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BACK TO LISTINGS
A FIRST ENCOUNTER by Shadow [ True Story ] [ First Time ] [ Anal ] [ Boy / Boy ]
& Viewed 57505 times Voting
I had checked into the motel the night before and I went to the
continental breakfast the next morning. While I was drinking
coffee and eating a blueberry muffin I noticed a man about my
own age getting his coffee also. We started talking while we
finished our breakfast snack and he told me his name was Mark.
When we had finished he said he enjoyed talking with me and
asked if I would be staying at the motel again tonight. I told him
that I would be there a couple more nights. He said maybe we
could have a drink together this evening after work. He gave me
his room number and said to give him a call when I got back.
That evening after I got back and changed into a pair of slacks
and golf shirt I gave his room a call. I told Mark I was back and
asked if he still wanted to get together for a drink. He said
definitely, he did. He said he had a bottle of scotch and a bottle
of bourbon in his room and to come over there and we could
mix some out of his bottles. I said that would be fine and could
I bring some mix and ice. He said he already had all that at his
room, just come on over whenever I wanted to.
I went to his room and knocked on the door. Mark had changed
into his causal clothes also. He had everything laid out on the
counter with a bucket of ice and the glasses ready to make a drink.
He asked me what I would like and I said a scotch with soda water.
He made me a drink and then made one for himself. We sat down
and started talking as we sipped our drinks. He was very nice and
quite interesting to talk to. It wasnít long before our glasses were
empty and we mixed another one.
As we finished our second drink we were both more relaxed and
felt like good friends. He seemed to feel free to talk to me about
anything that had gone on in his life. He didnít pry but would ask
me a few questions about whether I was married or not. I told him
I had been but had just recently been divorced. He asked what was
the worst part of getting divorced. I told him it was the emotional
part that had bothered me most in the beginning. He asked me if
not having a sexual partner available all the time was difficult.
I told him that part was what bothered me most now that I had begun
to get over the emotional hurt. He said that would bother him a lot also.
We made another drink and he asked me if I had had a tough day.
I said it had been about like most of the others but I did get tired today.
He said when he got really tired he put some quarters in the bed
vibrator and that was very relaxing to lay there and feel it. I told
him I had not used mine but would try it sometime. He said he
had some quarters and I could try it now. With that he put a coin
into the timer and it started running. He said to lay down on the
bed and feel it. As I started to lay down on the bed he said I
probably needed to slip off my pants so they wonít get wrinkled.
I unfastened the waste band and the zipper and slipped them
off and hung them over a chair in his room. Then I laid down
on the closest half of the bed. He had begun to take off his
pants also and laid down on the other half of the bed. I had
on white jockey shorts and I noticed he had on a pair of light
beige boxer shorts with three snaps at the waste band. As we
laid there the vibrations felt very relaxing and quite good.
He said again that he certainly understood how much a
divorced person could miss the sexual activity they were
used to. I said that I really did and sometimes it was the only
thing I could think about when it got really bad. He asked if
that happened a lot and I told him unfortunately it did.
As we talked about sex I began to feel myself beginning to get
an erection that started to show in my shorts. I turned a little
toward the side of the bed away from him so it wouldnít be so
obvious if I got a full erection. It would not show as much in
his boxer shorts if he got one as it would in my jockey shorts.
He put another coin in the timer and when he laid back down
he turned a little on his side toward me. I caught a glimpse of
something that looked very long and thick going down his leg
in his shorts. I couldnít tell if he had a partial erection or if that
was just the way it looked when it was soft, but if it was, he must
be huge when he is hard.
When he laid back down and turned toward me he got a little
closer to me. I could feel him brushing against me. He asked
me if this was one of those times that I missed sex a lot.
I answered that it was. He said he completely understood
because he felt the same way.
With that I felt him move a little closer to me and he begin to
slip his knee under my leg closest to him. As he moved closer
it tended to turn me more on my side with my back toward him.
As he continued to get closer to me I began to feel against my
thigh what I thought I saw in his boxer shorts. It didnít feel
completely hard but was long and as big around as a beer bottle.
I couldnít believe how large it felt when he pressed against me.
