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rm_diaryteller
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Diary of my affairs. Chapter 5. My first anal experience

Once it was clear that Wayne and I were both interested in
being more than just friends, we had sex of some kind practically
every day as if we were making up for lost time. It was anything
from blowjobs when I was on my period to all day long Saturday
marathons. Wayne never used a condom and always pulled
out mostly cumming on my stomach, tits or back. I’d only
let him cum on my face in the shower for a long time after he
gave me an unexpected facial the first time I blew him that
I covered in chapter 4. The only times he didn’t pull out
was when I was sucking him. He loves cumming in my mouth just
as much as I love getting my pussy ate. At the time we were
probably leading the world in oral sex scenes and did way
more oral than actual fucking. Of course the conversations
written in here are not exactly word for word since it was
so long ago, but they’re as close and as accurate as I can
remember!





After about a month of fucking and sucking like nymphomaniacs,
I found out a few things. Wayne was like my first boyfriend
Bob in the fact that he liked for me to squeeze his balls as
hard as I could only to immediately let go. He also liked
for me to bite his dick. The difference was Wayne would ask
me questions while I sucked him like asking me to bite if
I wanted him to cum in my mouth or something else because
it turned him on if I bit him.


I also started noticing what seemed like a jealous streak
in him. Every time he’d see me talking to a guy he’d start
asking questions. He never seriously got upset always
asking in a nonchalant kind of way, but I noticed and was
actually happy knowing he was jealous or thinking he was,
but I never did it on purpose!


One night during the heat of the moment I made the mistake
of telling Wayne he was the first guy to ever cum in my mouth
and he started asking about my past sex life wanting to know
who I’d fucked and what I’d done but I refused to answer.
I’d learn it was a turn on for him to hear about those things,
but for the time being I wasn’t about to tell him anything,
especially going into details of who, how, when, where
and how many times. Sometimes when he brought it up it pissed
me off, and I’d tell him it was none of his business, but
sooner or later he’d ask again.


Then one night we were at his place with me blowing him when
he said, “I don’t mind pulling out when we fuck but I
want to cum inside you.”


“Use a condom, ” I replied since I wasn’t on the pill
and thought I knew what he meant.


“It’s not the same as cumming inside you.”


“You cum in my mouth all the time, ” I said thinking
he wanted cum in my pussy. I was wrong about that, but I was
about to find out what he really wanted.


“I talking about anal, ” he said catching me entirely
off guard.


“I don’t want to do that, ” I said knowing how much
it hurt when my old boyfriend Joe unsuccessfully tried
it. Wayne’s dick was just as thick as Joe’s, but Joe’s
was a lot longer.


“Have you ever tried it?”


I didn’t answer so he asked again and I rose up asking,
“Do you want me to give you a blowjob or do you want to talk?”



“Lay down and I’ll eat you so you can tell me about it, ”
he said getting up.


“Tell you about what, ” I asked?


“Anal, ” he replied diving between my legs to start
eating me while asking more questions.


Other than only saying he was the first guy to cum in my mouth
it would be the first time I ever talked to him about any of
my previous sex affairs. Still wanting to keep as much of
my past sex life to myself as possible while he ate me I took
a deep breath before saying, “One of my old boyfriends
tried it, but it hurt too much.”


Suddenly Wayne wanted to know more about it along with what
I did with every other guy I fucked. Since it seemed strange
to me I told him very little. I’d never asked about his
past sex life because I wasn’t interested in it, and I
couldn’t understand why he wanted to know about mine.
He kept trying to get more information, so I finally said,
“An old boyfriend of mine might have gotten the head of
his dick in my ass before I jumped away in pain.”


“You don’t know if he got it in?”


“He got it far enough that I jumped away because it hurt.”



“Who was it?”


“Are you going to eat me or ask questions all night, ”
I asked getting a little pissed? However, a few years later
I would tell him it was Joe who he didn’t know at the time.



“Tell me some more about him, ” he said, going back
to eating me.


“Well for one thing he was so proud of his dick that the
first time I fucked him he had me measure it and when I did
I found out he was just over nine inches long, but he wasn’t
any thicker than you are.”


