Ryan becomes Jennifer

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Young man is disguised as a babe to hide from the bad guys.
3.5k words
4.44
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Part 1 of the 5 part series

Updated 09/21/2023
Created 04/18/2023
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"Hold still, Ryan."

"Are you done?"

"Relax, I'm almost done."

"You said that five minutes ago."

"You keep fidgeting and slowing me down."

"Let's just say I'm a bit anxious right now."

Andrea sits back and looks at me sympathetically with a frown, "I know you are hun, it really sucks. I wish there was some other way."

"Me too." I say thinking back to yesterday afternoon. I was walking back to my apartment in south Philly when I cut across a tiny park towards an alley. It's a short cut I've used forever. As I rounded the corner of a building I saw a man on the ground with his hands up in a defensive posture as two men were pointing guns at him.

In the span of maybe five seconds they shot him and looked over and saw me and I saw them. I knew both of them, not personally but I knew who they were.

One is a city cop, a bad one that has a reputation as being dirty. His name is Ken Sterling. He's known for stealing money from drug dealers, drug addicts and basically taking money from other bad people to look the other way. The other guy is Drake Williams, a known drug dealer and overall badass.

They didn't shoot at me but they did begin to chase me and I ran like I've never run before. Knowing this area so we'll I was able to get away in less than a block and even make it out of the city.

I knew for a fact they didn't personally know me either but I am from the neighborhood so finding out who I am probably wouldn't be hard. I'm not very big, five five, one twenty five with long brown hair. I have a hint of asian ancestry with a light tan complexion.

I had gone over to New Jersey via an Uber and went to a liquor store then to a park where I called Patrick. He had me stay put until he could come get me.

At first we both figured they didn't know my name so finding me would be difficult. But then my sister called and said the cops came around my parents house asking to speak to me. That's when the terror set in. Yet it only got worse from there.

"I'm serious Ryan, I'm just about done and then you can look for yourself." Andrea says a bit impatiently.

"Thank God." I sigh.

"Patrick is going to shit his pants when he sees you?"

"Why?" I ask suddenly panicked.

"Because hun, you're a babe. I mean you're stunning. Just as I knew you would."

Once we found out they knew my name Patrick called his cousin Andrea and asked her for help. That's how we wound up at this hotel down by the airport. Andrea rented this room and that's how we got in here. But then we were told from a friend in the neighborhood that the cops are now looking for me in connection with several armed robberies!

That's when Patrick and Andrea came up with this brilliant plan to disguise me, as a girl.

I vehemently opposed this plan until reality stepped in, this wasn't a game. Those men are dangerous and I could end up un-alived. I'm not ready for that.

Andrea's friend owns a house down south in North Carolina with zero connections to me except for Andrea. I have never met the guy and apparently I can go stay there for as long as needed.

As long as I needed.

What did that mean, well Patrick said he needed time to figure out how to clear my name and get the cop and bad guy to leave me alone.

"There, all done." Andrea says sitting back smiling at me. She looked so proud of herself as she looked at me.

"Can I see?"

She nodded and I turned around looking at at the mirror.

It was me but it wasn't me at all, I was looking at an incredibly cute girl. My eyes dark and sexy with a cute button nose and those lips, my lips are so full and pouty. My face looks thinner, my cheekbones seemed softer and higher.

I was stunned at the transformation but it wasn't over. Before Andrea began the makeup/makeover tutorial she had had me shower and shave everywhere, not that I had much to shave. I have been baby face my entire twenty four years and not much body hair.

But she had me shave my privates, little did she know I always do that. One never knows when one will get lucky. She told me to shave my legs and armpits too.

I had asked why and she said I have to be convincing all the way all the time. I'm going into hiding until Patrick and his Uncle, her father, can figure this out for me. When I made the comment that I'll be far away where nobody will know me she said armed robbery suspects go out on a national data base. Something as simple as a traffic stop can get me caught.

"Now it's time to get dressed, ready?" She asks.