He was beginning to rub me with his hands and it begin to feel
really good. By now I was almost completely hard. I felt him
slip his fingers into the waste band of my shorts and slowly
begin to pull them lower and lower on me. I tried to just relax
and not move but inside I was so nervous it was hard to just
He continued to pull my shorts down until I felt them begin to
slide over my buns and slide down on my thighs. He said to just
lay still a minute while he got something from his suitcase. It was
laying just across the room and he was back in just a second. As he
was laying back down on the bed I heard the snaps on his shorts
being pulled open. I felt him come back toward me and he hooked his
fingers in the waste band of my shorts and took them the rest of the
way off my legs and dropped them on the floor. Then I heard him
remove the cap to either some hand lotion or something like that
because he began to rub some of it on me.
He rubbed it on my lower back and then on the outside of my buns.
Then he put some more on his hands and begin to rub it between
my cheeks. He was very slow and gentle and didnít really touch
me right on the most sensitive spot. I heard him unscrew the cap
from a jar of vaseline and in a minute he was easing his fingers
between my cheeks again and this time I felt his finger gently
rubbing some right on my anus. It felt so good when his fingers
touched my anus that I would jump a little as his finger brushed
over it. That prompted him to ask if it felt good to me. I told him
it did and I was sorry I had jumped when he touched me, but I
just wasnít used to being touched there. He said he could tell
I had not been touched there before, but to just relax and enjoy it.
He continued to rub it all around my anus and sometimes he
would put a little pressure on it like he was trying to insert his
finger a little. Finally I felt the tip of his well lubricated finger
begin to slide just a little way into me. He didnít push hard and
it felt good just barely inside me. Mark just held his finger very
still for awhile and then begin to rotate it a little making sure to
get the lubricant completely on me. I just laid very still and let
him slowly massage me with his hands and fingers.
I felt him turn away for a minute and heard him pick up the jar
of Vaseline again. This time I sensed he was putting it on his cock.
I was still very nervous as well as excited with what was going on.
I didnít know for sure what he wanted to do but thought he probably
intended to try and put his prick in me. I knew it was so thick that
I would never be able to take it. I felt him move toward me again
and I felt the head of his huge cock begin to brush the outside of
my cheeks. He begin to push the head between my cheeks and to
slowly move it back and forth between them. It was so large it
spread my cheeks wide to just get it between them but it felt so
good to feel it going slowly back and forth in my crack.
Finally he stopped moving it and positioned the head right on
my hole. The head was so wide it covered the complete hole
and a lot of the surrounding area around it. It felt so hot against
my hole I liked the feeling of it being there. He had the largest
prick I had ever seen on a man before. He asked me if it felt
good against me. I said it did but it was so large I would never
be able to take it inside me. Mark said he would never hurt me
and if I want him to stop he will. He was not pushing it into me
but instead just holding a little pressure with it against my hole.
He said to just lay there and try to relax and he will go very
slow and will stop anytime I ask him to.
We laid still for a few minutes and he would rub me with his
hands and sometimes pull me back toward him as he rubbed me.
When he would pull me back toward him I would feel the
pressure on the head of his cock increase against me. I could
feel the head slowly trying to open me enough to get the tip inside.
It felt very erotic to me and had not hurt at all, but of course it
had not gone in me either. He tightened his grip around me and
pulled me back toward him again. This time I felt that huge
mushroom head start to go in a little. As soon as he felt it start
to open me a little he stopped pushing and held very still for
awhile. He seemed to know exactly what he was doing and
exactly how to do it.
Soon I felt a little pressure against me again. He was gently
trying to force a little more of the head into me. I knew I had
two very strong sphincter muscles in the anal opening and
doubted they would ever open enough to take something as
thick as his prick. He said he was going to stop for a moment
and put some more vaseline on us both. I felt his finger on
my hole again and he pushed it inside with a lot of lubricant on it.
He put a lot on the inside of my hole and put some more on his
swollen prick. He again pressed up against me and positioned
his cock against my hole.
This time it seemed to start in a little easier. My hole was being
opened more and more by that giant head that capped his long,
thick, rock hard shaft. I began to feel it stretch the first sphincter
muscle in my ass hole until I thought it would tear my anus.
It felt like a hot poker was being forced up my ass when finally
I felt the head slip into me between the first and second
sphincter muscles of my ass hole. I jumped as it lodged in me
and he immediately stopped the pressure and said just relax
and donít move.
