Ryan becomes Jennifer Pt. 02

I've been in North Carolina for two weeks and I still can't get over how I look, how I feel and the overwhelming urge for a man's attention. It was definitely more than an urge it was a craving. Ever since that disgusting man forced me to perform oral sex on him I realized while at the Harrisburg bus stop my panties had gotten wet. The act had turned me on, not the man, nor his particular tool but the idea that I could make a man that hard.

The ride down I also saw how men looked at me, how a smile could make a man smile back. I liked this attention a lot. I never really caught the attention of girls like this but as a girl, I was the object of men's desires and I loved it. And having men flirt with me was a surreal experience.

Ever since I arrived in Asheville I began wearing everything Andrea had sent me down here with. Including lingerie and two bikinis.

One afternoon while taking a picture of myself in a white string bikini I was so shocked and so turned on by my own image I couldn't look away.

I was on my knees sitting back facing the closet that has a full length mirror on the door. I tilt my chin down, put the tip of my index finger right to my red lips in a pouty way and take the picture. Then I turn sideways, and my profile is hot. My chest looks small but fits small frame, my waist is tiny and belly flat. I love the way the string holding up my bikini curves up over my hip with the tie making the bow. I lay back resting on my elbows stretching out one leg while bending the other and take a picture. Physically taking that picture was a little awkward but I pulled it off. I would later find the timer on my camera and begin using that.

I had taken lot of pictures of myself in every outfit over the past two weeks and would go through them playing with myself. I couldn't get over the sexy little black haired girl with a beautiful slightly asian look. And my body was so feminine except for the lack of breasts.

My life up north had basically grounded to a halt. Pat had called me twice, the first time was to tell me that I could use the bank card now and I had more money than I've ever had in my entire life. He told me between my family and his I should be able to live comfortably until they have this matter resolved. I asked how long and he didn't have an answer.

The next time he called he said the police pulled him in for questioning but he didn't give them what they wanted. They also questioned my parents, my brother and my boss Alan. Nobody has seen me.

Andrea also called me and we talked girly stuff. She asked me how I was doing with my makeup reiterating less is more. I told her I had pretty much tried on everything she sent me with. Then she asked me how the men are treating me and if I hooked up yet.

I wanted to tell her about that pig of man in Harrisburg but I didn't. I did tell her the men seemed very friendly and interested in me and I lied saying I don't want that. She asked me why not, I should enjoy my new femininity and embrace it. She went on and on about how adorable and sexy I am and who knows, maybe I'll meet a guy and fall in love. But, she stressed, do not try and fool a man. That could be dangerous. She suggested websites for girls like me. She told me lots of men are into girls like myself.

That one call from Andrea is what began my journey into a rabbit I would never come out of again.

I did find the websites Andrea was talking about and taking all those pictures of myself was about to pay off. The website I joined (I won't name it) asked me to create a profile. My name Jenni, my age twenty four, my town Asheville (I almost put Philly) and I had to describe myself then what I am looking for in a man.

Briefly about me I said I am very new to this and I am sweet and shy. I am looking to explore my new femininity and I love being very girly.

I honestly was loving all the dresses and skirts and heels.

Then what I was looking for began with a gentleman, a man that knows how to treat a lady properly and wants that girl to treat him like a king. I'm not into anything rough or kinkier than me dressing up. I'd like as normal relationship as possible with a nice man.

Then after making the payment I submitted my profile.

My days have been fairly mundane so far as I don't know anyone or even know what there is to do here. I have been to the grocery store, the liquor store and a gas station for beer and each time it was an adventure in being a girl. One man at the gas station asked me to marry him. It was all in jest and he was smiling but it really turned me on.

The house I'm staying at is a small two bedroom one bath with an open kitchen dining area and a cozy little living room. There's also a patio on the back and the house is on a hill over looking the northwest side of town. I did find a park in walking distance up the hill from me and I did walk up there a couple of times.

The day I sent in my profile I decided to go online shopping for some very cute very sexy outfits and I spent about five hundred dollars on clothes and shoes. That was about my limit for extravagant spending so I'd have to be a bit more frugal from now on.