I'm still staring at the cute girl in the mirror and smiling. I can't believe how pretty I am. It's actually kind of turning me on.

"Where is Patrick anyway?" I ask as I follow her back into the bathroom.

"My dad and him are getting a friend of his to get you some new identification, birth certificate, social security card, drivers license."

"How are they gonna do that?"

"I don't know and the less you know the better off we all are, okay. Now put these on and these go in the bra." She says

I knew about Pat's uncle being a former cop but I didn't know he had so many connections.

I stare at the white panties and bra and two fake boobs. I sigh before taking them and looking at her waiting for her to leave. I was currently only wearing a robe.

"Oh, you want me to leave?" She says teasingly.

"Go!"

She giggled and walks out leaving me alone.

I take off the robe and pull on the white satin bikini panties and instantly get hard. My little dick is so sensitive now. I pull on the bra and put the fake boobs in as instructed.

"Now what?" I call out through the door.

"Now come out here so you can try on these clothes."

I'm standing in the bedroom a little embarrassed as my dick is making a small tent in the panties and Andrea is looking right at me.

She is definitely cut from the Irish cloth that Patrick is, black hair, pale skin blue eyes and oh so beautiful.

"This won't help so we're gonna have to do something about this." She says pushing me back in the bed. "This is a one time thing."

Andrea gets on her knees between my shaven legs and pulls the white panties down and puts my hard little dick in her warm sweet mouth.

This is only the third time in my life a girl has gone down on me. Unlike the other two girls Andrea makes no comment or snide remark about the size of my small penis. She just gives me a nice smile as she goes to town down there.

I can't believe this beautiful girl is sucking my dick so sweetly and she definitely has done this before. He lips are wrapped firmly around my little cock while her tongue is massaging the underside. I don't last very long letting out a long moan as I squirt my load in her mouth. It's even hotter as I hear her swallow it all down.

As quickly as I finished she was back on her feet smiling again. "Now catch your breath and let's get busy.."

I was really catching my breath and panting a bit but I was smiling at her like I've never seen her before. She really was adorable.

"Okay stop looking at me like that. It was just a blowjob. Now get up and let's get busy." She said changing her tone.

I tried on so many clothes watching Andrea toss this or that aside was dizzying. I can't even say for sure how long we had done this but she had made a pile of what I was taking and what I was not. Andrea is a girly girl and wore lots of skirts, mini skirts mostly but also midi and pencil and maxi ones. And several dresses and tops. The shoes seemed to turn me on the most, I liked the heels and wedges, boots and sandals.

Finally, "Damn you look great." Andrea says stepping back to really look me over.

I'm looking at the cute girl again in the full length mirror only she really looks hot now. Her long brown hair cascades down her narrow shoulders over red and black sweater. Her bosom is nice as the sweater hugs her feminine figure showing her small waist and flat belly down to the black cotton mini skirt. The hemline so short it shows her long shiny tan legs all the way down to the black ankle boots which are so adorable.

She turns left and right, all the way around and I am just floored at how Andrea made me a girl in just a few hours.

I look right at Andrea and ask timidly, "be honest, do I look like a boy in girl clothes."

She laughed sarcastically, "no hun, you look amazing."

Andrea and I spent the next half or so packing up two suitcases with what I will be taking on my trip. As we worked she talked about how I must train myself to be more feminine in all my mannerisms from walking to talking. The way I sit to how I relax, "and stop slouching!" She kept telling me.

At one point she ordered pizza and went to get it returning with beer, a bottle of rum and the pizza.

As we ate she said Patrick had called and there was a plan in place. He would be back in a few hours and she would have to leave me soon.

This terrified me and she kept me calm telling me nobody will find me here and Patrick will be back soon. I just have to be patient. I asked her why she has to go and she replied that Patrick says we have to maintain our normal lives in this abnormal predicament. They can't draw any unwanted attention.

Before Andrea left she took me in her arms and held me tightly. Then at arms length she looked me right in the eye and said, "if you could see what I see you will embrace the new you and enjoy being a lady." She had given me a big hug before she left and told me everything will work out.

