Date: Wed, 5 Jan 2011 10:26:23 -0800 (PST)
From: John Smith <fire8743 (at) yahoo (dot) com>
Subject: Fw: Climbing the Mountain Ch 3

Climbing the Mountain

By Skybear   fire8743 at yahoo dot com

DISCLAIMER: This story contains descriptions of explicit sexual acts of a
man/boy/girl lust/love. It contains graphic scenes of sex between an
underage boy and adult male.

...If this type of content offends you or you are under the age of 18 doing
not read it.

Author's Note: This story is the property of the author Skybear. It can be
downloaded for personal reading pleasure or sending to a friend, but cannot
be reposted. If it is illegal to read such material where you live or if
you find the topic undesirable, then please leave now.  If you enjoy the
story, please let me know.

Your comments are highly encouraged and appreciated. Fire8743 at yahoo dot com

I suggest reading Chapter 1&2 so you can get the progression from complete
virgin to now.

Chapter 3 Graduation.

After graduation from high school Anita and I were married but I managed to
keep my friends on the side as was done back in those days. The closet was
locked, besides I was BI sexual not just gay. Soon after, Brent was married
and his wife had a son. Don was still in the picture and I think Brent was
Don's one true love.

The Air Force accepted me just before finishing college with the
understanding I would complete my EE degree. Here I am second louie, and
for the first time my bubble was busted. The AF found me unfit for fighter
school because I was too light weight to be the bad fighter pilot. The real
reason I even got into the Air Force was because I had college, a
commercial pilot's license and they needed B52 bomber crews for Vietnam
fodder. So off I go to the Strategic Air Command and trade my single engine
Cessna for 8 engines and a load of bombs. OK I am still flying and getting
paid to do it, no real harm.

 Married less than a year, Anita could not put up with my military duty and
filed for divorce... OK by me, what the fuck. No kids I had to worry
about. Meanwhile Paul enlisted as a mechanic in the AF and Don and Brent
would write about every two weeks, I knew where real loyalty was.

Ya probably noticed sex took a back seat during this period but I managed
to keep the shaft lubed with a few one night stands with girls but the itch
for male companionship was still there.

Orders came and I was to be stationed at Barksdale AFB in
Louisiana. Arrived on time and outfitted with flight gear and had the
obligatory flight check that was passed with flying colors. This is great,
close to the old home place and my friends. The Air Force found out that I
was NOT UNHAPPY and issued orders that our crew would fly a B-52 to Utapow
Thailand for 6 months Temporary duty, dropping bombs on those deemed to be
a threat to our country and dogging the surface to air phone-poles that
were designed to ruin our day. (Several close calls) Thailand was a great
place to visit but I had to stay cool less someone notices my off duty
choices. Still it was nice to get a massage, blowjob and a fuck for 5 bucks
including tip. Some of those girls were very young and let's, say
enthusiastic.  I requested permanent assignment back to Thailand when our
TDY (Temp assignment) ended and we flew back to Barksdale. This serving in
the warzone enabled me to move up in rank and shortly after my return to
Thailand, command pilots were hard to get so I moved up to my own aircraft
& crew. (This was the time bombers were being shot down by the little short
bad guys).

 In Bangkok on one of the few off days I managed to slip away from the
crowd and found a sissy boy. This was my first introduction to a real
pre-op transvestite. She was gorgeous from head to toe with real titties
and a curvaceous little ass but the smallest of cocks. This is person that
was simply born in the wrong body. Thinking back, on how she could suck me
for so long was amazing. She would bring me to the peak and back down so
many times and had finesse with fingering the prostate I never found
again. All day of massages, sex with several happy endings & tight asshole
that would suck you in. The next morning you would have thought I gave her
all the gold in the country when I produced two American twenty dollar
bills. Now I had a connection. Pictures of her and me out on the town are
in my private scrap book, I wonder what became of her!

The AF was rough on gays but most of us managed to stay below radar and out
of known gay spots but still stealthily meet up.  One such person was
Col. Davis, (this name was changed, not because he was innocent but he is
still alive) commander of the maintenance squadron in Thailand. He was
getting some flight time on a milk run back to Barksdale AFB in Louisiana
for exchanging planes and we would return to Thailand in a week. In a
layover we shared a room and managed to get quite drunk, staggering back to
the room from the bar, remember we had been overseas for 7 months and
needed the rest.  Bill got to the room and said he needed a good massage
with a happy ending like you could get at the Fascination bar outside
Utapow in Thailand. Well I knew that was notorious for gay massage and was
surprised he said something. I laughed and said I was just drunk enough to
give him the massage. "Then do it captain or shut the fuck up, that's an
order" I gave him a great massage with a very happy ending as "ordered" We
both woke up with hangovers to beat hell, and stayed friends for many
years. He retired as a damm General so I guess he was able to "don't ask
didn't tell".

