I guess I should start from the beginning. Jon and I had
been together for a while. Life was good. He treated me
well and I loved him. One day we started talking about
our exs. I learned that he had a pretty wild
relationship before me. He is older than me. I am 23, he
is 29, so I knew he’d had previous relationships. I just
didn’t realize how wild the sex with this ex was.
We had a great sex life, but nothing like he described.
I’d only had one other partner before him. I mean, I’m
pretty. At 5′ nothing and 100 lbs, I get a lot of
attention and I love it, but I never acted on it.
As we talked about fantasies I admitted I had a thing
for older men. He asked if that’s why I chose him and I
admitted that was part of it. Then he asked me how old.
I told him there were guys in their 40s and 50s at work
that I was attracted to. He pressed me on how attracted.
I finally admitted I fantasized about them sometimes.
I thought he’d be weird about it. Instead he got all
excited and told me that was hot. Next thing I knew we
were fucking like rabbits with him asking me about the
older guys and what I imagined doing with them. It was
wild intense sex and I came like crazy.
A few days later we started talking about fantasies
again. I asked him why he liked the fact I was into
older men so much. He told me he had a fantasy of seeing
me with another man and the idea of it being an older
man was even more exciting.
At first I thought it was an odd fantasy, but I loved
him and since it was just fantasy, I thought I’d indulge
it. I asked him more about it. He started showing me
stories online about women with other men. They were
from a man’s perspective. They talked about how much
they enjoyed seeing their wives or GFs with another man.
Even doing things with the other man she would not do
As we read the stories I admit I got turned on. I could
picture me and some of the older men I knew. I could
picture letting them take me in front of my boyfriend.
We started incorporating this into our sex. I admit
having sex with my boyfriend describing how I’d look
with another cock in me, or how he’d like to watch me,
made sex much more intense.
One day he suggested we try to make the fantasy real.
Real? No way, I thought. I had excuses. Who would we
get? How would we choose him? I would never do it with
someone I knew.
What I realized was, I was turned on by the idea but the
logistics bothered me. My boyfriend suggested we try
craigslist and see what we found. At worst we’d get some
laughs out of it. I agreed.
He placed the ad. We did not have to wait long. We got
tons of responses. A lot of one liners. A lot of cock
pictures. I let my boyfriend weed through them.
Eventually he found a few that stood out. I did not read
them but he starting corresponding.
One of the guys really piqued my boyfriends interest. He
started writing erotic stories. I would have thought he
just copied them from somewhere except they were kind of
specific to us. Jon (my boyfriend) would show me the
stories and I would read them aloud to him. Not
everything in the stories turned me on, but I have to
admit reading them, knowing someone had written them for
us, and describing situations we fantasized about was a
turn on. The story reading always led to great sex.
Jon mentioned he was going to start calling some of the
guys he picked out. I did not want to look to
interested. The idea of making it a reality both
frightened me and turned me on. Jon did not push it. Jon
asked if there was a picture he could send out. I found
one that was fully dressed but really showed off my
figure. With the face cropped out, I told him he could
send it. The idea that he wanted to show me off to
strangers was a turn on. I wondered what they thought.
One day Jon brought up the guy who wrote the stories. It
turns out Jon had talked to him on the phone and thought
he sounded perfect. I was skeptical. Jon started by
showing me pictures. He was not gorgeous but he was
certainly attractive. Jon told me how much the guy liked
my pictures. It made me feel good to know he thought I
was hot. Then Jon and I started discussing the stories.
Jon asked me what I liked and didn’t like about the
In talking about the stories I could see me in parts of
them. It also made me think about the man who wrote
them. This guy obviously understood that sex was not
just slam me on a mattress. His stories showed
engagement, thought, and included me and Jon. I started
wondering what this man would be like in person.
Jon would tell me about his interactions with the man.
It became clear this was the guy Jon thought would work.
He sounded nice, I liked his stories, but I did not know
what the next step was. I certainly wasn’t ready to fuck
A few days later Jon asked me if he could take a picture
of me to send the guy. I told Jon to send one of the
pics he has. Jon said the guy had asked for a candid
shot. Here it comes I thought. The guy wants naked pics,
but no, Jon said he just wanted pics that were taken
just for him. In fact he said he didn’t want anything x
or r rated.
