Date: Sat, 2 Dec 2023 14:52:33 +0000
From: none of. yourbusiness <jhenry922@hotmail.com>
Subject: Teacher then cruising

After that first boy I had sex with, first time on a sleepover oral sex
and then oral sex after school on a regular basis that ended after he
moved away before the start of summer.

 The teacher came into my life a few weeks later. I had gotten ot to use
this school's computers in the Annex Building, a privilege given to me by
my parents friends the principal but I had to keep my nose clean during
the week and if I did I got the key on a Friday to use until Monday
morning. That's where I met the him

 I had sex with him a bit intermittently at first until we figured each
other out. He was 10 years older than me, a bit taller a bit heavier and
a bit more hair than me but I had virtually none at the time.

Sex sort of came and went as we were both busy with our lives, him with a
new classes that he had to teach, and me with friends and activities
outside of that school annex building. If I knew I was going to be in
there on a Friday afternoon or the weekend, I would phone his house and
let him know that I would be using this space. I made it sound innocuous
so I like I didn't want to disturb him if he was marking papers or stuff
like that. If I actually got him on the phone, I would try to find the
courage to ask him if we could do certain things. If I wanted to wrestle
downstairs, that was usually code for just playing around a bit and then
seeing what develops.

 Sometimes I didn't tell him I wanted to crossdress for him, and I would
be excited enough to go pretty far.

Most of the time though it was just oral sex. He liked blowing me but it
wasn't all that fun for him because I usually came so quickly. As for
anal sex, he asked, in the middle of summer. He posted the question quite
innocently alluding to it and asked me if my mother ever took my
temperature back there or anybody else for that matter. I said that I had
fingered myself back there but only if I was in the shower using hand
lotion for lube. When I was in the hospital for pneumonia for a week and
a bit, I did get a bunch of enemas and I told him that I really enjoyed
that experience, especially when they took the time to carefully lube and
finger my hole before the stuck the nozzle in to fill me up. I told him
that I was pretty sure that the male nurse that was doing this was doing
it because he enjoyed doing it to boys, especially because after the
second one she started doing them later at night when there was nobody
around. I usually got an erection after that but he never made any kind
of over it sexual move on me and I was usually left to masturbate in my
hospital bed afterward or in the morning if I fell asleep before I got a
chance to.

Anal sex was with him as the receiving and giving partner. He brought in
a few adult magazines, including some gay ones showing anal sex. My
favorite one was this younger looking boy getting introduced to it by
middle-aged guy fingering him while he looks over his shoulder first in
concern and then with surprise and lust on his face, and then he went to
open eyes and mouth surprise when the guy finally stuck his cock in his
ass. The part that looked really sexy was seeing his erection all hairy
and covered with Lube plunging in and out of his hairless asshole. I told
him that looked fun and he offered to be on the receiving end if I had
time and I said that I did. He came well prepared with lots of lube plus
a large towel to clean up with afterward. All in all it didn't take very
long as I was so excited and I find the novelty of being inside
somebody's warm ass just too much for me and I came after I think only a
half dozen strokes into him.

After I pulled out and wiped up the mess, Healy back there asked me if I
was going to finish him off so I took that as being that he wanted me to
suck him off until he came which I did. The first few times he was pretty
timid about forcing me when I was giving him head but this time he would
hold  my head somewhat forcefully making me stroke up and down on him
until he came in which case he held my head down while he blast it into
my mouth and throat.

We did that a few times, and I finally got up the nerve to order some
more sex toys, except this time I ordered them through one of his
magazines and had his home address as where they were going to be
delivered. When he got them he knew he didn't order them so we just
brought them to our next time that we were going to meet and ask me what
was in the package. I told him that he could try them out on me if you
wanted. One was a big white plastic ribbed massager as they used to call
them in the magazine. With a cryptic message on it not to be used on
mysterious calf pain or something. Another one was a rubber dong it was
quite large but also had this tapered up curve to it which I found for
some reason amazingly arousing to look at my masturbated looking at the
picture of it in the magazine as if it was a real dick in my ass.

A bit of it was some more lingerie, this time some sort of filmy stuff
and some more crotchless underwear. The final item was this latex sleeve
that you could put over your vibrator to give it this spiked look like a
French tickler only the little spikes went most of the way down it. You
were supposed to roll it down over a vibrator and use it that way I had
the idea that he or I could wear it like a condom and fuck the other
person with it.

