From: Betty
Date: Fri Jun 22, 2001 12:06 pm
Subject: My first "date"

Hi

I had my first "date" last night and it was great!  I didn't want to do it.  I
did not feel at all ready, but Sickman made me.  Well, he didn't force me, but
he told me that he knew best and asked if he had not been right about
everything else, which he has, and that it was time I started living my new
life not just moping about the one I lost.  Which isn't fair because I really
have not been moping, at least, not much.   But anyways, he'd already gone
through all the e-mails I've been getting and found one he thought would be
suitable, and set the thing up.  He wrote to the boy, found out about what he
was looking for and told him what to do.  It was a boy who goes to the school
my son used to go to.  It seems that Erin sent my e-mails to some of her
friends and by now the whole school has read them.  

Great.

Anyway, this kid wrote last week and went on and on about how much he liked my
e-mails and that he wished he had a mother like me because he had fantasisies
about it, too.  When Sickman wrote back and said that I might be willing to
meet with him for a date, he got him to describe his fantasies in more detail
so the kid wrote this story about how his mother catches him masturbating and
basically becomes his personal whore because she thinks that masturbation is
bad for his self-esteem.  So Sickman -I wish he would give me something else to
call him, I feel like I am talking about a superhero or something - anyway, he
told the guy that I would make his dream come true and basically wrote a script
for the whole thing.  

The kid - oh this is silly, I will call him "Richie" - Richie showed up after
school, buzzed me to get in the building and then let himself into the
apartment as if he lived here.  He is a skinny, pimple-faced redhead.  He is
only seventeen, and he looks it.  My first thought when I saw him was "I can't
do it."  I mean, he really was just a kid.  Well, I guess he really isn't any
younger than Chris, but well, maybe it was just the shock of seeing how young
he was.  And somehow, the pimples made him seem even more like a kid.  

Anyway I managed to play my role alright.  I was wearing a nice, "mom" sort of
dress and an apron, and I had some cookies baking in the oven.  I gave him a
big hug and asked him how his day had been.  It all felt very silly and
contrived, but Sickman had given me my script and I felt like I had to try to
stick with it if only because if I had not I would not have known what to do. 
He managed to say his day was fine; he was obviously as nervous as I was.  I
was then supposed to tell him to go and have a shower.  Sickman bought a new
shower curtain yesterday that is basically clear with white stripes.  

So after I heard the water running, I was to go into the bathroom on the
pretext of bringing him the towels which I had removed earlier, but I got to
look at him through the plastic.  Did Sickman think that this was supposed to
turn me on?  It didn't.  All I saw was a skinny teenager standing in the shower
looking awkward.  He obviously was as unused to being naked in front of old
women as I was to having a naked boy in my shower.  It was so awkward that I
was glad I had been told what to say.  

"Let me soap your back, darling"  I said, pulling back the curtain.  And
immediatly started getting sprayed with water off his body.  But I soaped up my
hands and started washing him like I was supposed to and it wasn't long before
the feel of his slippery skin and the perverseness of what I was doing started
turning me on.  And him too; when I had him turn around he was obviously
embarassed to have a solid erection wagging obscenely in front of him.  But by
now I was starting to get into my role a bit more and managed to tell him, as I
soaped his chest, not to be ashamed of it, that young men often get erections,
and that he should be proud of such a nice, big cock.  Which was true, it was a
very nice one.  At least, I certainly found I could not take my eyes off of it.
 I took my time washing both his legs before I actually soaped his cock and
masturbated him a little, not too much because I did not want him cumming yet. 
When he groaned a little, I stopped and told him he could wash his own hair.  

"Oh my," I said on queue, "Your clothes got wet.  I'll just go put them in the
dryer.  I'll bring you some cookies in your room when they're ready."  So I
quickly mopped up the worst of the water from the floor with one of the towels
and then took his clothes down to the laundry and put them in a dryer with the
soaked apron.  

By the time I had putted the cookies on cooling racks and changed my dress I
figured he had had enough time masturbating in Chris' room and steeled myself
for the next round.  Carrying a tray with milk and cookies on it, I opened the
door to Chris' room and tried to look shocked when I saw him sitting on the bed
in nothing but a towel, masturbating while he thumbed through the stack of sex
magazines that Sickman had placed half under the bed.  

"Richie, what are you doing?!" I said, quoting the mother in the story he had
written me even though it was quite clear what he was doing.  He froze, his
hand gripping his hard cock.  Seeing him like that, knowing what I was going to
be doing, was very exciting.  Suddenly I didn't feel turned off because he was
a skinny young kid, but turned on.  He was stammering, unable to remember what
he was supposed to say next, even though it was his fantasy we were
re-enacting.  I knew I ought to be helping him, but I kind of liked watching
him look embarassed, his cock wilting in his hand, caught sitting in a sea of
open porno magazines, surrounded by naked women.  

