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Category: first time gay sex,

At last – a Straight Man’s First Gay Sex Experience

21 February, 2019 (03:02) | first time gay sex, | By: Gaysexstories

by Tookie (no address provided)

***

A married guy with a curious gay side, finally gets
his dream. (MM, 1st-gay-expr, anal)

***

I’d been trying anal sex using various objects on
myself for some time, it was a little fantasy of mine
to have a real cock but never got up the nerve to find
one until…

My son in law is a huge well-built guy, he is so
obviously heterosexual that he may as well have a sign
saying “gays back off, or else.”

One every other weekend my wife and two daughters went
out on the town leaving me usually at home alone and
my son in law out with his mates, I used these nights
to fill my anus with different cock sized objects, one
particular night I added a twist to the self-abuse, I
put on some of my wife’s undies, a tight skirt and
sheer blouse, my cock was rock hard as I pranced
around the house looking at myself, I imagined I was
meeting a guy who loved fucking married men like me.

I had fucked my arse with a few different sized
deodorant cans and a variety of bottles and a long
slightly … Read the rest

A Con Goer Gets Conned..

20 January, 2019 (17:09) | first time gay sex, | By: Gaysexstories

By Bottomsup (bottomsup@fastmail.us)

***

Anime conventions can sometimes have a real twist. (MM,
1st-gay-expr, anal)

***

I’ve been into Japanese Animation for years, starting
back in college when I was a member of the campus anime
club. I’ve always been fascinated by such incredible
art, and the different perspective on things that the
Japanese use. So I should have been ready for something
strange when I went to this last convention.

I’d booked a room at the con this time instead of
offsite. Offsite is nice for being discrete, but when
the music’s pumping at 2 AM, and the drinks have been
flowing all night, it really sucks to have to get a cab
to your hotel. The parties tend to get loud and sloppy,
since most of the people there are college age or
below. I’m a little older than most, but since I’ve
been an otaku for so long, everyone accepts me into
even the youngest gatherings.

So, it’s 3 AM. The dance is starting to wind down, and
I’m outside having a smoke. The wind is nasty, and it
really sucks having to head outdoors in winter for a
quick hit of nicotine, but what are you … Read the rest

Black Isn’t So Bad After All – an Interracial Bisexual Story

20 December, 2016 (14:44) | first time gay sex,, interracial, Uncategorized | By: Gaysexstories

by Comixs (comixs@hotmail.com)

***

A white couple learns to deal with their feelings 
toward black people, despite their upbringing. They 
seek professional help and things really get started 
with the husband's first visit. (MM, intr, 1st-bi-expr, 
mc)

***

John and DeeDee were the average couple of their times. 
Both had been raised in a white Christian environment 
and throughout their lives were taught that black 
people were not as good as they were. 

Times change though, whether you want them to or not. 

Both are now in their early 60's, having been married 
almost 45 years, and as they grew older the 
neighborhood around them changed as well. More and more 
black families were moving in and more and more white 
families were moving further out of the city, into the 
suburbs. It was only a matter of time before a black 
family bought the vacant house to the side of theirs, 
or perhaps the once slightly down, and across, the 
street from them. 

In order to get a better grip on their lives, as well 
as the way they had been brought up, they sought out 
professional advise, in the form of a psychologist, who 
had been recommended by 
Read the rest

The Basketball Boys

20 December, 2016 (14:41) | first time gay sex,, hot gay sex, Uncategorized | By: Gaysexstories

by Dirty Jim (no address provided)

***

A married counselor at a basketball camp gets in over 
his head. (MM+/M, 1st-gay-expr, reluc, mast, oral, anal, 
orgy, gb)

***

I had been a camp counselor at the regional basketball 
camp for several years. I always looked forward to the 
camps, held at a private college about 30 minutes from 
my home, during the hot days of July. It was a week away 
from my family and other responsibilities. Though I 
dearly love my beautiful wife and my two young children, 
at times I also found pleasure in doing my own thing and 
having time to myself, not to mention the chance to pick 
up some extra cash. 

The work was easy, just keeping large groups of boys 
aged 6-17 focused on improving their basketball skills 
and refereeing the games at the end of the day. I was 
the oldest of all the counselors, having turned 42 the 
month before. There were a number of other counselors, 
but they were all in their early 20's or having just 
graduated from high school. Most of them were stars on 
their school basketball teams and some had played in 
college.

While I had a 
Read the rest

My Bad Boys – an Bisexual MMF Sexstory

20 December, 2016 (14:33) | first time gay sex,, hot gay sex, Uncategorized | By: Gaysexstories

I didn't think it was possible, but Mark had been a
very naughty boy. Again.  It wasn't enough that I had
punished him once...or twice...it just seemed that he
could never get enough of it.  Maybe he was just lonely
and thought that any attention he could get would be
worth it.  So I would be more than happy to oblige him.