I showered, shaved and slipped on black leggings and a tank top and headed out for a run up the hill and through the park. Not very much to say about it except the park is beautiful and the run was exhausting.

It wasn't until later in the afternoon when I finally checked that website to see if I had any responses and I was shocked!

There were so many men that sent me messages and the likes I received for the three pictures were overwhelming. I spent the next few hours reading the messages, sending back replies and looking at the pictures of the men.

Too many were just dick pics and I dismissed those. I also dismissed the ones I didn't find an attraction to. After all was said and done I settled on two in particular.

The first guy was Charles, a fifty two year old man that was very handsome and dashing in the few photos he had in his profile.

He has salt and pepper brown hair with a matching light beard and he's built husky, not fat at all just big. It says in the furniture business as a salesman and travels a lot. He likes the ocean, the mountains and movies. And he's looking for a sweet young 'gurl' to spend his time with.

We began corresponding on the site before we changed to texting. Then by nine that night he asked if we could speak on the phone. He wanted to hear how I sounded in person.

Nervous but also very excited I said yes.

A moment later my phone rang and I answered, "hello."

"Well hello darlin, how are you?" He says with a very deep southern drawl.

"Hello Charles."

"I like that voice, it's very sexy."

A weird thing happened when that pig forced me to suck his fat dick, he hurt my throat and my voice went a little higher and raspier.

"Thank you."

"And that northern accent too. I like it."

"Charles, can I ask you why is a man like you on a website for girls like me?"

"Well sweetie, after two failed marriages I thought a change was in order. And having been all over the world I have met some very interesting people. My last relationship was with a young lady like yourself and it was wonderful."

"So what happened?"

"She wanted to see the world so I had to let her go."

"That was very nice of you."

"It was just the right thing to do."

I liked how he said thing, it came out as 'thang'.

"So I'd really like to meet you."

"Okay, when?"

"How about dinner Friday night? I know a very nice place."

I can't believe how fast this is moving. "Sounds good."

"You are full time." It wasn't a question.

"Yes. Is that okay?"

"Sure is sweetheart. Can I be honest with you?"

"Of course."

"If you weren't passable we wouldn't be talking."

"Well good for me then." I quickly went back to his profile and reread it and saw it clearly now, he's is looking for passable only. The quote 'must be passable and willing to be out in public' I must've missed.

Friday is two days away and we did keep in touch a lot. Mostly by text and him asking me to send him pictures of what I was wearing at any given time. I said at one point I don't change outfits that often. He replied with he'll make sure I have enough to outfits to change as often as I want.

Guy number two is a man a few years older than me and he's a total geek with a very cute sweet appeal. His name is David and he's twenty nine, never been married, hasn't been in a relationship in a couple years and identifies as bisexual except he adds, he seems to only meet gay men.

He's tall and lanky with wild black curly hair and baby face with big blue eyes behind black rimmed glasses. If he's going for the nerdy look he's definitely nailed it. What instantly attracted me to him is he said in his profile it would be nice to have girlfriend that would dote on him as he would her. And that he does know what to do with a girl like me.

We started very slow as in, I didn't receive a response back after I replied to his original message until the day of my first date. He apologized about seven times in his message stating life got a bit lifey for moment. Then we messaged until I had to get ready for my first ever date with a man as a girl.

It was a bit on the chilly side for a late May evening so I wore this snug black midi skirt, a blue satin top with spaghetti straps, pantyhose that feels exquisite on my freshly saved legs, and black velvet ankle booties.

I brought along a black leather bolo in case I got real cold.

Charles is picking me up and waiting is not one of my strong points so I had a couple quick shots of fireball whiskey to help calm my nerves.

Charles arrived promptly at seven and rang the doorbell which I had never heard before and it kind of startled me.

I walk femininely to the door and there is this very large, very handsome man standing there in a blazer, button down blue shirt and khakis with cowboy boots.

His smile is genuinely warm as he offers his hand, "hello Jenni, I'm Charles and I'm very pleased to meet you."

I actually gave him my hand as a lady would and we shook. "Hello Charles."

