JAIME'S JOURNEY (2/2)
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we go out again that night, with me still dressed as a woman.
"We won't go back to the same place as last night, but I think we'll be
just fine."
At that point, I was almost becoming numb to how I was dressed. We
showered, Susan redid my makeup and explained what she was doing and how
as she did.
"Before long you'll be able to do your own makeup just fine."
"Please don't make me go to work this way. Please."
"No, I'm not going to do that. This is just for when you and I go out
and take a walk on the wild side."
"I don't know how much wild I can handle."
We went to another bar, and while it didn't have the gay men and women
of the other place, no one seemed to care about two women dancing
together. We went home after and had more wild sex.
Monday morning, Susan helped me clean off my makeup and took the polish
off my fingernails. I wanted her to take off the toenail polish but she refused.
"Jaime, dear, you aren't going to take off your shoes and socks at work.
No one will know you have polish on your toenails. Besides it looks so
pretty."
That kind of set the tone for how life went for a while. Susan dressed
me up as a girl for out weekends, and I kept toenail polish on, just as
I did my panties, butt plug, and gaff. Generally when we went out, Susan
would tell any guys who approached us that we were on a girl's night and weren't looking for company. Usually that was enough to drive off most
of them. Bouncers took care of the rest. We went back to the gay bar and
hung with the lesbians pretty regularly, but not every weekend.
My boobs kept growing until I was a b-cup. I really had to work at it to
hide them while at work. I started wearing a binder on my chest while I
was there. In some ways I began to feel freer evenings and weekends when
I could just wear a bra on them.
Frequently when we were out, guys would ask us to dance. Usually Susan
would decline, but once in a while she'd suggest we just dance with the
guys for a dance or two, just to make it easier to get rid of them. Fast
dances were great, but particularly at first, I was uncomfortable slow
dancing with a guy. I did it to make Susan happy, because she did plenty
of things to make me happy.
One night we were at a club, and during a slow dance, the guy was
groping me and feeling me up all over. He grabbed my ass, my boobs, and
even down over my groin. Thank God for my gaff that made my dick
disappear. Susan told me how angry guys might get if they found I had a
dick. At the end of the dance, he kissed me and continued to grope me
until I could break away from him.
I went over to the table where Susan stood with two other guys. I'd had
a bit to drink and was still reeling from the assault on the dance
floor. As I walked up, one of them turned to me.
"Damn. That was a hell of a show on the dance floor. I almost didn't
recognize you, Jaime."
I realized the two guys were Dave and Mike from work. I was shocked and
scared. No one from work, except Susan, of course, knew I dressed this
way at times. And I was doing it for Susan, not because I particularly
wanted to, even though I was enjoying it. Hell, as a woman, I was
popular. As a guy, I was no one. Now that was all going to be upset.
"Got a good pic of you kissing that guy as he fondled you. The office
should love that."
"He... kissed me, I didn't kiss him. Please don't show that around the
office."
"You seemed to be getting into that kiss. And shouldn't everyone have a
chance to see the real you?"
"I do this on weekends. When we go out. I don't..."
"Yeah. Sure. Even on the fast dance, you were shaking that ass like
nobody's business."
"Please. I'm begging you, don't show that picture around the office."
"What's it worth to you to have us keep your secret?"
"I don't really have much money."
"There's other things you could do."
Susan decided to jump into the conversation at this point.
"Boys, this is not the place to discuss this. Let's go back to our place
and we can work this out as friends."
Dave and Mike had come out in one car, and Susan and I in another. Since
Dave and Mike didn't know where we lived, I rode with Dave, giving him directions, while Mike rode with Susan.
"You ain't much as a guy, but you're pretty hot as a girl."
I didn't know what to say. I didn't want to make him mad, but didn't
want to encourage him either. As it turned out, he didn't need any encouragement, and neither did Mike. What Dave and Mike wanted for their silence was me to suck them off and let them fuck my ass. Now Susan had
me suck off her strap on, and regularly fucked my ass with it, but I'd
never done either with a man with a real dick.
Susan told me it was blackmail and extortion, but unless I wanted to be
outed at the office, I probably needed to go along with it. I didn't
care for it, but realized she was probably right. I didn't want the
whole office to know I dressed as a woman -- even if it was only on
weekends. She said she'd try to ease into it and see if we could get
them to settle for less than they wanted.
"You know, boys, she has real boobs -- small ones, but kind of nice.
Would you like to see them and touch them?"