He said in a little while I would get used to having it in me a
little ways. I told him it was so big I knew I could not take it
completely in me. He asked me to just lay still and we would
see if I can take any more of it. He said he would go very
slowly and would be very gentle. He also promised me again
he would take it out if I asked him too We just laid there for
at least four or five minutes and my anus begin to relax and
not hurt so much with the head in me.
I really wanted to feel him completely in me but just didnít
believe I could ever take all of his overly thick cock. The girth
of his cock continued to expand as it reached the middle of it.
I knew that every inch of it he put into me would stretch my
hole wider and wider. To take it all would be next to impossible
for me. Finally he asked me how it was feeling now. I told him
I had relaxed a little and it felt better. He said he was going to
hold a little pressure again and for me to try and push back on it
and see if I could take a little more in me.
He reached around and took my now completely hard cock in
his hand. He slowly began to move his hand back and forth on
my cock. It felt so good as he slowly jacked my cock back and
forth. As he brought his hand down on my cock he would pull
me back toward him and I felt him begin to apply some pressure
against me again. I tried to push back a little on his prick and
started to feel the head begin to push against the second
sphincter muscle. This one was stronger and tighter then the
first one. With the head in me I could feel the rim of his cock
trying to completely enter my ass. To accomplish this the
second sphincter would have to open enough to get most of the
head past it.
I tried to push back harder and the pain from being stretched
so wide almost made me quit. I held my breath and pushed
back even harder and felt the head start to slip slowly into me.
He knew immediately that the complete head of his cock was
finally impaled in my ass hole. He held me very tight with his
hands and said not to move until I get used to having it in me.
My anus was trying to contract but his thick prick kept it firmly
stretched open. It felt like if I could just close my hole for just
a moment it would feel so much better. I almost asked him to
take it out for a minute and then we could try it again.
He continued to slowly jack me off and it felt really good.
It took my mind off how stretched my ass hole felt and how
much it hurt. In a little while I felt the pressure against me
start to increase again. I knew he was trying to push his cock
a little further into me and I really wanted to take it. I felt it
go in a little further and then I felt him pull it back about an
inch and immediately push it back in a little further then it
was originally. He was slowly moving it back and forth and
each time going a little deeper in me. Since he was still
working the first part of his cock into me it was continuing
to stretch my ass wider and wider.
I thought if I can just get it in past the middle of his prick it
wonít get any thicker as he puts the rest of it in. I thought my
hole would split it was stretched so tightly around his huge prick.
He said again how tight my ass was and how good it felt as it
clamped so hard on his cock. He said it was the tightest and
felt the best of any he had ever fucked. I knew if I could ever take
it all and get used to it I would never forget the sensations I would
feel to have him fuck me.
I wanted his cock completely in me. The fact that it was so large
and thick were both a deterrent and an erotic turn on. It hurt to
have one this large inserted into your anus, but taking a cock that
size was definitely very erotic to me. I think I now know what it must
feel like when a woman gets fucked with a large cock. I have often
wondered what it must feel like for her and now I know what she feels.
Mark knew exactly what I was feeling as he continued to push
inch by inch deeper and deeper into me. He knew when to stop for awhile
and when to push it in a little deeper. As he slid in deeper I finally
felt my ass not being stretched any wider. I knew he must have it at
least half way in me and if it wasnít going to get any thicker, I thought
I could take all of him. He continued to slowly move it deeper with
every thrust. I could feel the head of his cock opening my colon as
it went deeper into me. It felt really good to have that huge prick
in me. It felt like he was completely filling my ass with a hard hot pole.
It didnít hurt to feel the colon being stretched open but my ass hole was being stretched so much it would rip me if it was any thicker.
Finally I begin to feel his balls brushing against the cheeks of
my ass. This was a sure sign that his cock was almost completely
in me now. I was relieved to know there was not much left to go in.
He stopped for a moment and then said to roll over on my
stomach and he would roll over on top of me. As I rolled onto
my stomach he told me to spread my legs so he could put his
legs between them. His prick was still firmly in place deep in
my ass and now I felt him put his weight down on the cheeks
of my ass.
His weight felt good on my cheeks. I liked to feel him pressing
down on them. He slowly started to lift his weight up and pull
his prick out of me a few inches and then slowly push in back in.
