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....

Nathan's Journey Part 3

When Nathan got in the bathroom, he was both excited and confused.  Excited because Jenn had left the new panty and bra set out that she'd bought at the mall.  What a turn on.  He was confused though, because he couldn't find the clothes she'd bought for him.

Um, Jenn, where's the clothes?  He asked through the door.

They're right there silly.

I'm not seeing them.  All I see is..., his voice trailed off as he was too embarrassed to mention her lingerie.

You mean the bra and panty set?  You can say it silly.  Aren't they pretty?  I could tell how much you liked them in the store, so I got them...FOR YOU.

Huh?!  Now he was really confused.

Suddenly Jen opened the door without knocking.  Nathan was in just his t shirt and pants, but he instinctively crossed his arms in front of his tits.

Jenn laughed when she saw his reaction.  What are you doing?  Uncross your arms.

No!

Why?  What are you hiding.  Did you steal my panties?

No, I just can't.

Why?!

I dunno, I just...

Don't you trust me Nathan?  I thought we were so close now.  Come on, you can show me.

She reached out and gently began uncrossing Nathan's arms.  His nipples were hard and showing through his t shirt.

Oh my, looks like someone's cold!  She snickered.  Let me see.

She ogled Nathan's tits.  I think it's cute; cute and well, sexy.

Nathan couldn't believe his ears.  His freak show body was turning Jenn on?!

Really?  You like them?!

Of course, you didn't think i hadn't noticed did you?

I dunno, I um, I....

Now I'm gonna leave you alone, put on your new things.

But there's nothing here.

Sure there is silly.  Jenn pointed at the bra and panties.  They're right there.  Now put them on like a good girl and model them for me.

To Be Continued....

Nathan's Journey Part 2

Nathan and Jenn became shopping regulars, hitting the mall a few times a week.  Nathan hoped Jenn liked him, she was so pretty.  She even brought him to the lingerie store.  He was blushing as she held up different bras and panties. 

Do you like these?

He couldn't even answer he was so embarrassed.  He nodded yes.

I can tell you think these are cute.  I'm getting them.

Nathan hoped he'd be seeing Jenn in her new lingerie at some point.  The sooner the better.

He was really excited when she suggested they go to her house to try on their new things. No way he was turning down that offer!

When they got there, no one was home.  Awesome, he thought.

They went upstairs to her room and he sat on her bed as she took the bag of clothes into the bathroom and changed.  He was so excited as he waited.  He looked around her room at her things.  He noticed her bed wasn't made and saw a cute pink babydoll nightie.  He looked toward the bathroom and the door was still closed so he grabbed the nightie and held it up.  It was pink with see through panels and lace around the breast area.  What a turn on!  He thought he heard her, so he quickly stuffed it back by her pillow.

The bathroom door opened and Jenn came out in her flirty little summer dress.  She looked super cute in it.  The bottom hem was only a few inches above her crotch and he wanted to see her panties so bad.

Well, what do you think?

Awesome Jenn, you look really good!

Thanks sweetie.  She said as she twirled around for him.  The hem rose slightly, but just enough to tease Nathan even more, never revealing her panties.

OK, your turn.

Nathan went to the bathroom to change and closed the door.

He took off his pants and shirt and was reminded of his breasts again.  Oh no, he didn't want her to see them.  She'd picked out a black button up short sleeved shirt for him, but the top button was kind of low.  Must have been one of those European type men's shirts.  He decided to wear his t shirt under it, just in case.  He put on his new pants and they fit great, he filled them perfectly.

He opened the door and Jenn couldn't stop gushing about how good he looked.  Her only criticism was about the t shirt under his shirt.  Why'd you do that? Don't wear it like that, it wasn't meant to have a t shirt under it.  Go take the t shirt off.

Nathan refused and promised he'd remember not to wear the t shirt next time.

Alright, don't forget though.

She went in the bathroom again and came out in yet another killer outfit.  Man, she really knew how to look fabulous.

Then she told Nathan to put on his next outfit.

Nathan was confused, he only bought the one set of clothes that she'd picked for him.

