Date: Mon, 19 Jul 2010 14:04:21 -0700 (PDT)
From: briefs2999@yahoo.com
Subject: Losing My Cherry at 50!

This is a true story. It is intended for mature adults only. If you are
under 18, or are offended by stories of a graphic sexual nature or by
homosexuality, do not read this. Do not read tgis story if it is illegal
for you to do so where you live.

I have known I am bisexual since my early teens, I am sexually attracted to
both men and women.  For years I repressed my homosexual side, masturbating
to fantasies of guys, but doing nothing about it, never having any real
sexual contact with other guys. I thought I could be happy just fucking
women, but as I got older I longed to explore the other side of my
sexuality. Eventually, through the internet, I started secretly meeting up
with guys when I was out of town, away from people who knew me. For the
next few years I had many hot anonymous sexual adventures with guys, but it
never involved anal sex, which was I line I thought I would not cross. I
was ok with kissing, I loved making out, naked body contact, frottage and
mutual jack-off. If I really trusted the guy then maybe I would suck his
cock, and I loved getting my cock sucked by guys I was sure were clean.

One day I did "cross the line", I fucked a guy I had met online. We talked
about it and prepared for some time in advance. He was gay, but liked
straight or bi men. I decided to try anal sex as top just that once. We
made out in my hotel room, kissing and slowly undressing each other, Then
he got some lube and prepared his ass for me, fingering himself and lubing
himself. He got on all fours on the bed. I put on a condom and knelt behind
him. I grabbed his hips and pointed the head of my dick at his asshole, I
pushed, and bingo! My cock slipped easily up his ass. It felt good, but to
me it was not that different from fucking a pussy. I fucked him for about
10 minutes, gradually increasing the speed of my thrusts, then I ejaculated
into the condom in his ass. He jerked himself off while I did this, and
shot his cum on the bed. That was it, I never fucked another guy. And I
definitely never thought that one day I would let a guy fuck me.

As I got older I got more and more into sex with men. One day, while away
on a business trip, I met up with a gay airline pilot, "Jack". I was 50
years old by this time, Jack was in his late 30's. We met in my hotel room,
and that first evening we kept to the rules I set beforehand. We kissed, we
made out passionately, we got naked on the bed together, touching and
caressing and licking and kissing each other all over. We rubbed our hard
cocks together, I lay on top of him and we frotted together, humping
against each other, our bodies sliding and rubbing together as we kissed.
Finally we lay in each others arms and jerked each other off, stroking each
others cock till we shot our cum all over each other.  Afterwards we
showered together and cuddled naked on the bed.

This session was hot, but Jack wanted more. As we cuddled he kept admiring
my ass, looking at it, stroking it, kissing it. I am a runner and very slim
and I have a cute little bubble butt. He said he loved my little bottom, it
really turned him on and he really wanted to make love to me, to fuck
me. Finally I agreed to think about it, and we agreed to meet again the
next morning, when we both had the whole day free.

I thought about his desire to dick me up the ass all night long. Should I
try it? If I ever wanted to, now was the time. I really liked and trusted
this guy, he was handsome and hot, with a nice but no-too-big dick, and I
loved the way he got so turned on by the sight of my ass. Also, I knew he
would be very gentle and would respect my limits. Did I really want to try
having a penis in my bottom? Was I ready to let another man butt-fuck me?
Could I be a "bottom" for a horny top guy? Early that morning I emailed him
and told him to bring lots of lube and condoms, I was willing to let him
try to fuck me!

I was both excited and VERY nervous when Jack arrived at my hotel room. He
calmed me down right away, hugging and kissing me tenderly and telling me
that we were going to take things VERY slowly, we had all day and all night
to do this. We sat and kissed and he ran his fingers through my hair. Our
tongues met in our hungry, hot mouths and our hands explored each other
through our clothes. Soon we were ripping each others clothes off and
heading for the big, king size bed. We lay there together naked, and he
held me in his arms, kissing me and telling me how much I turned him on. I
knew it, I could feel his rock-hard cock pressed against my thigh! We spent
an hour just making out together, naked on the bed, fondling and caressing
each other, lightly stroking each others cock, each of us moaning softly.
He whispered in my ear that he longed to fuck me, to feel his cock inside
my tight little asshole, that he wanted to make love to me, to enter me, to
fill me up with his cock, to fuck me lovingly and gently.