One weekend when I knew he was coming, I dressed up in some of my sexy
stuff underneath my regular clothes when he got there I asked him to
undress me a bit and he asked oh that's nice why did you dress up like
that and I answered him if I'm going to be treated like a slut, I should
at least dress the parts shouldn't i. And that's sort of how I asked him
for anal sex.

That took a bit of work though. He didn't want to make a big mess in me
so he wore a condom, the first few were these yellow colored ones and
later ones where these thick white ones that were almost opaque. To this
day those are still my favorite colors of condom to have somebody wear
for me.


The first time we did this I was on top of him sucking him off and he was
fondling my ass and then slowly fingering me and spreading Lube over my
hole and stretching me out. He used the toy on me but I was still a
little anxious so when he inserted it his cock into me it didn't feel
very good and I told him that he should pull out a bit and use the toy a
bit more. Eventually I felt relaxed enough about it to have him stroke
more than slightly inside. He did finally come sort of grinding is
testicles into my ass crack while he was all the way inside.

We had sex a few more times into the fall. One time, we met at the Annex
Building and then he drove me over to his house for some fun in his bed.
That was a lot more relaxing and then finally the anal sex for that felt
good enough that he managed to make me come by only slightly stroking me
while he was doing it. What I was thinking about when I was coming was
how is cock looked inside the condom with his dark hairs sort of visible
underneath the latex, and all the lube and precum mixed in with it
sliding around inside of it. When he pulled out and laid back, he didn't
take the condom off right away and I had a good look at it and I was
still so horny so I immediately put my mouth over it fresh out of my ass.
The Taste is blue and a bit of something else was really exciting. And I
actually managed to get him hard again. It took a little longer but I
made him come again feeling the condom with even more semen, and then
while holding it at the Beast keep it from licking out, I nipped off the
end and broke it and suck the contents out and swallowed it.

Our best time though came on a ski trip, I wasn't supposed to go but they
needed to pad out the numbers of the seniors by getting a few Juniors
from high school added on to the trip so we could afford to rent a
chalet.

 Because there was some younger students there three of us he got asked
to be an extra chaperone just to give some extra hands. Two of the other
students that were my age that went had older siblings to go with but I
was the oldest one in my family except for a sister and she didn't ski.

The day of the ski trip we were supposed to leave on the first ferry from
our side in Gibson's at 6:20 so he arranged to pick me up at my house at
to 5:30 so we'd have lots of time to drive to the ferry. We didn't have
anybody else with this in his car and I brought along some books and some
school work to occupy me as I was a little behind in that, and that was
my punishment was that I had to do some homework while I was away on this
4-day ski jaunt.

We didn't talk much until the fairy cuz I was a bit tired and still a
little sleepy so I dozed on the drive down there and then a bit more
while we were parked in a lot waiting to get loaded on. Most of the other
students were going to be taking a borrowed School Bus driven by one of
the senior teachers. But they wouldn't leave until a later Ferry at about
8:30 so we would have a lot of time there and we could get dressed to go
skiing and then get loaded up onto these skis while they were still
unloading all their stuff and hoping to get up onto the slopes by maybe
noon.

 When he got out of the car he said he was going upstairs to get some
breakfast and he asked me if I wanted something myself so I went up with
him and we ate what the locals call up there the sunshine breakfast,
scrambled eggs made from liquid egg, some hash browns which are actually
pretty good a big load of Hollandaise and bacon or sausage depending on
what you wanted or what was available

I was pretty hungry as I hadn't had anything yet that day, and he had his
and took his time as he had coffee to go with it. We got back to the car
well before it got in and I wanted to talk to him. He asked me if I was
going to enjoy skiing and I said I probably would but not as much as I
was going to enjoy sucking him off somewhere on the highway on the drive
up there.

