Fun with Dianne
Introduction:
Dianne loved to fuck and older men were her favorite partners
Diane was 5’1″ tall and only weighed 102 pounds.  Her tits were shaped 
like someone had cut a medium sized navel orange in half and put the 
two halves on her chest.  She had large dark nipples that showed very 
sexily in the clothes that she wore and got hard as soon as she started 
to get turned on. Her skin was the color of milk chocolate and she kept her 
black hair straight and shoulder lenght. She could easily pass for a high 
school girl rather than the 22 that she was and she was almost always carded 
when she went to a bar, if they did not know her.   Dianna was one cute little lady 
with a wicked smile that almost told a guy that she wanted to be fucked. 
Diane didn’t like guys her own age.  She much preferred men in their 30’s, 
40’s and even 50’s.  They were more mature, experienced, enjoyed more 
playing rather than just a quick fuck to get their own pleasure, and usually had 
more income to treat her to some fun times.  And she also did not like just one 
at a time.  These older men were usually so happy that a young girl wanted to be 
with them that they made every effort to make sure that she enjoyed their encounter.  
She was not a prostitute.  She just liked sex – lots of sex.   One of Diane’s favorite 
ways to get picked up was to go to the bars near the convention center when a 
convention was in town and all the businessmen were in town away from their 
wives and sweethearts.  She would pick out a table or booth with three or four guys 
at it and walk up and ask, “Hi Guys, would you like to buy a little girl a drink?”  She 
was hardly ever turned down. 
 Diane had two types of outfits that she liked to wear when she went out 
for an evening of fun and both of them worked very well for her.  The 
first one played on her young looks.  It would consist of a mid-thigh 
pleated plaid skirt and a white button front blouse with saddle shoes and 
white socks.  Yes, the schoolgirl look.  The other was the slut look.  
She had tight skirts that came just below her ass cheeks and lacey see 
through blouses with very open necklines, mesh stockings and spike healed 
shoes.  Of course, with these outfits she did not wear any underwear and 
wore heavy, dark red lipstick.  The way her tits were shaped she sure did 
not need a bra.  They did not sag at all and the nipples pointed straight 
forward. Like I said,  both outfits worked, but she could tell the difference in 
how the men treated her depending on which outfit she was wearing that 
night. 
 It was a warm spring night in L.A. and Diane decided that she would go 
out in her schoolgirl outfit that night.  There was a convention at the 
Long Beach Convention Center that week.  It was Friday night and the guys 
had been in town for about three days now so Diane knew that there would 
be a lot of horny guys in the local bars that night.  As she stood in front 
of her mirror putting on her outfit, she could not help but admire how 
tight her body was.  Her firm tits and her flat stomach were something to 
be admired and she wanted to find some men to admire her that night.  Diane 
could not help but let her hand rub her tits and pinch her nipples and then 
it went down across her stomach to her pussy, which she kept neatly trimmed 
for when she wore a bikini.  As she spread her legs and her finger slipped 
between her pussy lips she could feel that she was already wet from 
anticipation.  She let her finger slip up into her cunt and she finger 
fucked herself for just a minute then took her finger out and rolled her 
large clit between her thumb and forefinger.  Shortly she felt herself 
approaching an orgasm but she wanted to save that for later that evening 
when she was in the company of horny men to do it for her.   She reached a 
tissue from the box on the dresser and wiped the pussy juice that she had 
released because of getting herself turned on and thinking about what was 
about to happen, and she knew that she could make it happen.  She put on 
her red silk panties and the rest of her schoolgirl outfit, brushed her 
hair, turned her bedroom light out and headed out the door to her car. 
 As she entered Danny’s – an upscale restaurant and bar overlooking the 
marina – at about 10 o’clock, she looked over the crowd that was there 
that night.  She did not know the bouncer who was on duty that night so, 
as she expected, he asked her for her ID.  Especially in that outfit, she 
could not have expected him to have any idea that she was of legal age.  