I thought about what I was wearing. I was in a pair of
tight shorts and a T shirt. What the hell. I let Jon
take the pic. Almost immediately the guy responded. He
thanked both of us for the picture and said how pretty I
was. He hoped he’d get a chance to meet us. I was
flattered by the compliments. After all, it’s nice to be
admired. I smiled at Jon and Jon joked that the man had
A few days passed and Jon asked if could take another
picture. I thought about the first one. I liked the
compliments. I kind of liked the idea of being shown
off. I said sure but told Jon to wait a minute. I went
From the letters and the stories I knew what this guy
liked. Short flirty skirts. Lacy tops. Cute shorts or
jeans with a top that showed a of leg and a lot of
belly. Well I had plenty of clothes like that. I also
knew he liked cute lacy thongs and boy shorts. Well, I
knew that wasn’t going to Happen. I also realized if I
went through with this eventually he’d see a lot more.
The thought kind of excited me.
I went to my closet and found a cute short sundress. The
dress covered me so I skipped the bra. I looked in the
mirror. I looked pretty, not sexy, not slutty, but
pretty. For fun I messed up my hair a bit. Now I looked
like the girl next door who just did something naughty.
Perfect I thought.
I went out and showed Jon. I did a little spin.
He said, “Wow, you look great.”
I liked the compliment.
Jon said “I can’t wait to show Dave what a hot
girlfriend I have.”
The thought of Jon getting excited by showing me off was
really turning me on. I wondered if Dave would like the
pictures. I realized that I really wanted him too.
Jon started taking pics and I started posing. Hand on
hip, turn around look over my shoulder. That kind of
thing. In one I let the shoulder strap of the dress
slide down my arm a bit and showed off a little of the
top of my tits. On another I held my leg out and pulled
the hem of my dress up to show off my entire leg and hip
stopping just short of my panties on my hips.
Jon was encouraging me. Telling me how sexy I was.
Telling me what a naughty girl I was taking pictures for
man I’d never met. It was all turning me on. We sat down
and went through the pictures. We sent Dave 5. We got a
response almost right away.
He started off telling me how sexy I looked and how
lucky Jon was. Then he went to each picture and told us
what he liked best. He liked that I wanted to take pics
and show off for him. He said he also liked my naughty
All this was too much. I unzipped Jon’s pants, straddled
his cock. Pulled my thong aside and just started fucking
him. Jon started talking to me.
“So you liked showing off for Dave. I bet you’d like to
show him how naughty, even slutty you can misbehave.”
He told me that Dave had sent him a cock pic and that
Dave was big and thick. He kept on telling me how much
he’d like to see that big cock split my pussy. I could
see it in my head. Fucking Dave, feeling full, watching
Jon. I Came. A great orgasm. So wet I had to throw both
the panties and the dress into the wash. Next day when
Jon was at worked I sneaked a peak at his email and
found the picture of Dave’s cock. It would definitely
fill me up.
One day I was putting on a cute thong. As I did I asked
Jon if he thought Dave would like them.
Jon responded with, “Let’s see.”
He took a few pics from the waist down of me in my thong
from the back and front.
Again the response was quick. Dave said he loved the
thong. He complimented my ass and my legs. This time a
bit more forward. He said he wanted to rip the thong off
me and for me to wrap my legs around him while he fucked
He said he could picture me on my knees, face down on
the bed, ass in the air, the thong pulled down over my
ass but still wrapped around my thighs and him plunging
his cock in me from behind. Both those images went
through my mind. They both made me tingle. I could see
that as I read the responses out loud Jon was getting
After that we took pics every few days. It definitely
turned us on seeing the responses. I would show off my
dresses. I would sometimes pull them up to show off the
panties I was wearing. One time I took pictures in just
a wife beater and a thong. In a couple I was pantiless
in a dress. I would pull the dress up to show off my
Taking the pics turned me on. Knowing I was turning on
this stranger and Jon was a win win. Jon and I fucked
almost every day. He would tell me what a sexy slut I
was. I was loving it when he said it. He would say he
couldn’t wait to see me give away my tight little pussy.
I told him if he was good I might let him watch when I
The weekend was coming up. We had no plans Saturday. Out
of the blue Jon said, “Let’s meet Dave.”