Then she was gone and I was alone. At first it was fairly scary but after I had a stiff drink I relaxed a little. I tried watching tv but I was too anxious and Patrick had taken my phone so I just sat there in the room with my thoughts and that was a bad place to be.

I couldn't get over my legs, they're so hot I kept running my hands up and down my thighs. I wanted to play with myself but I didn't have time not knowing when Patrick would be returning.

Still though, I really look like a babe and I felt extremely hot. I went to the mirror and stared for awhile at my face and that still blows my mind. I can't believe how pretty I am and Andrea didn't put the makeup on heavy or anything, she said she was just highlighting my eyes and nose. She told me my lips are naturally full they just needed a help with a pencil and a little lipgloss. With my hair parted to the side partially covering the side of my face I look very different.

My figure is incredibly hot and I never noticed this before. I have this tiny waist, flat tummy and girlish hips. When I turn sideways the profile is sexy as fuck! I follow that line from the small of my back that curves in and makes my butt stick out I just have to touch it.

I walk around the room looking in the mirror at how I walk in these four inch black booties and practice walking like a girl. It seems I have a knack for it and I really love this look.

After awhile I'm starting to get tired and sit on the edge of the bed and kick the boots off. Then I lay back and try and try and nap but sleep is not coming easily.

How long before Pat gets here? When am I leaving? And how am I getting to where I'm going?

I awake because someone just sat on the bed next to me.

It's Patrick.

He's a badass but never comes across as one. He's very smart yet has a tendency to do dumb things. He's charming and sweet but he's also very humble.

He has wild short black hair and deep blue eyes with sharp handsome features. Both his ears are pierced, he has tattoos up and down both arms as well as his torso and legs and he's very muscular even though he's not big on going to the gym.

He's looking down at me with that smile of his and I can't help but smile shyly back.

"I had a feeling this would work." He says.

"Really?" I'm laying on my side, my head still on the pillow as I look up at him. He's much bigger than me but now I felt really tiny and vulnerable as I lay there.

"Yeah. Andrea told me to keep my hands to myself."

"What?! Move!" I say playfully as I push him away so I can get up.

"Wow," he laughed incredulously, " I mean fuckin wow! Do you know you're hot, Ryan?"

"Stop it! You're embarrassing me."

"Don't be embarrassed, own it girl!"

"You're weird."

"And you are now Jennifer Marten."

"What?"

"Here have a look." He sat back down on the bed and pulled out several items from an envelope including a driver's license, social security card, birth certificate and several other documents.

"Wait, how did you get this picture of me?" I asked a bit confused.

"There's an app and Andrea took a couple pictures of you while you guys were getting ready."

"Damn, Andrea is good. This girl is freakin pretty." I say looking at the drivers license."

"Hey," he says looking at me.

"What?"

"That girl is you. I told Andrea if anyone could pull this off it would be you."

Our eyes lock for a long awkward moment before I look away a bit sheepishly.

"When do I leave for North Carolina."

"Later tonight."

"How am I getting there?"

"You'll be going with my dads friend around 10. He'll take you to Harrisburg where you'll catch the last bus to Charlotte. Once you're in Charlotte you'll have to switch buses and go to Asheville. Once you get there you'll go to this address," he handed me a piece of paper, keys and a new cell phone.

"I have your number in my phone. If you know my number don't use it."

"I don't have your number memorized."

"Good. I will get in touch with you shortly after you get there. Maybe a few days. The number will be unknown, okay."

I nod.

"This is your bank account but it isn't effective until next Monday. You will have plenty of cash and these Uber gift cards. You'll have time on the bus ride down to create an account."

This was all too surreal.

"You have to resist the urge to call anyone you know. Got that?"

I nod.

"I'm serious Jamie, say it."

"I got it."

"No emailing, no social media to anyone you know."

"I understand."

I did understand and I was scared. Patrick is very sweet and tells me to stay positive, he and his uncle will get to the bottom of this.