There were several couples and several single men and other groups of 
men about her age.  She saw a couple groups of men that might be of 
interest.  After looking each of them over for a minute she picked the 
group that seemed to be just what she was looking for.  They were three 
white men sitting in a booth at the window overlooking the marina.  The 
two on one side looked to be in their mid to late 30’s.  The other appeared 
to be in his early 50’s with graying hair.  They were all fairly attractive and 
all dressed in dark gray suits with white shirts and bright ties, although 
the ties were loosened.  They all had mixed drinks.  For some reason 
Dianna found that she had a better time with men who drank mixed drinks 
when she has wearing her schoolgirl outfits and more fun with men who were 
drinking beer when she wore her slut outfits. 
She walked over to the booth and with a shy little look she said, “HI Guys,
would you like to buy a little girl a drink?”   As she expected the older 
man said “sure thing little lady” and the other two nodded their heads yes.  
Diane slid in next to the older man and said “I’ll have a bloody mary but my 
name is not Mary.”  The older man said that his name was Paul and that the 
others were Dave and Rick.  “I’m Diane.  I haven’t seen you in here before.”  
“No, said Paul, we are in town for the convention.”  Paul started to look a little 
worried and asked Diane how old she was.  She replied that she was 22 and 
had been carded when she came in but she would prove it if he wanted.  “Oh no, 
that’s ok” Paul said and relaxed.  They talked small talk for a little while about
 the weather and California and had a couple drinks at which point Diane said, 
“Do you have someplace a little more private where we can continue this 
conversation?” and she reached down and gave Paul’s cock and balls a gentle 
squeeze.  “You bet I do.  Let’s get out of here.”  Diane slid out of the booth and 
Paul quickly followed her.  Dave and Rick sat there till Diane said, “You guys 
are coming too aren’t you ?”  Their eyes brightened and they looked at Paul 
who nodded his head yes.  It was hard to believe how fast they got out of the 
booth. 
 They were staying at the hotel just about a two-minute walk from Danny’s so they 
walked.  Dave and Rick had a room that they shared on the forth floor and because 
Paul was the boss he had a room on the tenth floor overlooking the water.  As they 
walked into the room Paul put his hand on Diane’s ass and she giggled.  The room 
was large and plush with a king sized bed.  Diane turned and looked at the men and 
said “I bet you have guessed it already but I want the three of you to fuck me tonight.”  
There was no question about who was expecting to be first but Dave and Rick started 
to confer about who would be second.  Then Diane said “No, no guys, I want you all to 
fuck me at the same time and we are going to do it the way I have planned.  Now, the 
three of you handsome hunks take your clothes off.”  She was being nice because 
they were not all that handsome.   
 All three took off their cloths and Diane told them to stand side by side.  She sat on 
the side of the bed and told them to stroke their cocks while she got undressed.  She 
turned on the radio and danced a sexy strip tease as she got out of her clothes.  While 
she was dancing she was looking at the men.  Paul was about 6′ with a little bit of a 
middle-aged belly.  His cock was about 6 1/2″ and pretty big around.  Rick was about 
6′ 2″ and nice and slim.  His cock was probably a little over 7″ and very thin.  Dave 
was about 5’10” and chubby.  His cock was less than 6″ but the thickest of the bunch.  
When she had finished taking off the last of her clothes she stood in front of the three 
very happy white men and just wiggled her perfect milk chocolate body about for them to 
enjoy looking at and then she went up to them and got down on her knees with their now 
hard cocks pointing right at her mouth.  “Ok guys, hands to your sides” and she started 
sucking them in rotation. 
 Diane was proud of the fact that she was an expert cocksucker.  When she was 14, 
her 18-year-old brother had come into her room and forced her to suck his cock.  His 
cock was, as she learned after seeing many more, big at over 8″ and so big around that 
she could not get her hand all the way around it.  Every time he held her head and 
pushed in and touched the back of her mouth she started to gag and when he shot into 
her mouth she did not know how to shallow it and she coughed and gagged and spit 
most of out of her mouth and all over her face.  But before he was done with her she found 
that she was enjoying the thrill and feeling of it.  When he came to her again the next night 
she was a willing participant and within a couple weeks of sucking him almost every night 
she had learned to deep throat his black monster and swallow every drop.  It was a couple 
weeks later that she was the one who approached her younger 12-year-old brother and 
took him to her room.  She was surprised that he turned out to be only about 5″ and thin 
with no pubic hair but she enjoyed sucking him anyway.  When he started to come he 
jerked his cock out of her mouth and she saw him shoot a large load of thin cum almost 
two feet.  She thought that was neat and quickly learned to aim it so his cum landed on his 
own face.  But then she would lick his face clean.  Diane would not let her brothers fuck her, 
but she enjoyed sucking them any chance she got.   