He led me down the pathway to his car and opened the door for me. This skirt while it does have a sexy side slit still restricts my legs a bit and I have to turn and sit before lifting my legs in. I've seen many women do this.

"Good thing I didn't bring the truck?" He said with a chuckle watching me get in.

The drive into town was quite brief and I did notice him looking at my thigh when the slit opened.

He smiled knowing I saw that but he was confident enough to pull that off.

When we arrived he pulled in front of this very nice stucco building and a valet walked opening my door allowing me to exit first as Charles came around the car a gave his keys to the young man.

Apparently Charles has been here before because the host greeted him as if she knew him personally. We were led to our table in this dimly lit restaurant in a nice cozy corner and took our seats.

"You didn't even notice that did you?" He says as settled in.

"I'm sorry, notice what?"

"Every man in the place checking you out."

I blushed, "not at all." I say really blushing.

Charles told me about his work, how he travels all over the world and some of the beautiful places he's been. Our dinner was amazing, the wine tasted like nothing I've ever had before and the dessert was delicious.

Before we left he leaned in, his hand touching my bare thigh giving me chills and told me how delighted he was that we have met.

He offered some suggestions as to what we could do next, coffee at a cafe, a night club, a drink someplace or a walk in town. I chose a drink. Then he asked, a local bar, his place or mine?

I said my place.

We arrived back at my house and I bought out a bottle of Gentlemen's Jack. A little joke to myself as Charles had been the perfect gentleman all evening.

"When you say you're new to this Jenni, how new are we talking?"

"Within the last few weeks."

"That's incredible."

"Why?" I ask.

"Because you are gorgeous and extremely feminine. You've been dressing your whole life I guess."

This is the part I don't like, lying. "Yes, but it wasn't until recently that I decided to be myself."

"And you moved away from your family, friends. Basically your whole life?"

I nod, that question stung with sadness and I guess he saw that because he directed the conversation away from that part.

"So what is it you'd like to explore?"

"Explore?"

"Yes, you're new found femininity, as you stated in your profile?"

"Oh, well, hmm," I was instantly embarrassed by that.

"It's okay. I'd like to help you."

"How so?"

"C'mere babe." He says patting his lap.

The blushing seems to be getting normal for me but I get up anyway and take the two steps and gently sit on his leg. I find his leg is big, powerful and it's almost like I made no difference sitting down.

He slipped his arm around my waist and pulls me back so I'm now resting against him and I feel his breath on my neck giving me sweet chills.

He takes a deep breath, runs a hand up my leg and says, "tell me what you would like to do and let's make it happen."

I knew what I wanted I just didn't know how to express myself. Sensing I was hesitant he put his hand behind my neck and gently pulled me forward and kissed me on the lips very gently. His beard lightly tickling my face but his gentle lips on mine overcame that as I relaxed a bit putting my arm around his broad shoulder and kissed him back.

When his tongue forced its way into my mouth I gave a little whimper but oh did I get into the kiss even more. I've never been kissed by a man and here I was, on a man's lap being held and kissed passionately.

I wanted to be his so I broke the kiss and sat up straight, "maybe you could give me five minutes then come back to my room?"

He nods slowly, smiling, "sure sugar, I'm going to grab my overnight bag. Is that okay?"

I leaned in and kissed him deeply showing him I wanted him to stay.

I told him which room not that I'd be hard to find and I went in quickly stripping out of this outfit for a sexier one.

I slip a black lace thong on first then grab this tight black lace and sheer dress that barely covers my butt and the front. It's off the shoulders with long sleeves and feels extremely sexy as it hugs my body.

I grab a pair of white ankle socks that have sexy ruffles at the top and slip these on each barefoot then slip my feet into a pair of four inch open toe shiny black pumps.

I light a couple candles, quickly ran a brush through my hair and waited a moment before I heard him walking down the hall towards my room.

My heart pounded, I felt like it would burst out of my chest and then he opened the door and stood there looking me over from head to toe and back again. A big smile appears on his face as he walks over to me.

He takes me in his arms again as I put my hands on his big chest and we kiss deeply again and I can't help the soft whimpers escaping me.