He seemed a little taken aback, and I wouldn't open my bag to show him
that I didn't just bring school work but I brought some of these small
porno mags like Penthouse form and human digest. The latter one I really
like because it dealt with kinkier subjects like anal sex gay lesbian sex
water sports enemas latex clothing bondage and discipline. I used to buy
these at the local General store owned by the superintendent of schools
and his teacher son was one of mine. I used to just skim them pretending
to just be casually interested before I moved on to close but I sometimes
would hide the better issues if I wanted to look at them again before
they got moved on for the next month's stuff. But almost immediately that
got noticed and the lady behind the counter put them all in behind where
I put them and just said to go to the counter and ask for them as they
set them aside for me.

Predictably some of my favorite stories are the ones about boys losing
their gay virginity to an older lover. The drive up to the ski resort
Whistler used to take a lot longer back in those days. These days it only
takes about an hour and a bit but back then it took close to two as the
road was pretty treacherous single Lane divided and not very many passing
lanes for faster vehicles.

While we were driving there I turned on the passenger side light and it
started reading the magazine to myself at first. And then gradually I
started reading it aloud. I could tell he was uncomfortable with this not
because we might get caught but it was just sexually frustrating him and
he had to keep both hands on the steering wheel on the freshly plowed
highway.

When we got clear of some of the slower traffic, I told him about a small
little logging area that was coming up where he could make it turn off
the road and take a break. I said the only people that used it were in
the summer we're off rotors and then logging companies. Nowadays there's
a big golf course and a bunch of houses there now but back then it was
very isolated between Horseshoe Bay and squamish.

I hinted to him that if you did pull over, I'd be in the back seat
waiting for him to join me. He didn't talk much so I thought maybe I'd
spooked him but I could see he was still pretty hard in his pants so I
reached over and I was fondling a bit while driving he asked me to be
careful as you didn't want me to make him shoot off in a shorts first. He
found that little pull off to the road quite easily it had been plowed
and salted and graveled as sometimes big rigs would go up there to back
up and turn around to go back along the highway. But this time we had the
place to ourselves. I told him he should go into the back seat and lie
back and I join him so he did I am buckled his pants pulled them apart a
bit and fished his cock out of his underwear so I could suck on him. He
got into it pretty quickly moaning and grunting and I was using one hand
to stroke myself in my pants. It seems to take him forever to come, and I
was worried about that some other vehicle would drive off there and
discover us doing this. I had it at that point heard about couples
getting caught having sex in cars sometimes by the police sometimes by
hikers and sometimes by other vehicles.

He shut off quite forcefully and I tried to catch most of it in my mouth
some of it ended up on him and on my cheek and lips so I cleaned up him
as best as I can and lick my phone face clean and he got a Kleenex out to
clean what was left on my face.

We got ourselves organized back into the front and drove off. It didn't
take all that long about 10-15 minutes. We rejoined traffic. But it
doesn't look like anybody had noticed that we were off doing anything. I
didn't bring any of my sex toys along is that would be very difficult to
explain but if you porno mags yeah that was par for the course back then
for teenage boys. I told him that I hope he brought condoms along just so
we wouldn't make too much of a mess. If we could find any privacy to do
that. I wasn't too hopeful though from what I understood it the Chalet
was too big rooms plus a whole bunch of smaller bedrooms that you'd have
to double up on.

We got there and there was already somebody there, somebody hired by the
owner of the Shelly to clean it up for us before we took possession of it
and it also come by afterward to collect the key from us and clean it up
again. In the course of talking with him we discovered that the original
Chalet was quite a bit smaller just a couple of small two cabins and then
they built this great big one with all the connected bedrooms as the
Shelly got more popular as it was owned by a student union bunch of Simon
fraser. I asked about how big the cabins were and he said they were
pretty nice they had their own hot water tank and a wood stove but they
were removed all the cooking areas out of them as that it all been moved
into the big building years ago. I tried not to let on that that idea
appealed to me I said that wasn't sure cuz I might want to be up late
playing games with my friends as I'd also bought along a few board games
for the evenings

We got our stuff stored into one of two smaller Oak buildings and we had
a talk there. He told me that absolutely nothing would go on during
daylight hours when there was a possibility that someone might come up
from the main building up. I told him I understood perfectly. We put on a
small fire in the big building to warm it up so that when everybody else
arrived they wouldn't have to prep with the cold building that you
couldn't get out of your winter clothes in.