My stomach fluttered. This is the guy we’d been
fantasizing about. This is the guy I’d been showing off
too. He’s the guy that owned that big cock.
I knew I should say no, but I said, “OK.”
That night Jon and I fucked like never before. He kept
telling me what a slut I was for even considering
meeting this man. Telling me how he wanted to watch me
get fucked. How he wanted to see my lips wrapped around
that big cock. All those images were going through my
head and I was loving them.
Saturday came and I was like a schoolgirl on a first
date. I was pretty sure nothing would happen our first
meeting, but still. I was looking for something to wear.
I picked out a pink and purple lacy thong. One of Jon’s
Jon came in the room and said, “I bet Dave will love
I thought about Dave seeing them. I put them on. I
wasn’t sure on a bra.
Jon chimed in, “Don’t wear a bra. I want him to see
those sexy tits.”
I realized I wanted him to see them too.
I pulled on a short skirt. It stopped an inch below my
ass. It was loose so it flounced when I walked. For a
top I picked out a short sleeve v necked pullover. It
was loose enough that if I leaned forward you could see
Jon grabbed me, kissed me, and told me I looked hot. He
said he couldn’t wait to be out with me and show me off.
I was feeling sexy as hell. I knew strange men were
going to be checking me out and that one of those men
actually thought I might fuck him. I was already wet.
We got in the car. The plan was to meet Dave at a local
bar. As I sat I noticed how much my skirt slid up. If I
moved even a little my panties would show. Jon moved his
hand to my panties, pushed them aside and started
playing with my pussy.
“Wow,” he said, “What’s getting you so wet.”
I just blushed. Truthfully, my mind was already back
home with Jon and Dave getting fucked. Hard. I know I
probably wouldn’t do it, but that’s what I was thinking
We pulled into the parking lot, parked, and started
walking towards the door. My legs felt uneasy. I was
hanging onto Jon. I felt like running but knew I didn’t
We entered the bar. I looked anxiously around. The bar
was not full. I saw Dave sitting in a booth. We walked
over. Dave stood up to introduce himself. Next to me he
seemed big. He had a big chest and shoulders. He was a
head taller than me. My eyes were at his chest height. I
had to look up to talk to him.
He shook Jon’s hand. He then looked at me and said, “you
are 1000 times sexier in person.”
I liked the compliment and thanked him.
He said, “Can I see the back? I am a total ass man.”
Without even thinking I turned around. I was looking
straight at Jon. David said over my shoulder. “Your
girlfriend has a sexy ass. I hope I get to see more of
I wondered what Jon was thinking.
Dave put his hands on my shoulders, kissed my forehead
and said “you look amazing”.
To both of us he suggested we sit. I looked. The booth
he had chosen was a rounded bench around a table. We all
had to slide in. I slid in first, Dave on one side of me
Jon on the other.
The conversation actually flowed easily. Dave was funny,
smart, attentive, but not creepy. He made me laugh while
throwing in a ton of compliments. With each compliment
he got a bit more intimate. Some compliments were to me.
Some were to Jon about me.
I actually felt hotter when he talked to Jon about me. I
felt like someone who was going to be used and did not
have a lot of power over it. The idea excited me.
As we chatted Dave would touch my arm, my hand, my
thigh. Each time he touched me I felt a jolt of
electricity. As we talked his hand focused more and more
on my leg. I looked at Jon. Jon also saw where Dave’s
hand was. Our eyes met. We both knew I wasn’t moving
Dave’s hand. We both looked at Dave. He knew we were
giving him the go ahead. He commented on how soft my
thighs were. I thanked him and subconsciously spread my
legs a bit. His hand slid up and down my leg grazing my
pussy with each stroke.
It was all driving me crazy. I decided to go to the rest
room to breathe. When I got to the rest room I leaned
against the counter and breathed. The reality is my
panties were soaked. I could see my nipples hard against
my blouse. I straightened my clothes and exited the rest
room. Dave was standing there.
All I could say was, “Hi.” and shyly look at the ground.
Dave put his hand under my chin and said, “You are
sexier than I expected. Fucking you would be a gift from
I was shocked. All I could say was, “thank you”
Dave said, “I’ve been dying to see those panties you’ve
been flashing all night.”
