Fun With Craigslist

Hi readers! I haven’t written in SO long, but I just
have the urge to share today. I hope you don’t mind,
and if you like the story, I hope you’ll drop me a

You probably don’t have time to search for my old
stories, so I will recap the basics here. I LOVE trying
on different personalities, and the Internet has always
given me an outlet for that. I have emailed and chatted
with many friends, and have met more than a few now in
person. I am also happy with my life, and do not want
to add any unnecessary complications. To combat these
problems, all of my personalities have one thing in
common all are married. Now in truth, I am not but
I am also not looking for a boyfriend online. (I am in
a serious relationship, and no, he does not have this
email address and he does not know some details of my
life. I know that isn’t nice, but it’s the truth.)

As my job requires a fair amount of traveling, I have
been able to express myself in more than a few ways
with a few special people. I thought I’d share this
particular experience. (I will not mention names or
locations just in case he reads this!)

Knowing that I was going to have to be in (some place
🙂 for a few days in August, I posted an ad on
craigslist in late June. (I know that part can be
maddening, but I really need to chat for a while before
I am willing to meet someone in person.) The ad’s title
was simple ‘mww looking for something and someone
special.’ The body of the text was also simple ‘I’m
looking for a beautiful man, someone fit, someone
unafraid to shower at the gym. LOL!’

I know this last part was shallow I don’t normally
post for well-endowed men, but this was part of this
particular fantasy. I received a huge number of
responses and replied to a few dozen of them. (Hint
guys, respond with a normal, non-pornographic photo and
write a few paragraphs!) After chatting for a few weeks
I was down to a single man. (Most guys get bored of
chatting unless its cyber, and I VERY rarely do that.)

And this single man was, in fact, a single man! He was
just 20 and still in college. From his photos and words
I could tell that he was special. He wasn’t very tall
(5’10”) but was quite fit and very funny. He was also
very patient with me and was willing to take things at
my pace.

Here is what I told him. I told him I was married and
that over the course of our marriage my husband had
become curious to see me please another man. In
particular, my husband wanted to see me meet, seduce,
and orally satisfy a stranger. I further told him that
the idea scared me and that I worried that things could
get out of hand very fast. I shared with him that the
very concept of a stranger is what scared me most,
because there are so many unknowns. I also let him know
that I had hoped that if I did this once, my husband
would realize that he didn’t really want to see that
ever again.

He asked why my husband wanted this I told him I
really didn’t get it. He asked why my husband wanted to
keep it to oral sex I told him we were trying to get
pregnant. He asked why I chose him to chat with I
told him it was because he was kind, funny, and cute.
He asked why I might choose to meet him I told him
that I thought he would make it clear to my husband
that he didn’t want to see that again. He pressed me on
this, and I confessed that my husband was of modest
proportions and that I felt that it might disturb him
to see me with a young, handsome, fit, black man. He
seemed fine with my answers.

During our chats he confessed that he fantasized about
married white women, and gently bragged that he was not
of modest proportion! This, of course, was very cute
and kept me giggling during our chats. We agreed to
meet at a local caf near his University.

When I arrived he was already seated in a booth with an
open window. He was dressed beautifully a pressed
white button down shirt with pleated tan pants, and a
black belt and black shoes. Very respectful! I dressed
playfully in a knee length teal v-neck dress with
elastic shirring and white wedge sandals. We smiled I
think we were both happy with what we saw.

James might have been extra happy, to tell you the
truth. Up until this point he still had not heard my
voice or had seen my picture. It was reaffirming to see
that he found me attractive. My looks are more girl
next door or maybe tomboy than anything more glamorous,
and my body is still fairly athletic. (I was a swimmer
in high school and college.) I’m 5’3″ and currently
weigh about 115 lbs certainly more than when I
competed, but not unsightly. I play-up the tomboy look
by wearing very little make-up and having a retro-
bobbed hair cut. I think the cut actually looks better
on brunettes, but I don’t want to dye my hair again!

We chatted about any and everything for an hour or so
over coffee. He was so sweet! I know he wanted to
discuss ‘the event’ but he just didn’t seem to know how
to bring it up. (For my part I was just enjoying the

Finally we turned the conversation to what was supposed
to be a random meeting with my husband present. We
discussed the logistics how, when, and where and
discussed secrets. In particular, he was not to
approach me, or act as if we had met before. This was
also very important I told him my husband would not
want us to be affectionate. He should not be trying to
hold or kiss me in any way.

We agreed that this was strange, and hard to do! In
fact, I confessed, that that was the hardest part of my
husband’s fantasy. That I am NOT like that, and that
that made the stranger aspect more difficult. It was
because of that that I needed to meet the man first. He
completely understood.

He also understood that I wanted this to be a one-time
thing, so that my husband would never ask for it again.
(As you might have guessed by now, I was totally
enjoying this game but was not sure where it would end
up remember, I do not really have a husband!) He
smiled and said that he would be happy to make him
jealous, and offered to prove it right now. I told him
that I trusted him and that it wasn’t necessary.

James assured me that it was and had me move from
across from him to next to him in the booth. As we
casually talked he took my hand and rested it in him
lap. He held it there firmly as I burst into laughter!
(I KNOW laughter was the last thing he expected.) I
couldn’t help it it just struck me funny that he was
so big. Really he was kind of freaky large.

