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Story Info

Posting Date 2010-11-22 13:12:31
Author Dirtydan
Title My real first time
Category had a gay/lesbian/bi-sexual experience
Where it happend His Home
Age then 19
Age now 30
Gender MALE
Viewed 326
Story Length 2998

(8 votes / 73 points)

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My real first time


I've only had sex with 1 man in my life, and that was 11 years ago when I was
19. He was a 48 year old married man with two grown children. He was about 5'9"
190 1bs with balding hair and a black beard with some grey. Although he
appeared to be a little on the chubby side, he actually had a solid thick body.
I had just finished my first year of college, and since it was now summer, I
rode my bike whenever I could around town. I lived in Stony Brook and was
attending Spaulding University, so I often rode my bike to the campus. During
the summer, the campus was very quite and deserted most of the time. Even
though I rode my bike to campus, I would usually walk with the bike on the
campus walkways. One time, while walking with the bike on campus, I noticed a
man sitting on a bench. He was apparently having lunch while reading some
papers. As I neared him, he looked up and said hello. I nodded and said hello.
He then said "nice summer day today" Yeah I said, I really like riding my bike
in this warm weather. We then engaged in the usual small talk. He said that he
also liked to bike ride, but hadn't in a while. He asked if I was a student
etc. He told me that he owned his own bussiness, and liked teaching a bussiness
class in the summer. We talked for about 10 min, when I told him that I had to
get going. We shook hands and I left. A few days later I again rode my bike
and again saw him sitting on the bench. We again greeted and had a brief
conversation. This time, He told me that he was really interested in taking up
bike riding again. Thus we talked about biking and exerscise for a while. He
then mentioned how hot the weather was, and asked if I wanted to talk in his
office. He really seemed like a nice guy, so I said "sure ok" However, as we
walked to his office, I began to feel a little self conscience about the
situation. Here I was a 19 yr old guy wearing very short biker pants, walking
to an office of an older man I hardly knew. It was a large office with 2
desks. However since it was summer, he was the only one using the office. There
was a small black coutch next to the window. We both sat down on the coutch and
contiunued talking, he also asked me about my major, how I liked college etc.
My uneasyness was maginified when he began telling me how biking was doing me
good, and that I looked in very good shape. He even told me how he especially
liked my long legs. Now, I felt that he was definately being more friendly than
normal. Just being polite I thanked him, but told him that I had to go
somewhere. As I was leaving, he asked if I was willing to perhaps ride with
him. However, since I now felt uncomfortable about this, I told him that I was
going to look for a summer job, and would be busy. Then he quickly told me that
he had a built in pool, and that I was welcome to come over for a swim. Again I
politely declined his offer. He said he understood, then gave me his home
number in case I changed my mind. As I left his ofice, I now knew for sure that
he was interested in me sexually. I soon realized however that I was aroused by
this. That night, I actually fantasized about him while masturbating. I
fantasized about what he wanted to do with me, I found myself aroused by his
obvious sexual interst in me. I tried to fight these feelings, but after about
4 or 5 days, I decided to see him again.