He stepped back from me. Looking me in the eye he said,
Being told what to do made my heart beat faster. We were
standing in a hallway in front of the restrooms. Anyone
could have walked by. Even knowing that I reached for
the hem of my skirt. I pulled it up to my waist.
He said, “Nice.” and then motioned for me to turn
around. “Very nice,” He said.
He took my arm, turned me to him and pulled me into his
arms. I felt small in his arms. He looked down at me and
kissed me. I kissed back. His hands dropped under the
hem of my skirt and cupped my ass. As we kissed I
wiggled my ass against his hands.
The kiss ended and we walked back to the table. Dave had
his arm around me the whole way.
Dave looked at Jon and said, “I have a room across the
parking lot. I’m taking your girlfriend. Would you like
It sounded odd but the truth is I was going. I liked the
way he said “your girlfriend”. I hoped Jon would come
We all headed over to the room. As soon as we got in
Dave kissed me. Jon was right beside me. Dave nodded his
head that way. Still in Dave’s arms I gave Jon a
Dave then pulled my top off. Slowly he bent over and
started sucking on my nipples. This was the third guy
who’d sucked my nipples. This time my boyfriend was
watching. It was surreal and hot.
Dave looked at Jon, “Is she a good cock sucker?”
Jon said, “yes.”
Dave looked at me challenging me to prove it. I slipped
to my knees, unzipped his pants and started sucking his
Jon went and sat down. All the time I was sucking his
cock Dave asked me questions or talked to Jon. It felt
odd but exciting. I felt like a sex toy. In fact at some
point Dave called me a slutty little fuck toy. I liked
He’d tell Jon how good I was, ask if Jon liked watching
his little slut suck cock, and tell Jon how lucky he was
to have this sexy little slut as his girlfriend.
To me he would ask if I liked his cock, did I like
sucking it in front of Jon, how did I feel on my knees
with a strange cock in my mouth.
I was getting off on answering his questions and
listening to Jon answer. I felt free. I felt I could do
anything. I could be as slutty/naughty as I wanted and
no one would judge me. I was loving having this strange
cock in my mouth.
Dave pulled me up to my feet. He stood behind me. I was
Dave said, “Take the skirt off.”
I unzipped it and let it fall to the floor.
Next he told me to walk over to Jon. I walked over in my
heels and thong. When I got to Jon, Dave said to Jon “if
you want me to fuck Your girlfriend take her panties off
I was looking in Jon’s eyes. I was hoping he’d do it and
hoping he wouldn’t. He reached out and pulled my thong
slowly over my legs.
He then looked at Dave and said, “Fuck the shit out of
It was time.
Dave came up behind me. He lifted my arms and put them
on Jon’s shoulders. I was bent at the waist. My face
inches from Jon’s. I felt Dave’s cock push against my
pussy. I had had a hard time getting my lips around the
tip. I could feel its size splitting my pussy. Jon could
see me suck in my breath as Dave entered me.
As Dave buried himself all the way in me I let out an,
“Oh my god.”
Here I was filled with the 3rd and biggest cock I’d ever
felt, being bent over my boyfriend and looking in his
eyes. God it was hot. I was all nerves, every part of me
Dave said, “Ask Jon what he thinks of his slut now.”
I did as I was told. I got into it.
“What do you think? Is this the slut you wanted me to
be? Being fucked from behind by a stranger while looking
in your eyes? Is it turning you on? I hope so, because
it’s really turning me on and I am pretty sure this will
not be the last time you see me fucked.”
Jon grabbed my hair, pulled my face close and kissed me.
Dave kept pounding my pussy from behind. I felt the
start of my first orgasm.
“Oh my god Jon, I’m cumming. Your slutty little
girlfriend is cumming all over a strangers cock.”
The orgasm ripped through me. My knees buckled. David
caught me and carried me to the bed. Jon started to get
Dave looked at him and said, “Stay there.”
Jon sat back down.
To me Dave said, “Get your ass up.”
I didn’t have to be told twice. I got on my knees with
my ass up in the air. Jon was sitting off to the side of
us. Dave climbed on the bed behind me and started
fucking me. Jon told me later he could see Dave’s cock,
covered with my juices, sliding in and out of me.