Of course they wanted to. Susan pulled my top off and unhooked my bra,
to let my boobs out.
"Damn, girl. You been hiding shit from us."
Dave started playing with one boob as Mike played with the other one.
Having these guys touch me kind of disturbed me, but as they played with
them and sucked on them, it began to feel pretty damned good. At one
point, I had one mouth on each boob, sucking, licking, and kissing them
like they'd never seen boobs before. I had waves of pleasure ripping
through my body as they enjoyed my boobs.
"That was nice for the prelims, but let's get down to business."
Dave stood up, unzipped his pants, and pulled out his prick. I looked at
him, and his face was consumed with lust. Mike was nearby and touching
his groin. Susan grimaced, but nodded. I edged forward and took the head
of his dick in my mouth. Dave moaned.
"God, baby. Do it. Suck that dick."
I could taste a little of his precum on his dick, as I slowly took the
shaft into my mouth until I almost gagged. I closed my eyes and
pretended it was Susan with her strap-on. At least I tried to. The feel
was different, the taste was different, and Dave moaned as I pistoned
his dick in and out of my mouth. To keep from choking on it, I put my
hand around the base of his dick and rubbed it as I worked on the rest
of it.
Dave's groans and moans became louder and more frequent until he grabbed
my head and pulled it to him. I almost choked as his dick went down my
throat, particularly when he came in a great gush right into my throat.
"Swallow it, bitch."
I didn't really have much choice. Half of it was down my throat before I
could have done anything else. Dave smiled and stroked my head.
"You're a good little dick sucker, girl."
Mike was next, and it went pretty much the same. I hoped after sucking
them off that they'd be happy and let it go. But both of them insisted
on fucking my ass as well. Dave had recovered first and unzipped my
skirt and pulled it off. He took my panties off, but my gaff covered my asshole, so he pulled that off too. My tiny dick popped loose.
"Not much there, but it isn't going to get any use from us anyhow. Cute
little plug there, girl."
Dave tugged at my butt plug and I tried to relax the muscles as he eased
it out of my ass.
"Look boys. You have to use lube. I'm not going to let you ruin her or
hurt her. And gently, boys, gently."
Susan produced the lube and Dave smeared it on his dick and around my
asshole. I got down on my hands and knees, like I do for Susan, when she
fucks my ass. Dave came up behind me and grabbed my hips. I could feel
the head of his dick against my asshole as he eased forward. It was
already stretched a bit from pulling out the plug, and he slid in pretty easily. Susan had been fucking my ass, but the flesh and blood dick felt different. He pressed in until I could feel his balls slap my ass.
"Damn. Nice to go real deep. Better than I could get with her mouth."
Dave started slow, building up speed, shoving his dick deep into my ass
with each stroke, holding my hips tight to guide it. He went faster and
faster and I almost forgot it was a guy fucking my ass, until with a
groan, he pulled my hips tight against him with his dick as far in me as
he could get it. I felt it throbbing and knew he had just cum in my ass.
As he came, so did I, squirting my cum onto the bed as he shot his in my
ass.
"Isn't that cute. The little girl came at the same time."
---------- page 3
JAIME'S JOURNEY
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62 Stories1041 Followers
Dave pulled out of my ass and came around in front of me.
"Girl, you ought to lick it clean."
I was appalled, then Susan spoke up.
"I kiss those lips. I'm not kissing shit. You want it clean, go to the
bathroom and wash it off."
Dave looked disappointed and sat down as Mike positioned himself behind me.
"If you're going to be that way, then I get another pass at that ass."
"Whatever. She's not sucking your dick after it's been in her ass."
Mike fucked my ass, then Dave fucked me again, then Mike once more.
Finally they seemed satisfied. I kind of curled up in a ball naked,
sitting up on the bed. Dave and Mike put their clothes back on.
"Good night, girls. We'll see you again next week."
"Next week?"
"Bitch. You want us to keep quiet, then you can put out."
They left and Susan locked the door behind them. She came over and sat
next to me on the bed and held me in her arms. She rocked me back and
forth for a while, until I relaxed, then gently and sweetly made love to
me. No more ass action that night. My ass had already had a workout. But
she stroked my body, caressed my boobs, then took my little dick up into
her pussy and I fucked her, before we curled up together and went to sleep.
I was nervous at work on Monday, but no one seemed to act any different,
except Dave and Mike who occasionally leered at me. Dave came by leaned
over and whispered quietly in my ear.