I called his home early in the morning. He sounded surprised to hear my voice
but was glad I called. I told him I was accepting his offer about going for a
We agreed to meet after he finished teaching his class around 11:30 am, and he
gave me directions to his house. I had decided to give him every opportunity to
flirt with me. This time I was going to be more receptive to any advances he
might make.
As it turned out however, he was more aggressive than I thought. After ringing
the door bell, he opened the door. I immediately noticed that he was wearing a
very short bath robe, which just covered his crotch. It actually apeared as if
he was perhaps naked under his robe, it bearly reached pass his ass. This
definately had an effect on me, and my cock got hard looiking at him. He then
showed me around, and brought me out to the pool. He then invited me back in,
and asked me If I wanted something to drink. We then sat down in the living
room and began talking. He sat down on the coutch first, and told me to sit
down. There was a sofa chair right next to where he was sitting, but I wanted
to make some kind of move. Instead of sitting on the chair, I sat right next to
him on the coutch. I sat down so close to him that our knees were actually
touching. After a few min coversation, I asked him about the comments he had
made about my legs. "you really like my legs" "yes he relpied. I then told him
that I was unhappy about them because they were too thin. "No he said, they
look very good. He then put his hand on my knee and actually rubbed his hand up
towards my upper thigh. "do you mind me touching you like that" No, I relpied,
I don't mind at all. I then reached over and placed my hand on his thigh and
told him I prefered to have thicker legs and thighs like his. I then reached up
and touched his beard and said, "I really like your beard too". When i did
this, he asked me If I was attracted to men. I told him that I hadn't thought
about it before I met him, and that I had never had sex yet with a male or
female. He said he found that hard to believe, but asked if I wanted to have
sex with him. I then showed him my hard on which was clearly visible thru my
shorts. He then rubbed his hand against it, and said "you clearly are aroused"
Yes I replied, you? He said that he was definately attracted to me and that he
really liked younger guys. He then stood up and extended his hand and said,
"c'mon, lets go up stairs." Hand in hand, I followed him upstairs. My legs were
weak and shaky as we climed the stairs, and my heart was racing as we neared
his room. I remember actually feeling an electric shock run thru my body when
he closed the door behind us. It was then that I fully realized that I was
going to have sex with a man. We faced eachother at the foot of the bed, and he
then removed his robe. He was wearing extremely short jockey shorts, and I
could clearly see his load. I could see the outline of his cock and balls. I
immediately reached out and with clearly shaking hands palmed his crotch. He
seemed to have very heavy balls. He told me to take off my clothes, and when I
removed my shorts, my cock was completely erect. He put both hands on my ass
and brought me towards him. My cock was now up against his stomach. I then pu
my hands on to his back, and we hugged. He could feel my heart pounding "Wow,
you're very exited aren't you?" "yes I said, very" "Just relax, he replied" "I
can't relax" I replied, I'm just too aroused." Then he told me to take some
deep breaths and relax. He then asked if I wanted to explore his body first.
"Yes, please" I relied . He said ok, and he then walked over towards the head
of the bed. He proped up the pillows, then removed his shorts and layed down
onto the bed. After he made himself comfortable, he told me to come over. His
cock was not quite fully erect, but as I climbed on to the bed next to him, his
cock became fully erect. He then told me to explore his body. Since this is
your first time, "You can do whatever you want, touch me anywhere, just do
whatever comes natually." He wanted me to get familiar with his body, so I did
just as he asked. I touched and rubbed his hairly legs, ran my nails along his
thighs and stomach. I ran my tongue along his stomach and chest. I kissed his
stomach and chest, licked and kissed his nipples. I touched his beard, felt his
chest hairs. Even thought I hadn't even touched his cock, I noticed that it was
fully erect as I explored the rest of him. Finally I began examining his cock
and balls. I smelled and licked his balls, ran my tongue from his balls down to
his ass. I also squeezed, pulled and stroked his cock. I ran my tongue up and
down the underside if his cock and sucked on his balls, before finally sucking
his cock. I still get aroused remembering how he let me do all these things to
him. He just layed back and let me examine his entire body. He was enjoying
having a much younger guy touching and pleasuring him in his own bed like that.
He kept telling me to do whatever I wanted.
After sucking and playing with his thick cock for a while, I felt the urge to
climb on top of him. Without saying a word, I got on top of him. We were now
face to face and chest to chest. He placed both hands on my lower back and help
me position myself on top of him. My top side of my cock was now laying against
his upper thigh, while the underside was against my own upper thigh. I began to
rub myself against him. As I moved my body, he slightly moved his legs
together, the friction this caused felt very good. In this position, we were
able to kiss and talk to one another. I rubbed my face against his beard, and
he kissed my neck and face.
It felt so good on top of him, his hands felt great oas he moved his hands
around my ass and back. I also lay completely down on top of him resting my
head on the pillow just ablove his right shoulder. In fact, I was so aroused
that I began to loose controll. He could sense this, and he repeatedly told me
things like "slow down" "Easy, calm down". Finally he actually physically
stoped me, then again told me to relax and go slower. I tried to stop, but I
couldn't hold back. I was too aroused. My mind was racing, here I was having
sex with an older man in his own bed. I even loved how my toes felt against his
feet. I was only on top of him like this for about 3 min, when I achieved
orgasm. After he stopped me, I quickly resumed moving against him and very
shorty afterwards felt my cock begin to spasm. My orgasm happened very quickly
and I couldn't controll it. I remember stiffening up and lifting myself up
slightly and looking straight down at his face underneath me.
As I came all over his leg, I remmember saying "I'm sorry". "don't worry about
it" he said, "its ok." Breathless against him I told him that I couldn't help
cumming so quickly, I was just too excited. He again said that he understood. I
then climed off him and began masturbating him. It took about 5 min, before he
came from my hand job. It was here that I first witnessed something about him,
he always shot a big load when he ejaculated and he would usually shootout a
good 5 inches. I used to love making him cum just to see this.