 Just after her 15th birthday her father, who had only lived with them off and on for as long 
as she could remember, caught her and her older brother and grabbed her by the wrist 
and dragged her to his room swearing at her for being a slut that needed to be punished.  
He sat on his bed and pulled her shorts and panties down and pulled her over his lap and 
started spanking her and continuing to swear at her.  Her ass got bright red and almost 
numb. Soon he got sexually excited and it turned into a rape.  He shoved into her taking 
her cherry and filling her pussy with cum for the first time.  He had left the door open and 
she could see both of her brothers watching her get raped.  He moved out again the next 
day.  
After that she found herself fucking and sucking both of her brothers and just about 
every guy that showed any interest.  She did it with men as old as 60 and sucked boys as 
young as 10.  The first time she was fucked in the ass was when she was on top of her 
older brother fucking with him and her 35 year old uncle who was visiting heard the noise 
they were making and came into the room.  He quickly stripped off his clothes and got on 
the bed behind her.  He spit on his cock and on her ass and shoved his 7″ into her ass hole.  
It hurt like hell and she screamed and tried to get away without any luck.  By his second 
shove he was fully buried in her rectum and pumping his cock into her bowels.  Gradually 
the pain went away and she realized that she would be adding ass fucking to her fun in the 
future.  The two men came at about the same time.  Her uncle grabbed her by the hair and 
forced her to suck them both clean.  She did not like the taste of his shit covered cock but 
knew that this would not be the last time a man would want her to do this. 
 Now Diane concentrated on the three cocks in front of her.  She told Paul to get on the bed 
on his back and she got on and first startled his face and had him lick her wet pussy.  Then 
she moved over his hips and lowered her pussy onto his shaft.  Next she reached into her 
purse and gave Rick a small tube of KY Jelly.  He got on the bed and rubbed a liberal amount 
onto his cock and pushed it into her.  By now she knew how to relax her often used back hole 
and he went in with ease and no pain.  They both started pushing into her and pleasuring 
her holes.  She motioned to Dave to come to her and told him that she wanted him to fuck 
her throat.  Dave got on the bed on his knees in front of her, put his hands behind her head 
and slammed his cock deep into her throat with one push.  She was ready for it and took it 
with no trouble.  All three men fucked her fast and hard and deep.  Paul came first after about 
two or three minutes and filled her pussy with his cum.  Dave lasted a little longer.  Diane 
could tell when he was about ready and she stopped him with his only his cock head in her 
mouth because she enjoyed having her mouth filled with cum rather than having the guy 
shoot down her throat.  Rick, he was like the energizer bunny.  He just kept going and going 
and going.  He must have fucked her ass for twenty minutes.  She had two orgasms of her 
own while he did.  Paul and Dave watched for a while till they were both ready for more and 
came back to come in her mouth again.  Finally Rick sprayed her bowels with his cum and 
they all lay on the bed worn out.  
Diane got up and started to dress.  Paul looked at her and asked, “That was fantastic Honey.  
How much do we owe you?”  “Nothing.  I’m not a prostitute.  You guys were great.  Thanks.”  
Paul said “I have some big customers that I am sure would like to spend some time with you 
and me.  I have a yacht chartered for tomorrow to entertain them and a chef hired to cook us 
a feast.  Would you like to join us?”  “Sounds great to me.  What time and what slip ?” asked 
Diane.  Paul told her and she kissed each of them goodnight and headed home to rest and 
get ready for the next night. 
605.
 
   
                        