It is hard to describe what it felt like, but I guess
its fair to say that it was like a warm, jelly-filled
tube sock. (Wow that sounds SO unsexy!) We laughed
together for a bit and he removed his hand from mine. I
left mine where it was. It was very exciting to feel
him grow. We agreed that this would cure my husband of
his fantasy!

He told me that before he would agree to do this for
me, I would have to go back to his room with him. (That
solved the husband problem!) I asked why, and he
mentioned reasonably that he feared that this could
be a set up, that he could arrive and be put into
danger. And, of course, that his fears would be
alleviated if we could practice the night just once!
(Such a very bad, good boy!) I laughed again, and
agreed! But cautioned that I didn’t have much time. (In
truth, I had about 6 hours before my airplane

He paid, we left, and we walked fast to his room. I
tried to convince him that I hadn’t cheated on my
husband before and he said that he really didn’t care.
He was very honest he wanted to know what that night
was going to be like, and he wanted to know now.

I was relieved that he lived in an apartment and not a
dorm. He opened the door to a very modest, but very
clean, living room. He said not to worry that he lived
alone. He pressed me into the door and used my body to
close it. ‘Just to make sure I understand,’ he said, ‘I
cannot do this.’ And then he kissed me. It was a
perfect kiss! Soft and gentle at first, just a slight
hint of a tease with his tongue, and then deeply. He…
was… gorgeous!

When we broke I said yes, that we couldn’t kiss. ‘I
also can’t do this, right,’ he said as he cupped my
breast and began kissing my neck. ‘No not that
that’s correct,’ I barely got out as he continued to
touch and kiss me. He was so perfect, and so loving,
and had me so excited so quickly! With his left hand he
pulled my dress up so he could hold my butt while he
pressed his body into mine. I felt small but safe in
his hands.

I was saddened when he broke our embrace. ‘But I am
allowed to show you this,’ he said as he started to

‘Yes you can,’ I said, ‘but you can’t get all the way

But he did anyway, and he was marvelous. His body was
muscular, his legs powerful, and his penis spectacular.
He was so proud! He smiled and said, ‘Follow me if
you’re interested, but do not come into my room if you
are dressed.’

I watched him walk down a hallway and into a room. I
stood at the entryway and said, ‘You know this isn’t
part of his fantasy.’

He said, ‘I know, but it is mine. Are you coming in or

It might have taken me 15 seconds to undress, drop my
cloths, and jump into his arms. ‘Are there any other
details of this fantasy that I should know?’ I asked.

‘Just be honest, deal?’

I said it was.

‘Have you been with a younger man before?’

‘No,’ I lied.

‘Have you been with a black man before?’

‘No,’ I lied again.

‘Have you ever been with a man this large?’

‘No,’ I said, but this was pretty close to the truth!

‘Then this is my fantasy!’ he said, and I kissed him.

We kissed and lay in each other’s arms for a while, and
got used to being naked with each other. And when he
pulled my hand to his penis, I knew the relaxation was
over. ‘Come on, girl, show me what you can do in front
of your husband. And then I’m going to show you some
things he can’t do!’

He groaned as I took his head into my mouth and closed
my lips tightly around him. In truth, I love doing
this. I always feel in control, and kind of powerful,
with a man in my mouth. I took him in as far as I could
while firmly, but very slowly, stroking him with my

Before I could pick up the pace, he pulled me on top of
him and began to taste me. I am not usually a great fan
of 69 because I am very sensitive, and my own pleasure
can make it hard for me to concentrate on my job. But
this was fantastic! He used his tongue expertly on me,
and although I was ready for him back at the caf
(kidding, almost!) he now had me going crazy.

He teased me to the point of exploding, and then pushed
me down his body. ‘Show me how much you need me girl!
Get up on your man!’ And I tried. I rested my hands on
his knees and moved myself across his length. When he
was aligned, I arched my back a little, and pushed down
on him. I lost it after his head entered me, but he
grabbed my hips and kept me on track.

‘You like that, don’t you?’ he laughed. ‘Well you are
going to love this.’ And with that he pushed deeper
into me.

It’s hard to describe the feeling properly, but he felt
huge, I felt complete, and I knew I was needed. He made
love to me completely, and forcefully. I was already
gone, and he didn’t last long like this. When he pulled
my hips down and held them in place, I knew he was
ready. I also knew this was his fantasy, so I told him
to be careful AFTER I felt his first spasm. He had no
intention, and I didn’t fight him.

‘That was amazing baby,’ I whispered, ‘but I should

‘Not yet,’ he said as he rolled me over. ‘This is why
you need a young man,’ he teased as he placed his still
hard penis at my entrance. He pushed back into me and
kissed me deeply as I wrapped my legs around him and
let him take me. And he did, slowly and deeply for
almost 20 minutes. I was in orgasmic heaven for most of

‘And this is my fantasy, girl,’ he said, ‘Ask me to cum
inside you again.’

‘Please cum inside me, James, I love you,’ and with
that, my young lover exploded again.

I showered and left, promising to email him and set up
a time to make my husband’s fantasy come true. But I am
sure that you have already guessed, I never emailed him