Cuz I understood it also there was going to be shared cooking duties
there was one parent coming along three other teachers and they would
share some of the cooking duty but it was understood that all of the
students would eventually help with one meal in the evening

The other people arrived on the bus and in one other vehicle. That last
one was a surprise because it turns out that they had to bring all the
groceries in that station wagon as there wasn't room in the smaller
School Bus they had planned on using.

Someone had posted a meal list and a bought all the stuff for it. As I
Leaf through the pages of it I could see it was mostly going to be cold
cereal or hot porridge in the mornings but only if you were going to cook
it yourself or scrambled eggs and bacon and stuff like that and maybe
toast. Everybody was expected to pack their own sandwiches they brought a
lot of stuff for that so you can have some variety. Me at the time I like
that weird pimentalo for macaroni loaf that they used to make. As I went
through the list a little further I saw somebody had added a meal that I
knew how to make cabbage rolls. I don't know why that was on there but I
see that from whose handwriting that was it seemed to be one of the other
teachers and then I remembered is that we had an evening dinner at the
school and students in homak including me had to cook something for it
and I chose cabbage rolls and I guess somebody remembered how good they
were.

Getting me up food squared away took most of an hour but not very long to
get people's room assignments assorted. Nobody complained that I was off
in the small side building, most of them wanted to be in the big building
is it was newer it had nice beds and was quite a bit more fun and even
had a television with cable. A novelty back then.

We hadn't really arrived early enough to get a full ski day in so us
Juniors we're going to get three full days of skiing in the others the
seniors I think 8 or 9 of them, they would get a half ski day today, get
two full days and then leave early whereas we'd be around for three full
days after this day.

Predictably the older students were skiing today hurried up to get out of
there so they could get on the lifts by 11:00 or so, the two other
students that were my age weren't supposed to go skiing today, but they
did manage to convince a parent to supervise them on a trip through
Whistler village. Back then there wasn't much to see like there is now.
There was a few restaurants mostly greasy spoons a few bars with burgers,
no fast food joints yet and one small sort of different Grocery and a
couple of ski equipment places.

I was thinking of joining them, I knew both these students quite well and
I knew the parent quite well but I made out like I wasn't feeling well
from the trip and I was a bit car sick from all the turning and jostling
and the big meal on the ferry.


The teaching assistant who drove me said that he had to Mark papers a bit
and he said he would be fine with sticking around until in the afternoon
when everybody came back from the slopes are from wandering around the
village and supervise me here.

With that, by 10:30 the main Chalet was empty of seniors in their
supervisors, and the two others kids my age were just figuring out where
they were going to go. There was also a cross-country ski area and they
kind of wanted to see that to see if they'd like to take up that sport.
So they do a little shopping first and then go to the cross country ski
area and try it out for an hour

I pretended to be disappointed that I had to stick around there, and R.
Ask me if I needed some thing to calm my stomach. I told him my stomach
was fine I was just making an excuse. I told him that I was very happy
that he chose to stay around. I made us some hot chocolate in the kitchen
and I asked me if you wanted to go back to the swallow building we were
going to be staying to have it. And he said that was fine.

When we got there or at least on the path I think, he told me you didn't
have that many papers to mark but it sounded like a good excuse to a
parent and another teacher. At that point in my schooling most of the
teachers knew I was a pretty big handful, being a bit ADHD and maybe even
a bit of a autistic person which would be was very unusual for the late
seventies. All they knew as I was difficult to deal with. I was smart but
I also loved correcting other students and teachers when they got shit
wrong.

I guess they felt glad that they could go about their stuff today and not
worry about anything. About the only thing that we were tasked to do was
sometime around 4:30 or 5:00 is to get the stuff out of the cupboards in
the fridge organized for that first evening meal of cooking. It was going
to be pretty simple though. A whole pile of Kraft macaroni and cheese
some ground beef to go in it, a bunch of garlic bread and some spaghetti
for the students who didn't want to eat Kraft dinner.

I got my books out plus my papers luckily there was a decent size kitchen
table is that we could use either end of it and not crowd the other one.
The papers he marked were nothing too spectacular grade six stuff. My
stuff was a bit more complicated, because in grade 8 computers did just
come out but I've been using the computers in the Annex Building from
nearly 2 years already so I was already pretty talented with that so in
grade 8 I was actually taking the grade 10 Computing science classes. And
then I was also tutoring some of the students who were in various classes
on it as well

I wrote also out I think it was a chemistry paper but I'm not sure
Ferguson yeah chemistry paper. I got it out of the way pretty quickly
just half an hour or so. I was actually getting a little hungry, so I was
going to suggest to him that we go down and get something out of the
cupboards or fridge for a bit of lunch.