   I heard the knock on my apartment door at exactly the
moment I told him to arrive.  When I didn't answer, I
knew he would use his key and let himself in, thinking
he would be surprising me.  Little did he know!

   He opened the door and walked inside...to find me
topless, on the floor in front of the sofa with my
friend Tony's head buried between my breasts.  I smiled
up at Mark and he froze.  For a minute I didn't know
what to do, he just stared, as if he couldn't believe
his eyes.  

   Tony glanced up, smiled, and went back to licking
my nipples, nuzzling them and sucking on them.  He
was incredibly handsome, but not as handsome as my Mark.

   Tony looked like an Italian statue, black hair, dark
eyes, olive skin, a perfect 
Read the rest

A Hot Night in Peru

28 November, 2016 (16:07) | first time gay sex,, Uncategorized | By: Gaysexstories

by Anubis31 (address withheld)

***

He gets caught by the Peruvian Army. (MM, reluc, 1st-
gay-expr)

***

Many years ago I worked for a British bank in Lima,
Peru. I had an American girlfriend, Susan, who worked
for a US airline. We were invited to a wedding in a
small village, just outside the city. We drove there in
Susie’s beaten up old Buick and found the village
without any problems. The party was great, the people
were very friendly, and we had a great time, although
we had a bit to drink and had been smoking pot. We took
our leave of our hosts and started driving back into
Lima, unfortunately getting hopelessly lost. We ended
up on the perimeter road of a military airfield and
were just turning the car around when an army jeep
suddenly appeared.

A young captain, a sergeant, and two soldiers got out,
covering us with a variety of weapons. The officer
informed us that as we were in a restricted area, were
breaking the curfew, and foreigners to boot. He would
have to hand us over to the Internal Security Police.
This terrified us both, as people who fell into their
hands sometimes … Read the rest

A Fantasy Lived

28 November, 2016 (16:06) | first time gay sex,, Uncategorized | By: Gaysexstories

By UncleJoe85 (unclejoe85@hotmail.com)

***

Unhappy at home, an older man seeks to fulfill his secret
fantasy to be loved by another man.

***

A Fantasy Lived, A straight man’s coming out (MM, oral,
anal, romance)

***

After 12 years of marriage, my wife and I have slowly
drifted apart. It was nobody’s fault really. We all
change with time and that which unites two people, does
change. True, the twelve years difference between our
ages did not help, but for me, something has always been
missing.

I always considered myself to be a normal, healthy,
heterosexual kind of guy. Never experienced what some say
was typical childhood boy-2-boy experimentation. I always
averted my eyes when sharing a shower in high school or
in the military. However, I did sneak a peak once or
twice when I knew no one would notice. The problem is
that when I did see something I was ‘not supposed’ to
see, it was difficult for me not to become aroused and
zipping up was difficult.

It’s always been my secret desire and fantasy to explore
that which society then considered improper. With the
introduction of the Internet, the posting of gay stories
and pictures, my … Read the rest

A Day to Forget – a First Time Gay Experience

28 November, 2016 (16:04) | first time gay sex,, Uncategorized | By: Gaysexstories

by Dave (ufpe@hotmail.com)

***

A Bad Day brings about an unforgettable experience

***

It was a rainy and cold night when I entered the smoke-
filled bar just off the Interstate. A series of personal
defeats had sent me home for the comfort of my most
recent lover. My unexpected early arrival found her in
the arms of another and after a flurry of ill
contemplated accusations, we were soon on our separate
ways.

Fearing further confrontations, I eased my wheels into
the unimposing parking lot and with a dash of cologne
entered the dimly-lit room awash in the mid summers rain.
My full intention was to drown my sorrows in solitude and
seek solstice in the motel next door for the night.

The entire day had been most uniquely revealing, and now,
sitting peaceably at the colorful bar, I began to recount
the day’s defeats with a more speculative eye. My second
glass was all but empty when she approached from out of
nowhere. Her husky voice and bedroom eyes were a
tranquilizer unto themselves, and I found myself
expounding unceremoniously on her feigned interest.

She was firm but gentle, goading me to reveal my
innermost desires while remaining … Read the rest

121st Street – A Group Gangbang Sex Story

28 November, 2016 (16:00) | first time gay sex,, hot gay sex, Uncategorized | By: Gaysexstories

By Turbo (address withheld)

***

A guy is in the wrong place at the wrong moment in
time, or is he? (M+/M, nc, rp, intr)

***

Hi, my names Clint Holbrook, and I have to admit that
things just aren’t turning out right for me this week.
Stuck in New York for a convention that my boss has
made me attend (against my will, no less) I’m surely
not a happy camper.

To add to the negative attitude of just having to be
here, getting here just had to be the pits. Here I am
on 121st street, lost and being followed by 3 Hispanic
guys. I can feel the tension and fear rising. How am I
going to get out of this mess?