Before the man that was taking me showed up I changed. I had picked an outfit for this trip because I'd be on a bus for the next day.

I wore a long black maxi skirt with a green top and a white hoodie. I wore plain white sneakers with this outfit.

It was really hard saying goodbye to Patrick because of the unknown and when this man in his fifties showed up I was already sad.

He's a big guy, balding with glasses and a big mustache. He doesn't say much he just gets my two big suitcases and puts them in the mini van.

Patrick gives me a long hug before I climb in and off I go into the unknown.

It's about an hour and half ride to Harrisburg and this guy is very quiet the entire trip. He asked if minded he smoked and I didn't. Other than that I was alone in my thoughts.

When we get to the bus terminal I have to buy my ticket and it will be the first time I show my ID to anyone. This made me nervous but Andrea had reassured me I look passable.

The man takes an exit and I can see city lights after being in complete darkness the whole way down the turnpike. He drives on for a little while longer before making another turn down a dark street before pulling over.

"I gotta take a leak." He says climbing out of the vehicle.

That was a bit odd I thought, he could've waited a few more minutes until we reached the bus station.

Just then my door opened and he grabbed my arm yanking me out of the car easily and holding me against the van. He opened the side door and forced me to sit down.

"You'll do exactly as I tell you or I go right to the cops and you, your friend and Harry are all in a world of shit. Got it?"

"Got what?" I ask terrified.

Whack!

He smacked me upside my head making me see stars.

"You're going to suck my dick right here right now." He says unzipping his pants.

"What?!"

He grabs my hair turning my head in an awkward manner and leans his pudgy face so close to mine I can smell his cigarette breath.

"You'll either suck my cock or I'll bash your pretty little face in and fuck your brains out. Now suck my dick."

For a millisecond I thought I should just let out my male voice and tell him he's making a mistake but he hit me on the side of the head again.

"Open that pretty mouth and suck my dick!" He yelled at me.

Terrified of this large man i stare at the cock in my face. It can't be more the six maybe seven inches but the girth makes it look more ominous. I open my mouth and gingerly stick out my tongue touching the head.

There's no real taste nor smell except for a musty odor. Timidly I move in closer until my lips are on the bulbous head. Again, it doesn't taste bad however I do have to open my mouth wider.

Then the head of his cock is fully in my mouth and I begin to suck gently on his member.

"That's it bitch now take more of it," he says breathing heavier now.

I have my eyes closed as tears stream down my cheeks. I push down a bit further as his fat dick fills my mouth.

"No teeth ya little cunt!" He yelled gripping my hair painfully.

I whimper and do my best to not touch his shaft with my teeth. Then he holds my head with both hands and begins pushing his cock in deeper then withdrawing.

In and out he began fucking my mouth.

"I knew you'd be good you little slut."

Then he went crazy on me and shoved his dick so deep in my mouth it went down my throat making me gag.

I cried out but he he did again and again. My struggles were futile and my cries overshadowed by his grunting.

How long could this last? My throat burned with every thrust. My jaw tired and I could barely breathe as tears stream down my cheeks.

Then he slammed his cock hard in my mouth and I tasted his thick slightly salty load as exploded. With each thrust he let more and more out holding my head in a tight grip making me swallow his entire load.

He held my head awhile longer until he nearly collapsed on top of me falling partially into the van.

I can barely breath but he gets off me and tells me to get back in the van.

At the bus station he took my bags out of the van and left them on the sidewalk and just drove off.

Good riddance.

An hour later I'm curled up in my seat, my knees drawn up as I stare out into the night. Finally sleep comes and I rest.

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4 Comments
AnonymousAnonymousabout 1 year ago

Despite the context, "bitch," "slut" and "cunt" are still offensive.

KatiwantsKatiwantsabout 1 year ago

Great start!! Can’t wait for more!!

pink4bbcpink4bbcabout 1 year ago

What a great start more please much more please don’t make us wait to long

Kathryn65Kathryn65about 1 year ago

Loved this such a great start more please much more xxx

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