While we were making stuff in the kitchen, we were kind of beating around
the bush about talking about what we were going to do later on or at some
point on the trip. It was kind of as if there is somebody in there
listening but the place is completely empty. Front door was locked and
bolted and new back door only let out to the bushy areas behind the main
building to the smaller out buildings one of which we were in.

I told him that I really enjoyed giving him that blowjob in the backseat
of the car on the way there. I asked him if he felt up to doing something
once we had some lunch. He kind of looked at me oddly as I remember, what
do you agreed that it was probably pretty safe to do a bit more stuff
while we're up there.

Once we finished our lunch we took our drinks back to the out cabin and
resume talking. He liked some pornography, and one of the things they
liked was this new thing called videotape. I may have been one of the
first students in the school district to have his own home computer and
programmable calculator back in 1975 and 78 respectively, but he was the
only person in town I do other than maybe a couple of the Richer people
who are big wheels they had a vcr.

I'd heard of a few of these tapes and movies, mostly from adult
magazines, titles like Swedish erotica, Emmanuel, Maryland chambers,
sica. All from the Golden Age of porno movies. He told me about a few of
the other ones that he'd seen predictably though they were gay movies so
I didn't see very many advertisements for these and some magazines didn't
carry gay ads at all.


I talked to him about watching Emmanuel on late night television. He was
astounded to hear it because it was considered softcore pornography, and
therefore not easy for anybody to rent. But they showed the film on a
local television station that was independent of the crtc who regulated
that sort of stuff. At that time of the night on Saturday it was well
known to kids that that's what was playing on there and usually the next
week on Monday and Tuesday the kids would all be off on the school field
out of your shot of adults were in quarters of the hallways talking about
what they'd seen on there. My favorite part of the Emmanuel movie was
when she was talking with some girl and the girl was rubbing her crotch
through her panties. I thought it was much more arousing than actually
being able to see what was going on.

He opened his suitcase and got out from the back inside of a flap some of
his magazines. Predictably I hadn't heard of any of them before. Mandate
was one of them that I still remember now. The others were European quite
often in a foreign language usually german. One that really caught my eye
was an English one about transvestites. He said he ordered it because he
knew that I enjoyed cross-dressing and would like to know a bit about it.
I leave through it and it was a lot of it was guys dressed up his women
and makeup wigs and stuff going about their day doing very ordinary stuff
no real sexual component to it at all like I had that was the first time
that I understood that you could be a cross-dresser but it wasn't
necessarily a sexual thing. Still though I got pretty horny looking at
the pictures. There was one guy dressed in a really nice outfit and then
they showed him getting dressed up into it on for top of some lingerie
and I told him I could just imagine myself in that.

I talked with him about one movie that I saw that didn't make a lot of
sense on that late night television channel. I suspected it was a gay
movie, but it was from Brazil and it didn't show quite a lot they just
sort of alluded to stuff. He said that he remembered seeing it I knew
that had been cut down quite a bit because he'd seen the ads for it in
the magazines he got and that was nearly an hour and a half long and the
cut on this station was only about 45 minutes. There was one part where I
remember this older man and a teenager with your having dinner, and you
can see the boy getting sleepy like he was drugged by what he was
drinking from his glass, and the next thing you see is his feet inside
rolled up carpet being snuck out of the guys house into the trunk of a
car to end up in a dump all tied up getting covered by trash.

I did know by then that men did commit sex crimes. But I had trouble
imagining what that would be like. However, one men's magazine that I
bought how to pictorial in it of a woman going out on a date with a guy
and then you cut to her being pulled out of a pond by police obviously a
drowning victim but her hair is all wet and messy and her pubes as well
and she's still wearing her lingerie except it's all wet a bit muddy and
the kinkiest part of all is your stockings had tatters in them. And I
found the most exciting part for me at least was the photographs of her
or at least photographs of the police taking photographs of her while
they zipper up into a body bag I presumed.