Finally it was time to try it. Jack told me to kneel on the floor facing
the side of the bed, then rest my arms on the edge of the bed and lean
forward, lifting my ass a little. He took a big mirror off the wall in the
bathroom and positioned it on the floor next to the bed so that I could see
myself in it, and would be able to see him too. I would be able to watch
him fuck me! Jack knelt behind me. He caressed my ass, bent over and kissed
ot all over, murmering words of appreciation for my "beautiful little
ass". He caressed my ass crack, slipping his fingers between my ass cheeks
as he leant forward and kissed my neck and nibbled on my ear at the same
time. Next he took a tube of lube and very gently started to rub the
lubricant between my ass cheeks, deeper and deeper into my crack till he
reached my asshole. "Just relax Alex" he whispered softly as he
oh-so-gently massaged lubricant into my sphincter muscel with one finer.
He rubbed and rubbed and then he slipped one finger inside my asshole! It
felt good actually, warm and pleasant. He finger fucked me for 10 minutes
or so, gradually working up to 2 fingers in my ass, kissing me the whole
time and telling me how much I turned him on.

After fingering my ass for a while, he took his hard cock in his hand and
lay the shaft on my ass crack. He pushed a little and his boner slipped
between my lubed up ass cheeks. His dick was vertical in my ass crack, the
head of his dick pointing up at my bare back. He leant against me and
frotted his cock against my ass, wrapping his arms around me and playing
with my dick as he humped against me. It felt good to feel his big cock
sliding up and down in my crack, and it looked hot in the mirror!

Next he pulled back and took his cock in one hand. He undid the condom
wrapper and slipped the condom over his cock, then squeezed lube from the
tube all over it. I watched in the mirror nervously.  This time he pointed
the head of his cock right at the center of my ass. Slowly he moved
forward, pushing his dick head between my ass cheeks, pushing it further
into my ass crack till he reached my asshole. He stopped there, and just
lightly rubbed his dick head against the entrance to my hole. He rubbed and
rubbed, massaging my tight little hole with the tip of his big penis. He
whispered to me to relax again, and kissed me. "Are you ready Alex?" he
asked. I mumbled "yes Jack, but I don't know if I can take it, I.."
"Shhhhhh" he replied, kissing my neck again. Gently he pushed forward with
his hips.  We rocked together like that for some time, with him holding me
and gently pushing with his hips, his dick pushing at my back door, a
little harder each time. I thought I would not be able to do this, but he
was patient. He pushed a little harder as I got used to the feeling, then a
little harder, then harder, harder, harder....suddenly my asshole opened up
and the end of his cock penetrated right into me! I cried out and bucked as
a wave of pain hit me "oww fuckk owwww!"

Jack immediately withdrew from my ass and turned me around, a look of great
concern on his face.  "Did that really hurt bad?" he asked. I thought about
it. "Well it hurt like hell when your cock actually slipped into me, but
then a few seconds later I think it was OK" "Man your ass is so tight, I
don't want to hurt you" he replied. "Jack, it's OK, let's try again, I want
to try again, but don't pull out right away even if I cry out again!"

Jack was so worried about me that his dick had gone completely soft. I
pulled the condom off his limp penis and we climbed back onto the bed
together. "Lets take a short break before we try again" he suggested. I
agreed, then suddenly realized that I was hungry, It was lunchtime and I
had not eaten anything yet that day. "You want something to eat?" I asked
"Let's order room service and eat in bed!"  And so we ordered sandwiches
and drinks. When they were delivered I just wrapped a towel loosely around
my naked body as I went to answer the door. Jack discreetly slipped into
the bathroom.  The handsome young bellboy who delivered our sandwiches was
clearly flustered. The "Do not disturb" sign on the door, the rumpled bed,
sandwiches for 2, my nakedness beneath the towel in the middle of the day,
the condom wrapper and tube of lubricant on the nightstand...it was obvious
that two people were having sex here. Of course he might have assumed there
was a woman in the bathroom, except for the trail of men's clothes leading
to the bed, two pairs of mens shoes, kicked across the floor, two pairs of
jeans, two shirts in a tangled heap, two pairs of briefs in the middle of
the floor.... He actually blushed as he took in the scene, but I made him
walk right I and put the tray on the bed side table! Afterwards we cuddled
together and laughed about it as we fed each other our lunch.

We started again. Kissing, making out, stroking each other. He moved me
back to the floor, back to my position in front of the mirror. This time I
knew what to expect. He fingered my asshole and I loved it. He rubbed his
cock in my crack and I wiggled my hips, wriggling my bum against his
cock. Then I opened up another condom. "I'm ready" I said "put this on". In
the mirror I watched him slip[ the condom over his penis, then rub lube all
over it. He took his penis in one hand and guided it into my ass crack,
right up against my little hole. Then he gently started pushing again.

It was no easier the second time. It took a long time, pushing, pushing,
his penis probing and prodding at my anus, pushing a little harder, harder,
harder...suddenly it happened again! "Oh fuckkk oooww fuck, ohh oww..don't
pull out!" I cried in one stream of expletives and cries of pain and the
instructions for him to stay inside me! Jack kept perfectly still, the head
of his cock buried in my ass.  After a couple of minutes the pain subsided,
and I just had this warm, full feeling. "OK jack, push it in further, but
slowly!" I said Jack very slowly pushed forward, easing his shaft deeper
and deeper into my ass. It felt good! A bit uncomfortable, but good and
exciting and not painful now! Slowly he pushed his cock all the way up my
ass, till every inch was inside my, right up to the base. I felt his pubic
hairs against my ass cheeks.