He was well lubricated but when he would pull back it felt like my
ass was being pulled inside out. It was so tight around his huge prick
it tended to cling to it rather then his prick sliding out. He continued to
slowly push it in inch by inch. He started to increase the length of his strokes until he would pull his cock half way out and then slide it in again. As the middle of his cock would come to the entrance of my
ass hole it would hurt more since the middle was the thickest
part it would stretch my ass hole completely open until I couldnít
open any larger. My ass was beginning to get used to having his
cock in me except for this thickest part.
He asked me if I was all right and I told him I was but it still hurt
quite a bit and felt like it might tear my ass hole so please be gentle. He said he would but he was ready to start fucking me slowly now. He again assured me that if I felt like I couldnít take it he would stop. He started to fuck my ass with a slow in and out rhythm. He kept increasing the lengths of his strokes until just the head of his cock was in me and then would slowly push the full length back deep
into my ass. I felt like a huge hot poll was going in me but it also
felt good to feel it go so deep into my ass. The size of it was very
erotic and I started pushing back to meet his strokes as it slid in.
As he pulled his cock out on the back strokes I could feel the
rim of the head massaging my prostrate. Then I would feel him
thrusting back into me and opening my colon with the large
diameter of his prick. It felt so erotic to feel his prick going
so deeply into me.
I was so hot I was afraid I would cum while he was fucking
my ass. I would clamp down as he thrust into me and he said
how good it felt on his cock when I did that. He continued to
fuck my ass and begin to push into me harder and faster.
He stopped for a second and spread my cheeks with his hands and said
he was going to get every last inch of his prick into me. I could
feel the base of his cock absolutely at the entrance of my ass.
His long hard shaft was almost driving the head of his cock to the
front of my stomach. He was going past where the colon makes a
turn and his cock didnít turn but just tended to straightened it out.
He really begin to fuck me in earnest. He would pull it almost
out and drive it deep back into me with his full weight behind it.
I could feel the shaft of his cock begin to get even harder and thicker
as he positioned it back and forth in my tight ass hole. His breathing
began to increase and I could sense he was getting close to a climax.
His huge hot prick was driving deep into my ass and I could feel it
getting even thicker and harder as he rammed into my very tight hole.
He pulled two pillows from the head of the bed and said to put
them under my stomach. When they were in place it raised my
ass up until I was about half in a kneeling position. In this position
it would tend to spread the cheeks of my ass a little and give him
even deeper access to my thoroughly stretched ass hole.
He continued to pound his ever expanding cock deep into me.
He told me he was getting very near a climax and asked if it
would be all right to shoot off in me. I told him that would be
fine to cum as deep in me as he could. He began to pump into
me with faster and faster strokes. I felt his cock expand and
get rock hard. He was about to rip my ass hole as his cock got
even thicker then before. Finally he thrust into me with all his
weight and I felt his cock start to spasm again and again as he
shot his hot full load into me. With each shot of cum his prick
increased in circumference with the urethra expanding at the
bottom part of his huge shaft. I just couldnít take anything that
large in my ass hole and I could feel it start to tear as his cock
continued to pulsate in me. His prick throbbed again and again
as the last few drops of cum came out the huge hot head of his shaft.
He left his cock buried in me and just laid down on my back.
I told him when he came that I thought maybe my anus had
torn some. I also told him that he had shot so much cum in
me that it felt like he had given me a cum enema. He told me
he had shot a much larger load into me then usual. He said it
had happened because I was so tight that it felt so good to him
he had come more then usual. He said to just lay still for a little
while and he would take it out. I told him he could leave it in
me as long as he wanted to since it felt better in me now that
his cock was beginning to get soft. My ass was able to close a
little around his prick and it felt so good to not be forced that
far open. He finally slowly withdrew his cock from my ass hole.
He spread my cheeks with his fingers and said there was just a
little blood on me. With that he took some more Vaseline and
rubbed it on the little tear in my hole.
After a little while I got dressed and we had one more drink.
He told me how much he had enjoyed fucking me and asked
if maybe we could try it again tomorrow evening. He said it
had felt better and tighter then any ass he had ever fucked. I
told him I had enjoyed it also after we could finally get it in.
I said maybe we could try it again tomorrow if my ass was
not to sore. He said to get in a tub of hot water and it would
feel much better very quickly. I told him I would and I would
let him know if we could try it again tomorrow and that I really
hoped that I would be able to take it again.