My transistion part 3

Post time12-02-2021, 00:48
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Part 3... Jill meets a guy and Lisa teaches Jill a lesson.
As always I look forward to your comments or requests.

Jill has been working for almost four months now. It's been very busy and getting busier every week. Now that we got the contract to fix and setup all the computers in the public schools in the area. Jill was looking forward to getting some overtime. Ted hasn't been seen once by Jill.
Then one day Jill is called to Ted's office. I wonder what he wants Jill mumbles to herself as she leaves her work area and heads up stairs.
Jim's secretary looks up at me and says, he's waiting for you. Please go right in.
Jim's secretary is a hot little number. About 21 or 22 years old 5'8" 125 lbs nice tits with blonde hair and brown eyes. It's obvious what she was hired for as she knows nothing about being a secretary.
Taking a deep breath and walking into his office I put my best smile on and said, Ted, it's been awhile, what can I do for You.
Sit down Jill. I want to talk with you.
He sits back in his chair and puts his hands behind his head.
I'm in a position to help someone out. You see the company has grown so much that the big bosses want to promote someone to a manager. They left it to me so I thought you would like it.
It means you'd be working up here in your own office of course.
I don't think... I start to say but am cut off.
Please think about it Jill. Ted says.
Listen, I'm sorry about what happened between you and I. I'm a guy and your, well you know.
Your a pig I'm thinking!
Ya I get it Ted. I'll think about it.
Good, can you let me know soon. They want an answer asap.
Okay I'll talk it over with Lisa this weekend and let you know Monday Ted.
Your by far the most qualified for the job Jill. You know that right, as he gets up and offers a handshake.
I stood up and shook his hand then turned towards the door.
Jim's secretary Daphne Open's the door as I reach for the handle and enters saying excuse me sir but John Withering is here to see you.
I squeezed by Daphne stumbling into the lobby, there's this large hand that catches me as I fall to the ground. The bitch tripped me I'm thinking as I look up at this very handsome guy. He pulls me up from the floor saying, are you alright mrs.
Somewhat embarrassed I say oh yes thank you.
I can feel myself blushing.
Daphne chuckles as she stands there.
Are you sure your okay mrs???
Preston I respond, Jill Preston.
Pleasure to meet you mrs Preston, I'm John withering.
John has to be 6'3 or 6'4 about 35 year's old with light brown hair and shockingly bright blue eyes and from what I could tell was fairly muscular too.
As I steady myself and John let's me go. Ted comes rushing to the door and pushes Daphne aside to see what's going on.
John I'm happy to introduce you to your new manager, that is if she takes the job.
Well is that a fact mrs Preston.
I was just offered the job so.
She would like to think it over for the weekend and will let me know Monday morning John, Ted says.
Thank you again, both of you I say as I head for the hall.

You seem distant tonight Jill. Is everything okay.
I was offered a promotion today but I'm not sure I should take it. I told Lisa as we ate dinner. Well that doesn't surprise me. Your wasting your time doing what your doing, dose it come with a raise too.
I don't know. I mean I didn't ask.
Well we could use the money so are you gonna take it.
I think so. I have until Monday.
Good. Do you want to go out for a walk or something Lisa asked.
I meet a guy in Ted's office today. He's the owner or something.
Oh, is he good looking? Lisa enquires.
Ya! I mean I think so.
Laughing, Lisa says it's okay to be attracted to guys you know, after all your a woman she says a little apprehensive.
I know but it still feels kinda gay to me.
You know Jill. It's not gay or straight. Your human! You used to be a man and though it's not your fault what happened to you. You have a right to be happy.
Even a couple months ago I still felt like a man in my head but I have a body that is very much female. It confuses me from time to time and though Lisa's comment hurt, I know she means we'll.
It's been over a year now Jill. I think you should explore your feelings, what can it hurt.
I'm with you Lisa, I love you.
I know Jill, but I also know your interested in guys. At least a few have made your heart skip a beat once in a while. I see it. Think about it. I'll always love you and be here for you.
We kiss while we are washing the dishes, then go to bed.
I have a confession Lisa.
Lisa looks at me and says, what's that?
I played with your toys, I hope your not mad. I said.
Lisa smiles that devilish smile again and says, witch one?
In a shaky voice I tell her the big one that feels real.
What did you do with it, did you suck on it?
Smiling a little I said no.
Did you put it in your... I cut her off.
Yes I did, smirking at her.
How much of it?...
Lisa, this is a bit embarrassing you know.
I can't take all of it, I was just wondering if you could.
I paused for a moment as Lisa looks at me and says, you took it all didn't you?
I swear, I didn't think it would fit but when I cummed, I got so weak and I slid all the way down.
How did you feel.
Are you kidding me, it hurt like hell. I screamed out loud and Berry came banging on the door. I had to answer the door to tell him I slipped in the shower.
OMG, Berry, what did that worm say.
He just wanted to know if I was okay.
So...
So what, I say.
We're you thinking of anyone in particular?
No. I mean I was thinking back to when I was, well you know a man and what the girls I was with must have felt like.
Sure you were. You were thinking of cock Jill. And you got off on it. Nothing to be shy of.
I guess so was my response in an upset voice.
You see sweetie there's nothing to be shy about. Your a beautiful woman and you got urges that your exploring. That's all.
I don't want to talk about it okay. Let's just go to sleep a say. Lisa just grins and agrees as we snuggle together.

Monday morning I arrive at work my usual half hour early. Ted's car is here already so I head upstairs to his office.
Daphne is not here yet so I knock on his door.
Come in says Ted.
I enter his office to find Ted and John inside talking.
They both stand and offer me a chair.
As I sit I start out with...
Thank you for this opportunity but I feel I need to tell you something about myself.
Nonsense John says. I've talked with Ted and read Ted's progress reports on you Jill and your by far the most qualified to fill the position at hand. Is it about the pay Jill because it's negotiable!
Maybe we should allow her to explain what she's feeling, Ted replies.
Just then the door opens and Daphne is standing there with a cup of coffee. Oh, I'm sorry. I wasn't expecting all of you here. Dose anyone else want a cup of coffee.
I started to think that if this bimbo could get a job here that maybe I should take the job.
What kind of pay are we talking about if I do take this job Mr Withering.
Ted looks on with interest.
Mrs Preston, I thought you might join me for dinner tonight so we can discuss the details in private. That is if your husband is okay with that, he fishes for an answer.
Oh, I'm not married I respond.
A slight smirk is visible now as he speaks.
Boyfriend then, I'm sure!
I don't know what came over me but I giggled and said no. No boyfriend either.
Well then I'll send a car for you tonight at 7 pm. If that's okay?
I was feeling like a little girl in a doll house when I heard myself say ok.
Good. I'll see you tonight then as he gets up and offers me his hand.
Thinking he wanted to shake on the deal I offer my hand in return.
He bends down and gently kisses the back of my hand.
I could hear Daphne sigh slightly.
I felt like a princess or something as I left the office.
The day went by rather quickly as we were busy as usual.