Jack paused again, and let me get used to the feeling of his manhood deep
inside me. I felt filled up by him, possessed by him, taken by him, I was
his and I had him deep within me. Jack put his hands on my hips. Very
slowly he started to move, withdrawing his cock an inch or so, then sliding
it back in.  He was fucking me! I was getting fucked up the ass by a
handsome young pilot and I was loving it! I watched in the mirror as he
pulled out a little further, part of his hard, slippery, glistening shaft
visible between our bodies for a moment, sprouting from his dense Matt of
pubic hair and disappearing into my ass., He pushed back in, ohhhhhhhhh now
it felt soooo good! He increased the length of his strokes till he was
pulling almost all the way out of me, just his mushroom head still inside
me, then he would pause, then slowly slide his hard shaft all the way into
me, balls deep. He whispered "Oh Alex, your ass feels sooo good, I love the
feel of my cock in your ass, I love fucking you!" I replied "ohhhhhhh Jack,
fuck me, fuck my ass with your big cock Jack, oohhhh I love the feel of
your cock deep inside me"

Very gradually Jack picked up the pace, thrusting his hips a little harder,
thrusting in and out of me a little faster, then faster again. Soon I was
completely relaxed and he was fucking me good, his cock sliding in and out
of my ass, in and out, in and out, faster, harder. I watched in the mirror
as his hips rocked and bucked and he pounded my ass, fucking me harder,
ramming his cock deep in my ass.  "Oh fuckkk yess Jack, fuck me, fuck me
hard!" I yelled now, really getting into it. Jack was moaning loudly, and
breathing very hard "Ohh fuckkk Alex your tight little ass feels sooo good,
oooh oooohhh, oh fuck I love fucking you!" I reached between my thighs and
stroked my own cock a little as he fucked me, I noticed a little pool of my
pre-cum on the rug underneath me.

Suddenly Jack slowed down, then stopped. "Alex I don't want to cum yet,
let's make it last" he gasped, panting for breath. And I agreed, we had all
day and all night! Jack carefully pulled his cock out of my ass, then
pulled off the condom. My ass felt a bit sore, but basically OK. Both of us
were hot and sweaty, so we decided to take an erotic shower together. We
climbed under the warm water together and let it run all over us, then we
soaped each other up all over, caressing and fondling each other with the
suds. Afterwards we dried each other off, then we cuddled together on the
bed for a while, and discussed what we had just done together. Soon we were
both ready to do it again!

This time he led me over to the sofa. He Sat me on the sofa and knelt in
front of me, facing me. He lifted up my legs and put them on his shoulders,
and I lay back, my ass rotating into view for him.  Gently he lubed his
fingers and finger fucked me again, then he slid on another condom. I
thought it would be easier this time, but it was not, my ass had slammed
shut just as tight as before. And this position, though It meant I could
look into his eyes as he fucked me, did not present my ass tilted at such a
good angle for easy entry. We struggled for a while, he lost his hard-on
once and we had to slow down and go back a couple of steps. Then we tried
again, and tried and tried and he pushed and pushed and it was hurting a
bit, and just as I thought we would have to give up on this position "OH
FUCKK owww" he was in me again!

We fucked like bunnies on the sofa and he leant forward and kissed me as he
dicked me. I was his!  He was deep inside me and staring into my eyes. He
moved faster, faster, he pumped and pumped and pumped. We were both moaning
loudly again. We had agreed that he would not cum inside me, I was not sure
I was ready for that, so when he was almost at climax he pulled right out
of my ass and ripped off the condom. I reached down and grabbed his swollen
cock and stroked it hard and fast.  After just a few strokes he let out a
strangled cry and shot a big load of jizz all over me!

Afterwards we went back over to trhe bed. He held me in his arms and
stroked my cock while whispering in my ear what a great fuck I was, how
much he loved having his cock up my ass, how much he loved to fuck me. It
did not take long for me to finally reach my own huge orgasm. I shot a
fountain of cum high in the air, 4 feet or so straight up, and it splashed
down all over both of us. Wow!  That had been an incredible experience.

Afterwards my asshole was a little sore for a few days, but it soon felt
fine. Otherwise, no ill effects from the first butt fucking of my life. And
the only butt fucking I have ever had too. So far I have never repeated the
experience, I am still not sure if I ever will. But on lonely nights I
often masturbate while thinking about that big cock in my ass.......


If you liked this story or can relate to it let me know. Email
briefs2999@yahoo.com