He pulls away and holds me at arm's length looking me up and down again.

"Darlin, you don't look like you're new to this at all."

"Thank you."

He let my hand go and took a few steps back, "please walk over here baby."

I've been walking around the house in heels for two plus weeks now and watching videos on how to walk as well. Doing my best seductive walk I went right up to him and back into his arms continuing our kiss as sweet as possible.

His hands slide down my back and over my ass as he gives a nice gentle squeeze causing me to moan as we kiss.

He leads me back to the bed as we kiss then pulls me down on top of him. His hands run up and down my back and over my ass and this is driving me crazy. I know what I want and there's only one way to get it.

I push myself up as I straddle his groin and begin unbuttoning his shirt nice and slow. This has to be a show in my mind. I am the sweet innocent girl in a porn and she knows what she wants and how to go about it.

I'm pleasantly surprised that he's not super hairy just a small patch on his chest.

I lean down and kiss the center of his chest while his hands continue to grope my ass and thighs.

I push myself down further placing little kisses down his torso as I work toward his midsection and reach his belt.

I'm on my knees between his legs as I rub my hands over his crotch feeling his dick is already hard. I concentrate all my attention right on the outline of it as I keep looking into Charles' big brown eyes.

As my one hand traces the outline the other slowly and bit clumsily unbuckles his belt. At last I get his pants undone and I use both hands to pull them down.

Everything I've done and I'm about to do is from watching videos and I feel confident enough to continue as Charles seems to be enjoying this.

With his pants off now and him just in his blue briefs the obvious mound laying to the side seems to be throbbing a little. I lean all the way down opening my mouth and grasp his cock with my lips sucking through his briefs.

"Oh shit Jenni." He moans.

I run my mouth down over the length of his shaft and back up again. This is making me so hot and I can tell he's enjoying this as well and I couldn't take it any longer and I pull his briefs down revealing his cock.

It's not as intimidating as the last one yet it's still much bigger than mine. The mushroom shaped head is a reddish color while the shaft is lighter with veins criss crossing here and there.

When I wrap my fingers around it his cock makes my hand look so tiny lifting it straight up. It so warm and soft yet so rigidly hard.

There's a droplet of precum at the tip and this is where I began.

I ran my tongue gently over the tip barely tasting the precum. I swirled my tongue around the head just before I sweetly enveloped the head with my lips then my mouth.

"Good girl that's so nice." He says with a hand on my head.

Him calling me 'girl' felt so delightful I turned up the heat taking more of his cock in my mouth.

This was so much nicer than being scared to death and forced I couldn't help myself sucking Charles' cock so I went down on him even more.

He moaned and I whimpered as my nose touched his well groomed pubic hairs as my tongue worked his shaft with his entire cock in my mouth and down my throat.

I began to slowly bob my head up and down the length using my lips and tongue mostly and when I had him all the way in and down my throat we would both moan.

"Such a beautiful girl giving amazing head." He whispered as I sucked the tip for a long moment then go all the way down. I repeat this over and over.

"Seems to me you have done this before."

"Once." I say releasing him briefly.

"Just once?" He asks with a raised eyebrow.

"Mmhmm." I mumble as I glide my lips down the side to his balls first sucking one then working on the other before running my tongue all the way up his shaft to the tip.

I stroke him with one hand while I cup his balls with the other sucking on the head and swirling my tongue. I can tell he's getting close as he's breathing heavier and starting to tense his legs and torso.

"What a good little girl. Open that pretty mouth so I can watch you take my load."

I slowed my rhythm and opened my mouth wide with the head of his cock resting on my tongue as I continued to stroke him. Our eyes are locked, he's just about to explode when it hit me, I'm no longer Ryan. I'm no longer a man.

I am Jennifer and I am willingly and eagerly about to take another man's load!

He groans and tenses up as his first rope of cum shoots out covering my upper lip and into my mouth. Before the second shot I wrapped my lips around the head as his cock pulses and shoots more and more. It's all I can do to swallow as he continues to shoot his thick creamy load down my throat.