 One thing about Bill was he had the longest and hardest cock I have ever
come across. We would go into Bangkok and pick up a couple of young working
girls. Once they saw him hard, they knew it was going to be a long hard
night. But he was very gentle when we shared a room by ourselves, no way I
could take him all the way down my throat but I tried. Actually I would
rather have him fuck me and rub my dick at the same time. He seemed happy
to handle this chore.

By this time Paul and I had drifted away, he was married and had kids,
still he was my first fuck buddy but we never spoke of our escapades again.
Once the war ended I saw the need to leave the AF for civilian life as a
design engineer for Wang Labs. Boston was a hell of a place for a single
guy that would swing both ways and it was still the 70's.

I made several long lasting friends in Boston and one girl is at the top of
the list. I knew she was a little butch on our first date but I did not
realize how much until close to Halloween when she dared me to switch
roles.  Since I was still skinny as a rail, I dressed in a little black
dress, complete with long red hair wig and a skirt split up the side,
shaved legs of course. She knew something was up as I was happily putting
on stockings, garter belt and panties at her place and because I was hard
as a rock and had a wet spot on my new panties. Plus I knew how to put on
the bra and falsies so easily. Pam started to laugh but said you really
like this don't you. I said it is invigorating, so we made love before
going out on the town. This was the first time I had loved a girl while I
was wearing female attire, of course Pam had on male type clothing, my
socks, tidy-whites and one of my ties. She climbed on top and proceeded to
screw me, feeling up my new breasts and rubbing my legs, like she was the
MAN and I was the girl. Another step up the mountain completed...

She dressed in a three piece suit with hair tucked under her hat and a nice
bulge like a cock courtesy of a pair of my socks. Really, she looked like a
cute guy, even produced a wallet for her back pocket and paid for
drinks. We went out on the town and wound up on that famous street and
inside a bar known for the gay/lesbian crowd. We met another couple but
both of them were dressed as women. He was really nervous and kept looking
around like someone was going to recognize him. I suggested we dance and he
reluctantly agreed after some urging from his wife, I think he did not look
close enough in the dark to see I was a male, cross-dressing. Out on the
dance floor it was really crowded but we slow danced and I felt up his cock
which was becoming very hard. He reached down and rubbed the front of my
dress finding a bulge he jerked back for a second, SURPRISE.

After a few drinks he finally relaxed some and we talked as I put his hand
under my little black dress, I think he liked what he found but was
somewhat rough in handling my cock.

Pam and Linda danced a few dances then went to the ladies room and when
they came back Pam whispered "would you like to go with them?" I nodded
then she said "Linda wants to be with me, are you ok with that?  I nodded
again. How about you being with him? Another Yes. Now I had never been in a
situation such as this before. Pam & I kinda came out at the same time to
each other.

After more drinks and dancing, off we go to a hotel close by as Linda and
Hubby were from out of town. Inside Pam and Linda literally jumped on each
other kissing and tearing off clothing. I did not even remember his name
but he planted a big kiss on my red lips and I, being the woman, opened my
lips for his tongue. My hand lifted his skirt finding panties which had a
lot of lace and was very wet in the front from his precum. I could not wait
to get out of my dress and feel his hard dick. But he took control like he
was the man; I managed to get his skirt off and sucked his cock through the
silky panties causing him to moan loudly. We more or less fell on the other
bed as I felt his large balls then pulled his panties off to see my
prize. It was about 6 inches, fat and uncut. As I went down on him I kept
the foreskin on top of the head just for fun. He kept reaching down to skin
it back but I pushed his hand away as I knew he would finish too fast. As I
massaged his hole which was very tight he submitted to my finger in his
ass..

The girls were into each other, really moaning and groaning with ecstasy on
the other bed. Hubby and I were now in 69 positions and exploring each
other. I eased another finger into him and felt him start to panic so I
backed off the finger but would not let him cum. After a few minutes I was
again massaging his hole with Vaseline and managed to touch his prostate
which sent him into orbit and he almost sucked the head off my dick. I
pulled out from under him and massaged his ass but told him to slow down we
had plenty of time. By now he was really enjoying the milking as his dick
was seeping a large amount of liquid. I realized he had cleaned out before
dressing so that was my clue this guy wanted to screw.

