the way my panties look?  I like yours!

To be continued....