Date: Sat, 16 Jan 2010 23:00:52 -0800 (PST)
From: Chuck Hughes <k56gh76@yahoo.com>
Subject: Learning to please - part 2

This is a real story; If you are not 21 or over do not go any further.  If
you do not like man on man sex go no further.


The following week was a very distressing time for me.  I had no one to
share things with - my anonymous 'sex partner', my submissive role and the
surprising thrill I got out of it, my interest in doing more, my fears of
getting a STD.  I was also tormented equally with fear of getting seriously
hurt taking anal sex, and wanting to find out if it felt good and if I was
'good' at it.

All these things I kept to myself..  They occupied my thoughts and I
struggled to focus on my classwork.  I masturbated frequently, although now
my thoughts were solely based on being the 'girl' - lying underneath
Howard's big body as he rubbed his cock against me.  Me kneeling before him
and taking his cock in my hands, using my mouth, pleasing him.  These
thoughts made me wildly horny.  For the first time I played with my nipples
and imagined his hands and mouth on them.  I loved the sensation.

Around mid week I was getting anxious thinking about the next weekend.  A
thousand questions crowded in my head: Should I call Howard?  Would I go
through with a second meeting?  Would he not want to see me?  Would I be
expected to do more things that I wasn't ready for?  Was I turning into a
full fledged fag or was I just experimenting?  Should I stop and just walk
away from all of this before it was too late?

By Thursday I had worked out enough of a plan.  1 - I would not see Howard
this weekend - I'd tell him I have too much work, or family stuff or both 2
- I would call him Saturday morning to tell him I didn't forget about him
and leave open the possibility of another meeting later.

I felt good about that.  It seemed to take some invisible pressure off me
and would give me more time to deal with all the questions and thoughts in
my head.

I also relaxed and recalled my observations from the past few days.  I was
self consciously observing both guys and girls on campus and how they
reacted to me.  I was relieved that there was no apparent change.  No one
acted any different in class or in the dorms toward me.  It wasn't as if I
had a neon "gay boy" sign over my head, and that was quite a relief.
Perhaps my secret could actually remain my secret.

I also forced myself to acknowledge two other points.  First, I didn't seem
to feel or exhibit any sexual interest toward or excitement with guys my
own age.  This was especially noted at the dorm showers which were open,
communal affairs.  I wasn't fixated on checking out all the naked guys and
I wasn't getting hard.  That was a major relief!  Second, I was really
turned on with thoughts of sucking cock, and getting fucked by a big, older
man.  I wanted to actually try these things and would need to learn more
about it.

Nowadays, every college student has a laptop with high speed internet - not
so in my day.  I spent most of Friday down to the library researching.  I
looked through the pathetically few books the school had about
homosexuality.  One book with a subtitle about "homosexual practices" was
bland and scientific - mostly about ancient history.  There were neat
pictures of Greek vases with scenes depicting gay sex, but nothing really
enlightening.  In the health section I did find a few books which mentioned
anal and oral sex - which sometimes contradicted each other.  One book said
that anal sex was medically unhealthy, high risk to disease and 'tearing of
tissue' whereas another text stated, in dry medical language, that it was a
common practice in some societies and could be enjoyable to the 'receptive
partner' under some circumstances, such as 'adequate preparation' by
manually loosening and lubricating the sphincter.

OK, that much I really knew already - I was going to have to get used to
having a few fingers in my ass.  I couldn't find anything about how to
exactly go about doing that, so I figured I'd have to try it on myself.  I
remembered Howard saying that he wasn't into "anything messy" so I figured
that if we were going to engage in anal sex, I'd be expected to loosen and
lube my ass to be ready for him.

Later, in the privacy of my room I started to play with my ass for the
first time.  I stripped and dimmed the lights in my room.  I looked at
myself in the full length mirror on the back of my room door.  My thin body
had very little hair on it, peach fuzz mostly, just a small patch of hair
at my groin.  I twisted sideways to see my ass in the mirror.  Although not
a female 10 by any means, my body did have a soft, thin look to it that
could (in dim lighting) be considered feminine.

Having no idea how 'messy' things might get, I laid a bath towel on my bed
and laid down, staring up at the ceiling.  I caressed by breasts and then
teased my nipples.  As I closed my eyes I drew my knees up and back.  I
laid there imagining a large, muscular man with a big belly climbing up on
the bed and staring down at me with lust in his eyes.  I used my pointer
finger to pull a big blob of Vaseline from a jar and brought it between my
legs.

I smoothed the lube around the hole and gently inspected the sensitive
terrain.  I started inserting my finger slowly, noticing that if I 'pushed'
with my bowel muscles the opening of my ass seemed to pucker out, making
insertion easier.  This inner flesh seemed very soft and I could liken it
to lips, or even pussy lips.  I found the whole experience very sexy and
tantalizing.  I noticed that although my cock had gone mostly soft, I was
somehow very turned on and enjoying the feeling coming from my bottom.

I knew of course that my one index finger was nothing compared to a huge
cock like Howard had.  I remember barely being able to get my hand around
his shaft - it was that thick.  Over the course of an hour I worked 3
fingers into my bottom, with no pain and nothing I thought would be
tearing.  When my fingers were inside of me they were surrounded by warmth
and elasticity.  The Vaseline provided a great gliding sensation and I
started getting hard thinking about how good that would feel to a cock.

With the position I was in, and since I was only working with my fingers, I
naturally did not get much depth penetration.  I figured the first obstacle
was being able to accept the thickness of the cock and I felt good with the
progress that was made.  My three fingers still weren't enough, but it was
a good start.

During this session I was mostly being clinical about the technique and
what I was feeling.  Once I was comfortable and enjoying the feeling of my
fingers moving inside of me, I started to fantasize about servicing 'my
man' and letting him fuck me..

When I was done I used a hand mirror and flashlight to get my first glimpse
at my lubed 'pussy'.  I noticed that the outer ring was now slightly
extended, and the edges were puffed out, with a moist look.  I absently
mindedly wondered if they'd stay that way (was I damaged for good?) or if
they'd go back.  I also noted that the 'mess' was limited to a little odor
and a few streaks on my fingers.  If this was the worst it got I figured
that with some time to clean up and prepare before a sex session, that I'd
be able to avoid anything offensive or embarrassing when I was with 'my
man'.

I cleaned up and drifted off to sleep feeling very happy with the progress
I'd made.

The next morning I went for a jog and called Howard from a bank of pay
phones in the art/humanities building.  Being early on the weekend this
bank of phones was deserted and it was perfect for a private talk.  When
Howard answered I felt myself smile and gush as he warmed to me, saying
"I'm so glad you called, been thinking about you all week.  I had a lot of
fun last week, you really seem nice and you are so hot in bed".  I had to
admit to him that I thought about him quite a bit and was really turned on
by him and everything we did.

We had some small talk and I started laying the groundwork to postpone out
next get together.  "So do you want to come over and hang out this weekend,
or go out some place?" he asked.

I told him I couldn't make it this weekend because of school work, but
maybe next weekend.  He said 'yeah, sure, OK we can try that' but sounded a
little down.  I immediately felt guilty, like I was being a tease.  "Was I
too rough with you, or too much with the 'girly' stuff - did I embarrass
you?" he asked.

"No, no, not at all - you were, you know, really cool, I liked being there,
and although you're a lot stronger than me I think you were gentle when it
counted.  You were nice and you didn't force me into anything I wasn't
ready for, you know, being like my first time with a guy and all".  I was
worried that I hurt him and needed to know he was cool with things.

"Because if the girly, prom queen stuff bothered you - we don't have to go
there" he offered.

I gulped and quietly said "I liked that too, that was fun, you know it
...kinda... made me hot"

"No" he laughed "Hot is you in a bikini with high heels on!" he laughed

I blushed and responded back with, "Oh, I see you have an active
imagination" in what I hoped was a feminine, provocative tone.  Now I was
teasing him but this felt like it was fun for both of us.

We bantered back and forth a bit, and then "Oh baby, I wish I could see
you, I haven't unloaded all week - been saving my cock for you" he gasped

"I know baby, I remember your huge nut sack and that quart of thick of cum
you gave me.  I want to be with you too but I just can't get there
now,...and I want us to have plenty of time...and not be rushed when we are
together next, that's all...  " I said with compassion, no longer thinking
like a guy, just wanting to treat him with love and respect and be good to
him.  If he truly hadn't jerked off all week I knew that he needed to get
off and I was worried that I was going to piss him off by playing coy.
"Don't you think you can hold out till next weekend? Of course...if you
need to jerk off... you can think of being with me...and me in that
bikini....and that'd be nice too..."

"Hey, it's cool -I told you that this would be no pressure.  You just need
to know that I'm really looking forward to being with you next time, seeing
your body, having you be good to me....like a woman should be..." he said.

My heart was racing and I felt light headed.  We made plans for me to come
over next Saturday morning and ended the call on a very good note.

My cock was aching in my shorts.  I was so turned on by the call we just
had it was amazing.  This big, bear shaped, strong man wanted me to be his
woman - to get him off, to gratefully work the seed out of his cock.  The
twice referenced bikini caught me by surprise.  I was positive that'd I'd
look funny in a bikini (although my cock and nuts were small, they'd still
show) and I was positive that I'd never go outside dressed that way.  But
in the privacy of his apartment...

Up till now I hadn't given 'dressing up' a thought.  As I considered it I
saw no problem with it: if it was something he wanted or needed and was
going to be cool about.  He could have been joking around, but I made up my
mind to keep an open mind about it if it ever came up.

I was also glad that I had the strength not to tell him about my ass
fingering the night before.  I wasn't sure if during the next week I'd be
ready, but if I was ready to get fucked I wanted it to be a surprise for
him.  I also didn't want to set expectations that I couldn't follow through
with.

That week I kept up at my studies and worked overtime to get readings and
projects done so I could head into the weekend with a clear conscience.

I also worked on my ass further.  I picked up a few cucumbers which seemed
a little smaller than I remembered Howard's cock and practiced getting them
into my bottom.  At first the cucumber seemed very big and intimidating,
but with 1, 2 and then 3 finger prep my rosebud was ready.  I found out
that I needed to switch positions - on my knees, knees spread wide apart,
face down on the mattress.  My one hand holding the cuke went between my
legs, the other holding one of my butt cheeks to the side.

Getting the full width in the first time took some effort, but fortunately
no real pain.  Once I had it in and seated well up inside me, I practiced
with different positions, moving very slowly and getting used to it being
in me.

After these sessions I'd inspect my rosebud and notice that it was always
soft, puffy and distended - it looked fuckable and ready for cock.  I also
noticed that a few hours later it would seem to have sprung back to it's
original shape and dimensions, which was a relief.

I felt as if I had learned how to go about loosening myself to receive anal
sex.  I was very horny to try to be a good receptive partner.  I was very
turned on by Howard physically and had a good feeling that I could trust
him to be gentle and cool with me in a vulnerable position.  I was ready to
get fucked.

I hadn't forgotten about his STD comments either.  In further preparation
for Saturday I went to the drug store and picked up a package of latex and
non-latex condoms for him, and a small tube of lube for me.  I wanted to
have everything and I remembered the lube he used on my the last time was
thin, and I wanted something thick like the Vaseline I was used to.

Friday night I remembered to eat a light salad for dinner to help clear me
out - I was self conscious and wanted things to be as clean for my man as
possible.  Saturday morning I likewise only had fruit and juice for
breakfast.  I took extra time cleaning myself 'down there' and 'back there'
- knowing that in an hour's time I was going to be spread open and
receiving a man's cock in me.

I also took care to masturbate twice on Friday and twice Saturday morning.
I wanted to focus on Howard and did not want my small boner getting in the
way.

I left campus with lube and condoms in my coat pocket and butterflies in my
stomach.

End Part 2