Finally, I had mercy on him and helped him out, saying that it was okay, and
that it was perfectly natural for young men to be curious about sex and then I
couldn't remember any of the rest of the silly dialog we were supposed to have
so I just jumped straight to the end where I tell him that masturbation is bad
for his self-esteem and that I would take care of his sexual needs from now on.
 Then I set the tray down on the bed side table and told him to enjoy the milk
and cookies while he read his magazines and that "Mommy" would take care of his
needs.  It was all very improbable and only vaguely what he had written, but he
did not seem to mind once I went to my knees and started fondling him.  I tried
to go slow, but he started cumming in my mouth almost immediately.  

"Thats a good boy," I said as he pumped the last few squirts out to run down
over my hand.  "Isn't it better to have Mommy do that for you then to do it
yourself?".  

He agreed that it was.  

"Oh-oh, you made a mess here.  Let me clean that up for you", I said and went
back to work carefully licking up all the sperm, sucking it out of his pubic
hair and licking his balls far more than necessary.  I told him he could lean
his magazine on my head, as he had in his story, and between my licking and
looking at his porno, he was soon hard again.  

I wasn't sure what I thought about all this.  On the one hand it turned me on
to be sucking that boy;  I started playing with myself after a while.  But it
really did not feel good for him to be looking at pictures of other women,
women who I know are younger, more beautiful, more shapely and just a lot
sexier than I am.  I felt like he did not even care about me, like I was
nothing but a mouth.  Which is what I was, but I did not like feeling that way.
 I also felt really perverse to be doing it in Chris' bedroom.  I kept thinking
what he thought of me and what he would think if he saw me then.  But mostly,
it was hearing the pages turn, knowing that he he was more interested in those
women then me. Sickman says that I enjoy being humiliated, and I know that he
is right, but I did not like this feeling.  Maybe there are different kinds of
humiliation and this was the wrong kind.  I don't know.

Its like when I went for my job interview the yesterday.  I went all dressed up
with my resume all ready expecting to have to answer questions about my
qualifications.  Except the only qualification he cared about was whether I
would suck his cock.  The first thing he did when I sat down was open a
filefolder on his desk and started looking over printouts of all my e-mails
sitting as if it were my resume.  I know I turned scarlet.  I felt so stupid
sitting there with my stupid resume in my hand, as if he cared about my job
history.  He asked if I had written all those letters and I don't even think I
could answer him.  I think I just nodded.  Then he asked me if it was all true
and I admitted it was.  Then he said he had a number of business friends who
might be able to use a woman of my qualifications if I REALLY wanted a job. 
"How badly do you want a job?" he asked, but his look said everything.

So there it was.  He would help me find a job if I was willing to suck cock.  I
know that is what I had said I wanted, but somehow, now that it was being
forced on me, it did not seem that exciting.  It was insulting.  I don't know
why it didn't work in real life, but it didn't.  I felt like he thought that
that was all I was good for, and that he was taking advantage of me because I
needed the job.  Its so stupid, because that is exactly what I have been trying
to get men to do to me for months now.  But that was always my idea, so it
wasn't real, and this was.  Too real.  He was sitting across his big desk
grinning at me, waiting to see "how badly I wanted the job".  I think the worst
thing was how smug he was.  As if he was so cleaver to have me at his mercy. 
And the thing is, I was.  I DID need a job, and fast.  My husband has cut off
my child support no that my son has left so I really was quite desparate and
with that in mind, I swallowed my pride and admitted "Really badly".

"Why don't you show me how badly...".  I felt like crying, but I went around to
his side of the desk, went down on my knees, and did it.  I felt totally used
and degraded, but I did the best job I could for him.  And it did start getting
to me after a while.  Just the thought of actually being forced to suck that
rich old businessman just so he would help me find a job.  It made me feel
totally pathetic, but it turned me on, too.  Maybe that's the thing both with
the interview and with "Richie": I feel horrible about it but I get off on it
at the same time.  I just don't understand how I can get excited by something I
hate.  Does anybody who's getting this understand it?  Let me know.

Anyway, to finish off with "Richie", after a while I did start getting into it
and started masturbating myself while I did it.  Sickman says that any guy I
blow already knows that I am a dirty whore so I should not feel any more
ashamed to be playing with myself in front of him.  I guess he's right, but he
sure has a way of putting things.  Anyway, I got into it more and more and
started talking between licks, asking if "Mommy" was doing a good job for him
and did he mind that his mommy was a dirty slut.  He put away the magazines
then and we locked eyes while I sucked and talked until he came again.

I told him he could come over again sometime.  The only problem is that I am
getting more and more e-mails of guys wanting dates.  I don't understand how
everybody is finding out about it, but I can't begin to even write back to
everyone.  Sickman says he is going to be my "whoremonger" and that I am going
to be sucking so much cock that HIS jaw will ache just watching me.  He called
while I was writing this and I told him all about last night.  He said he
thinks I am ready for a little party and wants to have it on Sunday.  God, I
told him okay, but I don't know if I AM ready.  I guess I just have to trust
him.  So far he has been right about everything even when I doubted him.

Oh yeah, and I also am supposed to go over to my manager's father's office
again this afternoon supposedly to find out how he did on finding me a job but
he will probably want another blowjob, too.

Like they say, "Be careful what you wish for"


Betty