 I whispered have you ever screwed before? He choked up and shook his head
no, but I told him it would be great & I would go slowly.  By now he was
really nervous and had lost some of his hard-on but he was enjoying the
touching of his g-spot. I rolled him on his side and placed my cock at his
opening and just kept whispering to him to push and slide back. When the
head popped in he jumped and said it hurt badly but I kept him calm. Linda
and Pam had finished and joined us on our bed, Linda laughed and said
"virgins do hurt the first time baby, but it gets better". He took a deep
breath and slid back letting me get my cock at his pussy but this time I
held onto his hips so when the head popped in again I made him just stay
right there and breathe deeply. Linda was kissing him hard and taking his
mind off the pain as I eased in and out slowly until I was balls deep in
his ass. Pam was wide-eyed seeing a man become a non virgin for the first
time. I needed to nut very badly but wanted him to come first. Linda slid
down and took his semi-hard dick in her mouth and made him cum buckets. I
could feel his muscles contracting around my dick knowing he was being
treated to something he would never forget. Welcome to the mountain newbie!

We dressed again and went to the café downstairs; His name I found out was
Robert. His wife had been BI-lesbian for years and Robert had tried one or
two men but only by receiving orally. They had talked openly and agreed to
expand his horizons over the Halloween weekend and we were the lucky
ones. Remember Robert and I are still dressed and in makeup at this hotel.

Pam and I met them again a few weeks later for more fun. Pam and I
purchased the first strap-on I had ever seen from a seedy xxx theater in
the bad side of Boston; actually we bought two, one for Linda. (Remember
the internet was unknown at this time) During our second meeting we went
out to dinner then a show with Pam and I switching rolls again, I was in
drag and still thin, looking almost good. Robert could not pull off the
dressing part, but he wore stocking and panties under his pants. After the
show we went to the same hotel downtown. Pam and I got a few looks in the
elevator but we did not care. Inside the room Pam was smooching with Linda
and taking off her clothes, Robert and I just watched them while rubbing
each other. Pam was obviously the man in this picture. I wanted to see Pam
take Linda with the strap-on and Robert was just as intent watching as I
fondled his cock.

Linda opened her legs as Pam still in my underwear and with the strap-on
rubbed up and down Linda's slit before easing into her pussy. I noticed how
careful and easy Pam was being to her lover that obviously wanted that fake
cock deep. Robert and I got into our own thing as I enjoyed taking him in
my mouth, licking the head and rolling his balls in my hand. He removed my
cloths as a man should do his lover. Once again I did not let him come but
got on my hands & knees offering my boy pussy to him. We had talked about
it on the phone but he was in such a state of lust it was Vaseline and one
swift motion balls deep in my ass. If Pam and I had not been playing with
the strap-on I would have been in severe pain, but that's a man for you. I
looked at Pam and Linda who were watching us very intently now as I stroked
my cock while Robert was going for broke and would not last very long. Once
he was finished he pulled out and flopped on his back. Pam and Linda
started laughing, Robert seemed offended about the laughter until I said
"that felt good but now I feel empty and un-loved"

  We had a couple of drinks just enjoying each other when I started to rub
Robert and get him hard, then I whispered" MY TURN" and proceeded to slam
fuck him with a quick cum and pulled out" He sat there for a minute before
saying " I see what you mean about too quick & feeling empty" Linda came
over and said " before you were just being a man, now you know how it feels
to be a woman for a change"

Pam gave Linda her present, their strap-on dildo, and we listened to Linda
squeal with delight, telling Robert "you're gonna get now girl" Pam and
Linda immediately tried out the toys on Robert and I.  The girls were so
easy and sensuous as they took us both at the same time. I must admit I
enjoyed the side by side experience & playing with his cock.

 We enjoyed teaching Robert how to be patient and gentle for the rest of
the weekend. I am still friends with them today, although we have not been
together since the birth of their first child. Robert still loves silky
things and Linda likes the occasional romp with a butch type.  Another step
up the mountain.

Boston only lasted 12 months as I realized someone else was collecting the
big paycheck for my thoughts and labor, besides, I was only slow flying a
puddle jumper and wanted something better, faster, aerobatic and mine, not
a trashy rental plane.

Pam and I decided to marry and start our own computer company just outside
of New Orleans. (This was before the "garage computer" came on the scene)
Back in the home area I picked up with Don but he was more interested in
the very young boys. Brent had moved away to find work in the just
starting, satellite business but stayed in close contact with Don and me by
ham radio.

Personal computers were soon to arrive. Life was good and our education was
to take a turn toward Swinging and BSDM.  Guess who was the first Sub?

Continued: