Date: Sat, 17 May 2014 23:54:17 +1000
From: Colin Barnard <crkbarnard@gmail.com>
Subject: Enjoying Myself Part 15

This is the last installment of Leo. So I started my "4th Year" at
secondary school (is that year 11 in today's language?) with Adrian but
that fell apart and by the '5th year' had discovered Leo. Towards the
middle of that year I was to start activity with another boy that would
last until I went to Uni but I will go back to Leo even though by now it's
late in the "5th year" and things were well advanced with the other boy.

Leo had a girlfriend and so, inevitably, our sessions almost stopped. He
was still a horny teen and would, on the odd occasion, come back to my
place at lunchtimes but never at weekends. This weekend, however, he was
due to go to some soccer tournament so on the Friday night he asked if he
could stay at my place because his parents couldn't drop him at school,
early Saturday morning. I was happy with that.

Friday evening we played computer games in my room and it came to the point
we needed to go to sleep and for some reason I thought he was in a funny
mood so didn't push the idea of a wank. Instead I decided that I would just
start wanking myself and see if he took the bait. I got a porno mag out and
started to slowly knock one out. Within a few seconds he asked if he could
borrow a porno so I passed him one. As we were on separate beds I couldn't
initiate a mutual handjob and I wasn't certain he'd be up for a proposition
of a bj, given his funny mood so, instead, I was just content to catch
glances of him bashing the bishop as I wanked. Within a few minutes he
looked across at me and half-whispered, half-gulped "You ever done it up
the arse before?" My mind leaped. "No" I replied, defensively, not knowing
why he was asking me. There was complete silence. After what seemed like
hours but was probably a few seconds I croaked "Have you?". "NO!" came the
rapid and definitive reply. I wasn't sure where this was going but I had to
explore further. "Why did you ask? Do you want to?" I trembled, terror
clear in my voice. "No way." he declared firmly, followed by a short pause
then a suggestive, "Why do you?"
I thought about it. Was it a trap? We hadn't done anything for a few weeks
now and I was getting my kicks elsewhere. I did NOT want a repeat of the
Adrian situation.
"Erm, I don't mind." I said, equivocally. "Is that a yes, Charlie?" I
replied that it was.
"Okay, do you want to come up on this bed, or shall we do it down on
yours?" he asked in a matter-of-fact manner. Wow, I thought, this was ON!
"Up on yours?" I suggested. "Fine" he replied.

And so I got up and excused myself to go to the bathroom. After the 'dirty'
incident with Adrian, I needed to ensure I was clean 'down there' and so I
managed to sort myself out and returned with some baby oil from the
bathroom cabinet. To my surprise he was lying on his back and had put a
condom on. "Jesus", I thought. He was more prepared than I was expecting.
Had he planned this or did he just carry condoms with him? This was not a
trap, or if it was it was a highly elaborate one.

I suggested we turn off the main light and put on the bedside light. He
agreed. I then got up on the bed and sat across the top of his legs,
fondling his balls and trying to massage his dick. It was my first
experience of being with someone wearing a condom so wasn't totally sure of
how I could stimulate him and get in the mood before doing the inevitable.
I got on my knees, legs either side him and tried to give him a blowjob.
The taste of the condom was disgusting and, what's more I didn't really
know what to do and it wasn't going well. I could see he looked impatient
and the prior attempt at being penetrated by Tim had not gone well so I
didn't want to ruin the opportunity by making a false move. With a sense of
determination, therefore, I greased up his rubbered pole with baby oil and
squatted above him, thinking I would sit on his dick. I had no idea if that
was going to work but around this time I had been starting to experiment
inserting a carrot in my butt and knew that it was going to be easier to
get in that position. Leo looked happier that I was now going to commit to
this. I honestly think he thought (and prob thinks to this day) that he was
the one out of the two of us that wanted this more.

As I lowered myself down, the tip of his, now, rock hard dick came into
contact with my hole. This was it, there was no turning back. As I
continued to drop down, I felt his dick suddenly lurch and skid up under my
balls so I readjusted and made a second attempt. This time, the tip hit a
tiny bit further back and I could feel it starting to stab at me. I tensed
and recoiled somewhat. "What's wrong?" he asked, clearly not understanding
how much this was likely to hurt. "It's okay - I just need to relax a bit"
I reassured him. I had learned this from using a carrot on myself. I then
went again, lowering myself back on to his dick. He reached forward and
started to massage my dick in his hand, back to full mast. As he did so, I
started to feel myself relax and so I pushed down further. As it started to
go in, I felt another sharp pain and winced. "You okay Charlie?" he asked.
I could sense he was going to give up so with the sentiment of ripping off
a Bandaid I then plunged down, the whole thing sliding like a savage weapon
into me. "Oh fuck" I exclaimed. My whole weight now on Leo, I just sat
that, steadily trying to acclimatise to him being inside me. I wanted to
get it out of me so badly but was terrified that his dick would be dirty
and get he'd get freaked out. So I just sat there for a while. Looking back
it was quite comical.
Leo noticed I'd gone almost limp and as he looked at my dick, I too
realised that I was at half mast and so teased myself back to full hardness
again. As I did so, things started to feel different. Before it felt
uncomfortable and I felt 'full'. Now I thought of him being inside me and
this turned me on immensely. "Okay Leo, I'm ready now." And he started to
pull down a little and then up. It hurt but it wasn't a bad pain - it was
actually not bad. He was VERY gentle and it probably wasn't even going in
and out by more than 5cm. He started to build up a rhythm and I was now
enjoying myself enough that I stopped wanking and just felt him move inside
me. "Charlie, my legs are going a bit dead. Shall we do this doggy-style?"
he suggested. I too was a little uncomfortable (I was literally sat on him,
legs either side of his body - basically my full weight on him). As he
pulled out of me I got that sensation that I had experienced with the
carrot - that incredible feeling of something sliding out of you. I looked
down and his condom was clean. I was relieved.

I got on all fours, as instructed, and lowered my head. He took a few
moments to position himself behind but was soon at my hole and pushed
forward. This time his dick entered me with almost no pain this time. It
was in and he pushed right down to the base of his dick. I felt him
stirring deep inside of me and for the first time I was really starting to
enjoy this. He pulled out slowly, then thrust back in again and back out
and so on very, very slowly. I moaned quietly, "You can go faster if you
want",  turning around to look back at him. He had taken his glasses off
and looked much more hansom than I'd ever seen him before. He was smiling
at me and had a sense of purpose. He was in complete control. It felt
incredible. They say pain has no memory and maybe I was in more pain than I
am now recounting but I remember the thrill of being taken by another man
(or boy in this case). He stepped up his pace as instructed and really
started to screw me now. He was grunting heavily and repeatedly saying "oh
God, mmmm, ahhh, oh God" as he quickened his pace. He was enjoying this
just as much as I and I was stroking myself as he abused my hole. He then
started gasping and breathing out very heavily and stammered "I'm cumming
Charlie" and pulled me towards him, thrusting himself deep inside me. I was
wanking furiously by now, hoping to synchronise our orgamsms. He stopped
moving and I could feel his dick pulsate against my hole as he pumped his
spunk inside of me, captured by that condom. I was getting close now and as
he pulled out, that incredible feeling of his cock quickly sliding against
my sphincter tipped me over the edge and wave after wave of my cum sprayed
from my teen dick, all over my quilt. I was completely weak and, removing
the soiled quilt, collapsed on the bed, feeling dirty, slimy and..... very,
very satisfied. It wasn't my first anally-stimulated orgasm as I'd wanked
myself whilst I had a carrot inside me but it was the first time someone
had used my hole and climaxed inside of me. I loved every minute of it.

Leo had already got off the bed and was ripping his way through half my
tissue box and wiping the baby oil from his legs and from around his balls.
He asked me what we should do with the used condom and tissues and what we
should do about the quilt. I said I'd flush the toilets and condom down the
toilet and get a new quilt cover. I headed off to the bathroom in my
dressing gown and learned something that day: condoms are very hard to
flush! It eventually disappeared. By the time I returned Leo had removed
the quilt cover and handed it to me in exchange for a new one. He said we
should turn off the lights as he needed to get up early for the football
tournament and quickly did so. Within a few minutes he appeared to be sound
asleep. I was so tired but excited. I managed to climax another 2 times
that night and by the time I woke up Leo was dressed and opening my bedroom
door to go. "See you Monday morning" he said in a chipper manner. "Good
luck in the tournament" I added and with that he shut the door and let
himself out the house.

Over the next couple of months he screwed me two more times - basically
when his girlfriend was on her period. At the end of the school year his
family moved to Edinburgh and I didn't see him for another 2 years. I'd
just passed my driving test and went to see him. That time I arrived very
late on a Friday night. His parents had gone to bed and his was waiting up
for me. I was sleeping on a spare bed in his room. I think we waited all of
2 minutes before he was knelt behind me and pushing himself at my hole
again and maybe a further 5 minutes before he was grunting and piling his
load into me.
We lost contact and then, maybe 10 years later we got in touch via FB and
circumstances brought him to the city where I was working. He was married
to his second wife and had a prior failed marriage and a child behind him.
Nothing was mentioned that evening but I was dying to talk to him about
what we'd done. A little while later he was back in town for a training
course and called me to see if he could stay at my place to save money.
After a few drinks and a couple of joints he brought the subject up of how
a few of us went back to my place for lunch and that it seems odd now that
we'd often wank. He knew I was gay and I was surprised he was prepared to
talk about it. He admitted that he'd once, since, had a gay experience but
that he and his mates were generally pretty homophobic and that if they
knew about his past they'd probably desert him. I assured him that some of
them, too, would have 'experimented' as horny teenagers.
To cut a long story short, he ended up initiating sex with me and went
immediately to blow me. He'd clearly never done it before because it was a
bad effort and there were too many teeth involved and I had to get him to
stop. I asked him if he'd fuck me like he had when we were 15 and that time
in Edinburgh but he said he didn't think he could do that again so I blew
him for old times sake. Strange that he was prepared to blow me but not
screw me when my experience has been that straight guys tend to be able to
fuck guys, kidding themselves that it is just like screwing a girl.

So that leaves me to write up about Dean. Thanks for reading my journey and
holding in there as I've replayed these memories.



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