I arrived at home on time and sat in the kitchen. Lisa was just getting out of the shower.
Lisa, I need your help in a big way. I have a business meeting tonight. John is sending a car to pick me up at seven.
John hay. Sounds interesting.
Ya well I really want to impress him so can you...
Of course Jill. I'd be happy to get you ready.
No, no, I don't think you understand. It's a business meeting to discuss the job I took. You know, wages, benefits that sort of thing.
Benefits, I bet she teasingly responds.
Somewhat embarrassed I say in an angry voice. Never mind, I'll get ready myself.
Lisa starts to laugh as she says I'm only kidding with you. Relax!
A tear escapes and falls to the table.
Jill, are you okay? Lisa puts her hands on my shoulders.
I start to cry and hug her tight.
It's okay Jill. I'm here, it's gonna be okay.
I was so embarrassed at what I was feeling. I didn't want her to know I liked John as much as I obviously did. I surprised even myself.
Lisa hugged me tight as she spoke.
This is what I was talking about the other day when we were talking about guys. I'm glad your feeling this way. Easy now, I'll help you. Go have a shower and let me get things ready okay sweetie she says.
I got undressed and into the shower. I shaved my body of all the hair I had. I was smoth everywhere.
When I got out she was sitting by the vanity. Wow. I've never seen you shaved! Looks good girl. Come sit here. I've got work to do.
As I walked over to her with a towel wrapped around myself, I noticed a bunch of clothing lying out on the bed.
Jesus I whisper as I sit.
How much do you like this guy Jill? Lisa starts out saying. I mean are you ready for a man?
I was still looking at all the sexy items on the bed as I say. I've only met him twice and both times were only for a couple minutes. Looking back at Lisa, she has that devilish grin again.
No, not so fast I say. Business meeting remember.
Of course. But one he'll remember, right.
Now I've got a grin on my face as I respond. Definitely one he'll remember.
Good. Lisa says as she starts with my makeup. She worked on my face for what seemed like forever. Not letting me see. Foundation, blush, eye shadow, eye liner, lipstick, lip gloss and finished with a squirt of perfume behind each ear. Then brush and style my hair. Next we started to dress me.
First the black embroidered thigh highs and garter belt, a sexy pair of black lace panties that didn't cover much. A black lace underwire push up bra that separated my Brest's with a red rose in the middle came next. Then a thin gold necklace with a heart pendant followed by some medium sized hoop earrings, a couple of bracelets and a small diamond ring.
I noticed Lisa was getting turned on but I didn't have much time to play. So I let her continue.
Lisa looks me over and says damn this guy is lucky.
I just smile at her and told her she's the lucky one because I'll be coming home to her. Lisa liked my comment and said, can't wait babe.
Next came a skin tight white dress with red markings in an unrecognized Pattern that just barely covered the top of my stockings and showed plenty of cleavage.
I've always had a girlish looking body so this was making me feel quite feminine.
Next came a pair of red and white high heals that strapped up my calf.
Can I look now Lisa I begged.
Not yet. You need a... she stopped and turned to our closet and returned with s thin red belt. Wrapping it around my hips she says, this will keep your dress from riding up when you sit.
Okay. Can I look now I say.
Just then there was a knock at the door.
No time girlfriend, Lisa says as she hands me a light cover and a white purse while pushing me to the door.

Lisa opens the door and there stood a man in a tuxedo.
Excuse me madam. Is there a miss Preston in the house.
Lisa looks at me behind the door and says, yes sir as she opens the door all the way.
Mr Withering is waiting for you my lady as he bows his head to me.
He offers me his arm and I accept. I'm escorted to the limo waiting on the street.
We don't live in a rich part of town so it must have been quite a sight for the locals.
I felt like a princess again as I got into the car.
When we arrived at the restaurant, I was greeted at the door by Mr withering. He offered me his arm as we walked into the lobby.
Mr Withering, right this way.
We were escorted to a private room with just two chairs and a beautiful table set with the finest dinnerware. Mr withering pulled out a chair as I sat.
I was feeling overwhelmed but loved the attention.
Some wine a servant asks as John sits down.
Yes please I replied.
As I sip from the wine glass John says I very delighted you could join me tonight miss Preston.
Looking him in the eye I respond. Please, call me Jill.
Of course, but only if you call me John?
I was definitely feeling a spark between us. But was he feeling it to. Or was he just trying to seduce me.
John it is.
So Jill, tell me how is it that someone as stunningly beautiful as you is still single?
Well I'm not exactly single. You see I'm living with my girlfriend Lisa.
Oh, I see you have a roommate?
Umm no, she's my lover! I flat out told him.
With a slightly disappointed look on his face he surprises me and says we'll I hope she's willing to share you with me!
Well time will tell now won't it, is what comes out even though I wanted to say no. I want you to myself.
So how is it that such a distinguished, handsome successful man such as yourself is left to hit on little ol me.
Well thank you, I haven't been complimented in quite a while. But to answer your question with success come the rift raft. And we'll I'm to busy for that.
And how do you know I'm not like all the other girls out there.
Smiling at me as he speaks. Call it a hunch but I got a feeling about you.
The rest of the evening flew by as we discussed every detail that needed discussing including a few that I'm sure could have waited. We flirted back and forth as if we knew one another for years.
Finally at some point John says we'll Jill. It's been a night I won't soon forget but I must go. You see I have a business meeting in the morning in Chicago.
Somewhat dissapointed I finish my wine and say until next time then.
How about Saturday. Maybe we could fly out to Paris for the day or something.
That sounds great to me.
Being a total gentleman he drops me off back at home. He surprised me by kissing me goodnight at the door and tells me he can't wait to see me Saturday. I felt light headed with butterflies in my stomach as John left and I entered my apartment to a waiting Lisa.