Surprise!  I bought you a few things, I thought would look good on you.  They're in the bathroom.

Nathan felt so special.  She must really like him, he thought.

To be continued...

Nathan's Journey

 Nathan had always been smaller than the other guys.  Try as he might, he was never as fast for agile as they were.  He just couldn't build the muscle mass that most guys could.  Still, he continued to come out and play soccer with them, determined to prove his manhood on the field.  It didn't work at all though, and the guys were well aware of it.  Because of the coach, everyone got equal playing time, and the rest of the team was paying for Nathan's weakness.  Brad, the team captain, decided to take things into his own hands and had a talk with Nathan.

Nathan, dude, you've been playing with us for two years now and you ain't making the cut bro.  I think you need to bulk up, you're too frail and weak to keep up.

I tried taking supplements and protein shakes, it's not working.

Here, try these. Brad said, handing Nathan a bag of pills.
Just take one in the morning, one with lunch and one before bed.

What is it?  Is this steroids?

Naw man, don't worry about it.  Pop one right now.

Nathan thought about it briefly, but wanted to prove his loyalty to the team so badly, he took one on the spot.

Cool, that'll be your mid day one, just remember morning, noon and night, one pill.

OK.

That night Nathan took a pill before bed.  He hoped it would work.  He sure liked being on the team and hanging out with the guys.

After a few weeks, Nathan still wasn't seeing any results.  In fact his body had become softer and weaker looking.  He asked Brad, but was told not to worry, it was just his body getting used to the pills.

After two months, he noticed the guys checking him out in the locker room when he was changing.  Did he have toilet paper on him or something, what the heck?  A couple of the guys elbowed each other and nodded toward him and laughed.  Maybe it was because his butt was filling out.  He had to buy new jeans that were bigger, but they still didn't fit well.

After three months of the pills, poor Nathan had developed small tits and big nipples.  He was freaking out when he noticed it.  No way he could change in the locker room looking like that.  He stopped and admired his tits in the mirror.  He felt strange, like it was his true self and he liked what he was seeing.

Brad's sister Jenn was the "It girl" and Nathan felt special when Brad suggested they go to the mall to shop together.

At first it was just Nathan following her like a puppy dog, she was so beautiful and curvy.  They went to all the women's shops.  Then they hit a unisex store and Nathan started looking at jeans.

Try those on, Jenn suggested.

When Nathan came out of the dressing room, Jenn nodded her disapproval.  No, those don't fit very well at all.  Try another.

Nathan tried several pants, but none fit at all.

Then Jenn handed him a pair of jeans and said, try these.

To his amazement, they fit really well. 
I guess women really are good shoppers, he thought to himself as he exited the fitting room.

Yes, those look great! Jenn said.  See told you we'd find something for you.  Now go ring those up.

When he got to the counter, the pretty sales girl took the jeans from him and zapped them with the scanner.  She looked at the screen and then paused briefly and snickered.  Oh, you're lucky those are on sale today.

Nathan thought it was strange, but whatever, he didn't care at least he found some jeans finally.

The next day he could hardly wait to wear his new jeans.  He put them on.  They were kind of low on his hips, but man they fit so well.  He wore a long t shirt on top because his flat belly kind of showed above the waistband.

Later in the locker room all the guys were complimenting him saying, nice pants.  He caught a few of them nudging each other and snickering.  Nathan had moved his locker to a back corner of the locker room so people wouldn't see him change.  He looked around to make sure he was alone then quickly removed his shirt.

Brad showed up suddenly and Nathan freaked out, crossing his arms in front of his chest trying to cover his breasts.

Dude, WTF?  It's just me man.  Wanted to give you some more pills, you must be running low by now right?

Nathan tried to act casual, as he turned his back toward Brad and grabbed a shirt from his locker and slipped it on.  He hoped Brad hadn't noticed his tits.

Oh, yeah, I'm almost out.  Thanks man.  Do you think they're working? 

Definitely, I'd say your body is responding way better than I thought.  Keep taking them.

For sure man.

Nathan felt so special that Brad had taken the time to help him.  For some reason he liked that he was doing what Brad told him to do.

To Be Continued...