I had bought that magazine, but I didn't leave it at home I'd left it at
the Annex Building inside I didn't want to get caught with that one by my
parents cuz they would probably misunderstand. R. Said that this kind of
activity was probably BDSM and he explained it to me as usually being
consensual, and it could be his team as somebody being tied up and
tickled or it could be as Extreme as someone getting tied up hit with a
belt or something else like that, and then having sex while tied up sort
of against their will, but it was understood that that was going to
happen before they started so it wasn't really rape.

He got out One More Magazine out of his pile and this time it was more
along the lines of that it was crossdressers getting tied up by women and
subjugated. Some of them were forced to give oral sex to the woman. One
man was being fucked up the ass by a dildo. And one other man was forced
to have sex with another man while dressed up by the woman. I found these
ones to be very exciting and real turn on.

I had finished my homework by then and I told him that we had about an
hour and a half before we had to go back down to the other place to get
ready for evening meal. I had the smaller room, he had a larger one and
this one actually had a larger bed in it. I suggested that I would take
some of the clothes that I'd brought along and get changed in his room
and then he could join me when I was done.

Hi God my clothes bag out of my stuff and went into the room, I didn't
close it completely so we could talk while I changed. The top I selected
was a bustier that I liked that I got from a second-hand clothing store
from a catalog along with the garter, and stockings. I thought that I
wanted to add something to it so I put on a pair of these sexy satin
panties.

I had trouble predictably connecting the garters to the stockings. So I
asked him if he was available to come in and help me dress. He took his
time to admire me before he came close enough to help me attach the
Garter to the Hem of the stockings. My mother never wore them, but I had
seen them on one of her sexy neighbors and one of those people's friends,
which I remember very clearly as I was playing under the table once with
some toy cars while they were talking and a couple of them the English
lady and her friend, had these very sexy garters and stockings on going
up under their dress.

Are stepped back when you connected them, and got up onto the bed to lie
back and put my hands behind my head so he could admire me. I was almost
challenging him to actually come over and do something. Predictably
though the bustier was flat so I told him he should get two balloons out
and blow them up so that I had something there.

He quickly inflated the two yellow balloons. And put them in the cups of
the bustier. I could see he was getting hard underneath his pants but I
didn't reach for him I just laid back propped up on the pillows, trying
to relax while he moved the cups up and down to make sure the balloons
were well centered in the cups and then he went and adjusted the straps
so they were at the right height. He said that I looked good enough to
eat, and I said that I'd prefer something else. And I asked him if he had
brought lube and condoms.

He said that he had and he went over to his suitcase to pull him out of a
pocket. Back then there wasn't much choice in lube and or condoms, so the
lube was KY Jelly which I knew about. I had bought it a few times to
finger myself with and to stuff my ass with me hard white plastic
vibrator that I bought me a order. I told him about it and I brought it
to school so he could use it on me and he only had it inside me slowly
pushing it in and out before I ended up coming all over the place. He
like the way that my ass hole glistened with the lube and gaped a little
bit so you started fingering me and I had him roll on a condom so he
could have my asshole. I was a little bit unless excited after my first
orgasm but that quickly came around as we were slowly thrusting and noted
me breathing on my ear and fondling my fake breasts and cock through the
panties and bra. At one point he was gasping and I wanted him to press
himself against my breasts so I got him to pull out and roll me onto my
back so he could fuck me missionaries position. And while he was
thrusting in and out of me I reached around to guide his ass in and out
and I even rub my finger up and down his ass crack and anal opening. I
look down, and I could see it going in and out of me, lube smeared along
it with my own juices from inside, and I could see a bunch of his hair is
trapped underneath the thin white latex. His orgasm was so sudden all he
could do was just gasp and thrust himself all the way in and hold himself
there while he was coming. He held still for seconds and pulled himself
off and I was still pretty horny so when he got on his back to rest, I
got up and got between his legs and started stroking his cock which was
getting a bit soft inside the condom admiring all the semen swirling
around inside it and I wouldn't took the entire thing that had just been
in my ass into my mouth and sucked him off for a while until he was
starting to get stiff again. And then I pulled the condom off spread the
Steam and everywhere and licked it off, and then started sucking him
until he finally held my head down and he came again