“Did he use any lubrication?”


“He used spit.”


“He probably didn’t use near enough. What else exciting
did you do with him and other guys?”


“I deep throated him one time hanging my head over the
end of the couch, ” I said refusing to tell him anything
about guys other than Joe.


“Was he hard or soft?”


“He was hard as a rock.”


“So you had a few inches in your throat?”


“It took me a while to do it, ” I admitted going on to
tell him how it came about explaining the trial and error
process of finally deep throating Joe that I covered in
chapter 2. I could tell Wayne loved hearing it and to be honest
it turned me on telling him.


“How did you feel when you deep throated him?”


“It made me horny as fuck. He started mouth fucking me,
and I was hoping he’d cum, but he pulled out to fuck me before
he got off.”


“I’d still like to use some petroleum jelly and cum
in your ass instead of shooting all over your stomach or
back.”


“Shut up and eat me and I’ll think about it, ” I said
to his delight.


For the first time that I can remember he ate me off only using
his tongue the whole time and never did finger me. Hoping
the petroleum jelly would help I agreed to let him try anal,
but I thought I made it clear that if I said to stop he’d
stop!


Naturally he agreed but said, “If I get my cock all the
way in your ass and you stop me before I’m done it’s just
going to piss me off.”


Understanding where he was coming from I reluctantly agreed
and knowing if the petroleum jelly helped I might be in for
a full ass fucking, I said, “If you can get balls deep I’ll
let you do it as long as you don’t slam it in. But if I tell
you to quit before then you have to take it out.” Showing
his appreciation he stayed where he was and drained my pussy
dry eating me off a few more times before getting up and standing
by the bed.


“Come over here and suck the cock that’s going to fuck
you in the ass.”


Getting in position I sucked him while he asked me a bunch
of questions wanting me to bite if the answer was yes. He
also mentioned how it would be a lot easier with petroleum
jelly instead of spit and I was hoping he was right. The last
question he asked was if I was ready and feeling horny and
hoping he was right about the petroleum jelly I bit him hard
hoping that anal wouldn’t be too painful.


When he was ready I watched as he grabbed the jar and stuck
his dick in it getting a big gob on the head of his dick. Then
after getting me doggie style on the bed with my feet hanging
over the edge he had me spread my knees apart to lower me until
we were lined up. Feeling the cold petroleum jelly touching
my asshole I gritted my teeth followed by feeling him trying
to push hid dick in. It hurt, and I ended up jumping away a
few times before he finally got the head in my ass. When he
got that far he stopped to let me get used to it and teased
me saying, “You know I’m going to fill your ass with
cum.”


It felt weird, to say the least, and after a minute or two
I felt him slowly pushing it in causing me to moan like crazy.
I wanted to tell him to take it out, but since he stopped on
his own I just kept gritting my teeth.


When he finally started slowly pushing deeper I asked him
not to move a few times, but he just waited about a minute
before pushing some more. After maybe a total of five minutes
after getting the head in my ass I felt his body pressed against
mine meaning he was balls deep in my ass and knew I was about
to get ass fucked for the first time.


As if he needed to he let me know he was balls deep, he started
talking dirty while leaving it there for a minute or two
saying, “It’s all the way in. Just let me know when you
want it.”


After maybe a minute and before I said anything he started
to slowly back away saying, “This feels awesome.”
I thought to myself maybe it feels good to him, but my first
ass fucking wasn’t doing anything for me and it still
hurt!


I was hoping he’d get off quick and get it over with because
I was almost in tears from the pain I was going through just
to satisfy his wish of cumming inside of me. Every time I
felt him move I grimaced and moaned while clenching my teeth.
I almost told him to take it out, but I knew it would piss him
off and only asked him to slow down or stop a few times pretty
much letting him do his thing trying not to bitch about it
too much.


When he sped up his pace I started moaning nonstop, but he
slowed back down a minute later saying, “I can't
believe how tight your ass is! This is fucking Awesome!”