"See you Friday night, babe. I'm looking forward to it."
The next two Friday nights were a replay of the first one, with Dave and
Mike getting sucked off then fucking my ass a couple of times. The
terrible thing was, I was getting off on it physically, even though I
hated it emotionally. After that third week, Susan and I were lying in
bed together.
"You know there is one way to get rid of them and end this."
"How do we do that?"
"The only thing they have against you is photos of you partying, dressed
as a woman. We tell HR that you are transitioning to a woman and will be dressing that way at work. You dress as a woman at work, and they don't
have anything over you anymore."
"Go to work dressed as a woman?"
"What's worse, fucking the two of them every week, or dressing as a
woman at work?"
"I don't care for either choice, but I'll go to work as a woman, if it
means I don't have to fuck them again."
"That's my girl."
We talked to HR on Monday, and starting Tuesday, I came to work dressed
as a woman. Dave and Mike were puzzled, then angry when Susan told them
they could find someone else to fuck over. I'd been going to bars and
clubs dressed this way, so it wasn't much different going to work this
way. Most of the women seemed happy for me and I had no problems using
the women's restroom.
Everything seemed to settle back down, and Susan and I seemed happy and
loving together at home and going out together. As time passed, I found
it became difficult for me to get a hard on, or to keep it long enough
to fuck Susan. I was disappointed but we did still have a sex life.
Finally Susan decided to address the issue.
"You know, that thing isn't doing you or me any good as it is."
"So what do we do?"
"Change it out. Have surgery. Switch from a useless dick to a pussy that
we could both use."
"You want me to get rid of my dick and get a pussy?"
"Why not? You dress as a woman. You live as a woman. You can't make love
like a man anymore. Get a pussy that we can both enjoy."
"I don't know if I'm ready for that."
"We've been together for awhile now. Do this and after you're healed,
we'll get married. And I'd rather be with a woman with a pussy that
works, than someone with a dick that doesn't."
"Married? After?"
"After. You got accumulated vacation for the surgery, and I've got
vacation to be able to take care of you while you're recovering. And I
swear, I'll never ask you for anything more that you're uncomfortable with."
Of course, she had already been checking out doctors. We scheduled it
and the two of us went together. Susan held my hand as I went under, and
was holding my hand as I woke up. Even with the drugs, it hurt like hell
down there. It took two days before they took out the packing. After
they did, they told me about dilating my new vagina.
I had to start out dilating it four times a day to keep it stretched out properly, and it hurt like hell doing it. Dilation is essentially taking
a dildo, lubing it and sticking it in my vagina. The tissues there had
been totally reworked and were recovering from that, which is why
everything hurt so much. It felt weird thinking in terms of having a
vagina. No, my dick had been largely non-functional, but it was still a
dick.
Susan was with me most of the time during recovery, comforting me,
kissing me, and caring for me. I hated the dilation, but Susan and the
doctor told me it was necessary, so I kept at it. It happened slowly
enough that I didn't notice it but slowly, it quit hurting as I dilated.
What shocked me was the day I stuck my dilator in and it felt good for
the first time.
I took it slow and easy -- I didn't want to mess anything up. I eased
the dilator in and out of my pussy, and instead of the pain I once felt,
I now felt pleasure. I began rocking my hips back and forth as I slowly
and gently fucked myself with the dilator, until I leaned back, arched
my back and had a full on orgasm, like nothing I'd ever felt before.
Susan was out running errands when all that happened, but I told her
when she returned. She kissed me very sweetly and told me that while we
still needed to take it easy, we could now start to have some fun.
We both returned to work shortly after that. I still had to take it easy
and walked for exercise and to stretch all those things out. At work,
some of the women hugged and kissed me. Yeah, there were a few who were
cold, but that always happens.
We made plans for a small wedding and Susan and I went out shopping for
wedding dresses. I wore a lacy white dress, which came down just below
the knees, while Susan wore a silky white dress. I remember looking in
the mirror at how I looked, which was marvelous, but then thinking back
to the nerdy guy I'd once been. I'd gained something, but I shed a tear
over what I'd lost on the way.
Looking back, I know that Susan had this all planned from the beginning.
She picked a guy who would be so grateful for her love and affection
that he wouldn't balk at the slow steady small changes. By the time the
changes became material, I was so far along, it was almost impossible to
go back. It is done. I am who I am now, and I am hers and she is mine.
The Jaime I was before is dead. Jaime, the girl, is carrying on as best
she can.
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