One look and I know what she's thinking as she says we'll I expected to see you a little more messed up. Guess I'll have to take care of that as we make our way to the bedroom striping off clothes.
Lisa was always the more aggressive one in bed but tonight she was very hungry.
When we got to the bed all I had on was my stockings, garter belt and bra. Her box of toys were on the edge of the bed. She broke the kiss long enough to tell me to pick one. On top was a strap-on harness so I grabbed it and handed it to her with a smile on my face.
Oh, are you sure my sweat.
Fuck me with this Lisa and do me like only you know I say while I kiss her deeply.
She lies me on the bed on my back then gets up and puts the biggest dong into the harness, then she put it on her slim waist. Turning to me she says, baby I'm gonna do you so right you won't want what's his name.
Laughing at her I tell her, well what's his name wants to share and I think it's a great idea.
She puts some lube on the dong and on my pussy not that I needed any and says your mine tonight baby so I hope your ready for me as she puts it to me pussy.
I tense up as it touches the lips of my pussy. But she doesn't take it easy at all as she shoves about half of the dildo in and holds it there.
The sudden intrusion was unexpected and as such I let out a scream as I jerked and twisted under her. Lisa just laughs at me and pulled most of it out, then shoves about three quarters back in.
I scream in ecstasy this time as I cover my mouth.
Lisa repeats this movement again an again.
I start to make a lustful incoherent babbling sound.
Lisa is really fucking my hard now. My legs spread wide, she's pounding my cunt with no mercy. My tits are jiggling hard, I'm so hot. I can feel my orgasm building as I start to think of John. I'm moaning and grunting at the same time. I can feel Lisa's pelvis hitting me as I realize she's giving me all the dongs length, but I'm feeling so much pleasure I can't do anything about it.
Lisa suddenly stops and pulled it out of my newly pounded cunt. Turn over my bitch she demands!
I turned over on my elbows and knees. Lisa takes up a position behind me and fills my hungry pussy up again. Grabbing my hips, she continues to pound me.
Who's your momma Lisa grunts out.
You are I whisper through my grunts and moans.
Louder you bitch Lisa screams to me.
You are I say a little louder.
Tell me you want me to fuck you, you whore!
Fuck me I grunt out.
Louder!
Fuck your bitch god fuck me.
I scream.
Lisa reaches up and grabs a hand full of hair and pulls back as she rams the monster further inside me cunt.
This is what it feels like you bitch. This is what a man will do to you you fucking whore. Now tell me you want more!
Please give me more, give your whore more I grunt out.
There's no more moaning. Only animal lust and grunting.
Lisa is pounding my pussy and suddenly she shoves a small vibrator in my ass and twists it while pushing it in and out.
I was not expecting the ass play but I was definitely responding to this new form of pleasure.
Suddenly I feel the orgasm that's been building within me is about to explode.
There's a sound within me that starts out really low in tone. But it's building, and in no time I explode all over Lisa and her dildo.
Screaming into the pillow as I shake uncontrollably. My ass in the air, Lisa pulling my hair as she fucks the demons out of me.
She continues to fuck me hard, not slowing at all. Feeling the punishing unrelenting pounding that Lisa is giving me. I tell her to stop. But she keeps it up saying, a man won't listen to you. Why should I.
Please Lisa I plead, through my grunts. Your hurting me!
She slows down. Then leans over me shoving it back in to the hilt and says, a man won't stop until he's finished. Then picks up the pace again, one hand full of hair and the other holding my hip. I put my face into my pillow and squeal. An animal instinct over takes me as another orgasm starts to build within me.
Lisa says, you want John to do this to you don't you. You want to feel a man inside you, don't you. To fuck you. To fill you with cum.
Through my grunts and groans I try to say yes but it comes out in the form of a sound of au gd ya.
Suddenly she pulls out and flips me over on my back climbing up to straddle me, she puts the toy to my parted lips. I suck as much as I can in as Lisa pumps my mouth full of somthing.
Suprized by the sudden flood in me mouth and throat. All I could do was swallow or choke. So I swallow.
Lisa pulls the dong from my throat as she says, good girl. You didn't spill a drop. What was that I pant. Lisa just smiles. That is a secret girly.
I love you Jill. I felt so empty But very satisfied as I roll over on my side with a huge smile on my face I purr. I love you too Lisa.
She collapsed down beside me as we fall asleep together.

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