Being more turned off by getting ass fucked than turned
on by it, I wasn’t anywhere close to cumming, but he kept
speeding up from time to time only to slow back down when
suddenly he went so fast that I was screaming instead of
moaning causing him to stop.


After a while I wasn’t in as much pain as I was at first,
but I wasn’t comfortable either. No longer slow fucking
me anymore he kept a steady pace going until he finally said
he was close to cumming and started fucking me harder as
if it was possible! It hurt, and I’d have asked him to slow
down but knowing he was close I wanted him to hurry up and
cum in my ass and get it over with.


The next thing I knew his hands were wrapped under me a little
on the sides of my stomach when he started thrusting forward
while pulling my hips to him fucking my ass as fast as he could
go. Pummeled, drilled, pounded, hammered or even plowed
doesn’t even come close to describing the ass fucking
I was getting.


“Are you ready for me to cum in your ass, ” he asked?



Managing to get out a painful, “Yes, ” I wanted to get
it over with! Hearing the sound of his balls slapping against
my pussy with every stroke, he started off like he was trying
to make love to my ass, but he sure as hell wasn’t now! Feeling
like my ass was on fire, I kept moaning out loud in pain, and
he never once asked if I was ok. He was on a mission, and I knew
it wasn’t going to stop until I had cum in my ass!


Suddenly he pulled my hips to him squeezing them even harder
and stood there leaving his dick balls deep and let out a
loud moan as he started cumming in my ass as deep as his dick
could shoot. My first ass fucking was finally over with
and feeling relieved when he pulled out I went straight
to the bathroom trying to lose some of his load.


“Are you ok, ” he asked as if he really cared when I returned?



“Yes but don’t plan on getting anal again anytime soon, ”
I said making him eat me off again.


Then seeing him start to climb up to fuck me, I said, “No,
not yet!After what you just put me through I want you to eat
me until I’m ready to fuck!” Purposely making him eat
me off a few more times, I didn't give in until I was tired
of hearing him asking to fuck me.


Wayne had quite a few other times where he asked for anal
offering that I could be on top and in control, but I kept
refusing. I just told him to put on a condom and cum in my pussy.
He also offered to pay for my prescription if I’d go on
the pill, but I declined at first.


About a month before my birthday he asked if I’d like to
go on vacation to celebrate it, and I said yes if I could get
off work. It didn’t hit me right away, but once I remembered
that he was planning on proposing to his old girlfriend
Debbie on her birthday I got excited. Luckily for me they
broke up a few weeks before her birthday. We were in love
and I was prepared to say yes thinking he might propose while
we were on vacation. Even though we’d only been actually
dating for a few months, we’d known each other for about
three years. Marrying Wayne had crossed my mind a few times
back then, but I couldn’t tell if he was thinking about
it.


As it turned out it was him who couldn’t get off work, but
just for another month. The very first night on vacation
we were in the hotel fucking with him on top of me when he said
he was ready to cum. With me being close to cumming too, I
told him not to stop and wrapped my legs and arms around him
not wanting to let him go knowing I was taking a risk of getting
pregnant, and I’ll never forget the conversation that
followed.


With my legs wrapped tightly around him, he continued fucking
me and asked, “Will you marry me?”


I said yes, and he started fucking me even harder until his
cum was splattering the inside of my pussy sending me over
the edge as I started cumming like crazy. I always imagined
being proposed to by a guy on his knees as opposed to while
I was getting the fuck drilled out of me!


As it turned out I didn’t get pregnant, at least not that
time and the next day we were off shopping for wedding rings
and eloped while we were there.


My next chapter will be about flashing my pussy while we
were still on our honeymoon.


Thanks for reading,


Mary


importentman2
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amazing story Mary. Very erotic and sensual. Your realty
description is fantastic

rm_diaryteller
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quote importentman2:
amazing story Mary. Very erotic and sensual. Your realty description is fantastic
Thanks, writing them as I remember them is easy but with
it being so long ago the quotes may not be exact, but they're
close enough.

ffrankn805
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You capture the essence of your experiences and feelings,
both painful and not so painful... all amazing!


I'd love for you to post some pics or videos of you taking
a load in your mouth or your ass

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