Let me start from the top. John (my boss), suggested
that to improve our sagging sales, someone should
travel to New York and attend their fashion convention
and bring back a new line of clothes. I got elected. No
volunteering just elected (negative aspect number one).

My plane was scheduled to leave in an hour (luckily I
keep a packed suitcase for these unexpected occasions)
and I had to get to Hartsfield Airport from Alpharetta.
That … Read the rest

Out Personals Online Gay Dating Site Experience

24 September, 2016 (15:12) | first time gay sex,, hot gay sex, Uncategorized | By: Gaysexstories

For many years I had a girlfriend. During our many times having sex together, we often wanted to experiment. I wanted to see her with another girl and she wanted me with another guy or have a group orgy. Frankly, it’s hard to ask friends “Do you want to experiment in a threeway. So, we hit up several online dating sites. We went to straight and gay sites in our quest. I must admit I was very curious as I looked at the other guys on the sites. Nothing came out of our quest except one group sex hookup that was as confusing as it could be. I knew we were a couple at least at the time. But she seemed more satisfied with other guy. Her pussy squirted for the first time.
Not long after this we broke up. She found some way to connect with this guy and steal him from his girlfriend at the time and get married. When I saw her she was expecting her second child.
I managed to date and fuck girls occasionally but hadn’t really filled my bisexual curiosity. After the group sex thing I had a girlfriend for a couple of months … Read the rest

Drinking Beer and Fishing – A First Time Gay Sex Story

20 September, 2016 (03:43) | first time gay sex,, Uncategorized | By: Gaysexstories

by James T. (savannahkid@excite.com)

***

I was drunk as I tried to make myself understood to my
buddies. We were cutting high school had slipped away
for a day of fishing. At sixteen I was feeling “NO
PAIN” after a day in the sun while drinking beer. I was
sitting in the fishing lodge watching the room spin. I
would laugh at almost anything because I was pretty
drunk but Chris and Billy tolerated my childlike
actions.

I don’t know how the conversation and joking had turned
to “the” topic. With three teenage boys everything
leads to sex. I was listening to Billy tell Chris about
Becky a younger girl from the neighborhood. “She told
me she had sucked off two guys at school. I tried to
get her to give me head but she said I was too old.
Shit was I mad at that, to think the guys younger than
me were using her hot mouth. Why not me?”

Being really drunk I laughed and said, “She probably
didn’t want to suck on a small dick.”

Billy looked over at me and said, “Fuck you, I have a
bigger cock than you do, you fucking fag.”

I giggled … Read the rest

Drunken Frat Boy

20 September, 2016 (03:39) | first time gay sex,, hot gay sex, Uncategorized | By: Gaysexstories

By Warwick (jlittle@yada-yada.com)

***

I’m a graduate student and am as gay as a three-dollar
bill. I live in a town, which has one of those 24-hr
adult bookstores, with video viewing booths in the back.
The owners are very cool about not harassing patrons who
go into booths together to suck each other off.

I was cruising around the back room late one Friday night
when this gorgeous young studly guy came staggering in,
obviously quite drunk; just drunk enough, I thought, to
allow himself some sexual experimentation maybe.

He went into a booth, and I could see under the door that
he was lowering his trousers. I tried the door to see if
he had locked it, and he had not. Getting no objection
from him, I entered the booth. He was still wearing his
white cotton boxers (a huge turn-on for me), and I could
tell that his cock was hard. I reached down and stroked
it through the material finally slipping my fingers
through the fly and squeezing his cock.

Up until then, I had been so busy concentrating on his
crotch that I had not noticed his shirt, which identified
him as a Theta-Chi, as … Read the rest

Exposed On the Road – A First Time Gay Sex Story

20 September, 2016 (00:05) | first time gay sex,, Uncategorized | By: Gaysexstories

by Goblinfeet (dr_mayhem@hotmail.com)

***

My first gay-experience was an innocent pick-up that
ended in public hardcore oral action. (MM, exh, 1st-
gay-expr, oral)

***

Although I consider myself straight, I did go through a
time during my early 20’s when I experimented a little.
This is a story of my first and still most interesting
bi encounter.

I had been drinking alone at a relatively well known,
if not popular, pub in the city of Adelaide. After five
or six drinks, I got to the point where I was getting
more tired than drunk. At about 1am I decided to call
it a night, and went looking for a taxi.

In a small but still populated city square, someone
called out to me. Half expecting someone I knew and
being drunk at the time I considered ignoring them.

“Want a smoke mate?”

I looked over and saw a man in his early 30’s sitting
on a bench smoking a cigarette. He was dark, with short
black hair, unshaven, though not in a scruffy way, and
tall. Taller than me at least. I must only be 5′ 7″ at
most and quite slim, with short fair hair. He held out
the … Read the rest