Afterwards we cleaned off in his bathroom and went for a swim. He then told me
that his wife would be home soon and we would have to see eachother again
later. We agreed to meet again the next day. This time we went right to his
bedroom. We hugged and kissed, then he layed down and I began examining his
again. After sucking his cock for a while, I again climed on top of him. This
time I lasted a lot longer. We again kissed and talked as I rubbed myself
against him. Again his hands roamed all over my back and ass. This time
however, he started rubbing the underside of my cock with his middle finger in
a circlular direction. This took me by surprise and I stopped rubbing against
him. I couldn't believe how good this felt. My cock was throbbing while he did
this. I just layed there motionless as he masturbated me like that. "thats it,
just relax and enjoy the sensations" he said. He noticed that I would sometimes
hold my breath while he rubbed me, so he told me to keep breathing and to take
deeper breaths. He seemed to sense whenever I was getting too aroused and would
ease off and rub another part of my cock, we would then exchange some kisses. I
was moaning and groaning the whole time. Finally after about 10 min of this, I
began having trouble controlling my responses. up till now, I had experienced
about 10-12 minor orgasms, but was able to control them by taking deep breaths
like he said. The invetable occured however and I achieved orgasm. When I came,
he just said "Mmm, thats it, enjoy it" And that I certainly did, it was the
most intense orgasm I had ever experienced. I then kissed him for several min,
thanking him for the experience. I then responded by sucking him off again.

This went on for about 2 weeks, with me riding him and then sucking him off. He
then began to ask if I wanted to try anal sex. I reminded him that I was very
inexperienced at this. He assured me that it would be ok, and that he would be
very gentle. This time after cumming on top of him, he said he wanted to enter
me. He took some vaseline and put it on his cock, and we both rubbed it all
over his cock.
He then positined me on my hands and knees. He then entered me with his finger.
He fingered me for about 2 min before asking me if I was ready. He gently
grasped my hips and began rubbing his cock against my ass. I could feel the
head of his cock against my anus. He slowly began pushing it in. It didn't go
in the first time, and it took him several more tries to make any progress.
Finnally he got a little further in, but still not quite all the way. He was
being very gentle, and he continually asked if I was ok. Slowly but surely he
proceeded, when suddenly his cock slid all the way in. We were both taken by
surprise at the suddeness of it, and he gave a deep moan as it slid in. He then
fucked me with a gentle, steady pace for quite a while. There was a mirrored
closet in the room and I could see him fucking me. I noticed that his eyes were
closed most of the time as he fucked me. I enjoyed watching some of the faces
he made, and watching him squeeze and spread my cheeks. Sudenly he began to
loose controll himself and began fucking me really fast, then his entire body
stiffened and he let out a loud moan, then layed down flat against my back. I
could feel his warm cum as it shot into me.

Our relationship lasted for the rest of the summer. When the summer ended I
went back to school, the next summer I got a full-time summer position and
didn't get a chance to see him that summer. Eventually we lost contact.

I never fucked him, and he only sucked my cock once or twice. He fucked me
several more times over the next two months in many different positions. We
managed to sleep together only a few times, whenever his wife was away for
a few days. Even thought I let him fuck me and I sucked his cock many
times, I didn't feel that he was taking advantage of me. I really enjoyed
laying on top of him and being masturbated to orgasm. I also liked sucking
his cock and watching him ejaculate.

I did meet him once a few months back. He is now 60 years old. He had a heart
attack a few years ago and now has to walk with a cane. It was hard to believe
that this was the same man I had sex with that summer. He even apologized to me
about his actions-after all he said, I was a student and he was a teacher etc.
I told him that I didn't have any ill feelings towards him and that I still
fantasize about him and our experiences together.


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