Dave continued to tell me what a good fuck I was. I
liked it. I wanted to be the best fuck he ever had. I
grunted and moaned with each thrust. It was not long
before I had my second orgasm. Dave felt it and stopped
“Turn around,” Dave said.
I turned. My face was now facing his cock all covered
with my juices.
“Suck it you slut.”
I did. I wanted to make him cum. I wanted it in my
mouth, on my face, on my tits. As I sucked him I
starting begging him to cum.
“Cum for me,” I begged. “Where do you want to cum? In my
mouth? On my face? No ones ever fucked my ass. Do you
want to fuck my ass and cum in it?”
At hearing that Jon’s mouth dropped open. He’d asked me
to try anal, I’d always say no and here I was offering
it to a stranger.”
Dave liked that idea. “Give me that virgin ass,” he
I turned again. This time facing Jon. I put my ass in
the air. Dave got behind me. He started probing my pussy
with his fingers and spreading my juices on my tight
I looked at Jon. “How do you feel now. This guy is going
to fuck my virgin ass before you.”
Jon did not look like he was happy. He looked at me and
shook his head.
He looked a little pitiful. I liked it. I continued.
“Now that I think of it, you can never have my ass. I’m
going to save it for strangers.”
As I said it Dave started probing my ass with his thumb.
“Oh my God Jon, he’s got his thumb in my ass. Do you
think he can feel how tight it is? I can feel him
stretching me out. Getting ready for his cock.”
Dave looked at Jon and said, “Get over here.” He didn’t
ask. He ordered.
Jon did not move. He looked at the ground. He wasn’t
looking at me.
Dave ordered again, “Get your sorry ass over here.”
Jon came up and walked to the bed. Dave told him to
stand where he could see my ass.
“What do you think,” I said to Jon. “Is this what you
wanted? You can watch your girlfriend get her ass tucked
for the first time? An ass you will never fuck.”
Jon didn’t say anything but I could see his cock rock
hard in his pants.
“Pull it out,” I said. “Show us how much you want to see
Dave fuck my ass.”
Jon pulled out his cock. He tried to put it near my
face. He wanted a blow job. I pushed him away.
“Tonight I’m Dave’s slut,” I said. “Get used to it.
You’re going to see me be a slut for lots of men.”
I looked back at Dave. “Do it. Make my ass yours.”
My pussy was so wet the juices he spread on me had my
ass well lubricated. He pushed the head in. I felt my
ass stretching. It hurt, but felt good at the same time.
He stopped and waited for my ass to relax. Jon watche,
stroking his cock as slowly Dave buried his cock in my
“Oh my god Jon. I’ve never felt this full. I’m going to
cum. I’m going to cum with Dave’s cock in my ass. You’ll
never know how that feels.”
Saying that. Feeling Dave’s cock all the way up my ass.
I came. I came hard.
I started screaming. “Fuck my ass. Fuck it hard. Fuck my
virgin ass. Give me your cum. Fill my virgin ass with
I started fucking Dave’s cock with my ass more than he
was fucking me. Jon just watched. I came again. As I did
I screamed telling Jon that Dave’s cock in my ass was
making me cum.
I saw Jon start to spasm. I pushed him away.
“Don’t you dare cum on me. Tonight only Dave gets to cum
where he wants.”
Jon stumbled back. As he did he started to cum. It shot
all over the floor. He got a lot on himself.
I felt Dave start to stiffen. I knew he was about to
“Cum in me. Tonight, only your cum touches me. Fill my
He did. I could feel it squirt in me. As he kept fucking
me I felt some start to drip out my ass.
Dave pulled out of me. I got off the bed. Jon was
sitting on the floor. I straddled him. My ass in his
“See it? Is this what you wanted? Look. There’s another
man’s cum dripping out my ass.”
Jon said nothing. I went back to the bed, took Dave’s
cock in my mouth and started licking and sucking it
clean. I could feel him getting hard again.
The next 6 hours were a blur. A very satisfying blur.
On the way home i had a face covered with cum and
smelled like sex.
“Well Jon, was it like you imagined.”
Jon looked at the road and shook his head no.
I laughed. I laid back in my seat, pulled my dress up,
and started playing with my cum soaked pussy.
As I did, I said to Jon, “I wonder if your friends want
to fuck me.”