Sex Lottery
By: Date: 2022.04.03. Categories: Sex Stories Tags: , , , , , ,

“Ted, I heard you’re having trouble paying your bills.
Is this true?”

What could I say? Kate was the girl of my dreams and I
didn’t want her to think I was a bum. But at the same
time, I didn’t want to lie to her either.

“Oh come on Kate. You know how it is. Water, gas,
electric, mortgage, car, student loans… I’m 24- of
course it’s going to be tight for a while.”

“You don’t have to be embarrassed Ted. I just brought
it up because I thought I could help.”

“Yeah? How’s that?”

“Well, you know my friend Ashley’s dad is so rich that
she will never have to work. Anyway, she has this idea
called a 10 second lottery that she wants to try out.
She has enough participants, but she needs a

“Volunteer for what? And how is this going to help me
with my finances?”

“She hasn’t given me the details, but she said to ask
you if you’re interested. She said that the volunteer
could make up to $20k. So are you interested?”

“$20k?!?! Yeah, definitely interested!”

“Good then meet us tomorrow at 3:00 at her place. You
know where it is, right?”

“8th and Main. 3:00. I’ll be there.”

Famous last words. Let me back up a bit and introduce
myself. I’m Ted. I’m now 25 years old and at the time,
I lived alone. Kate is the girl I’ve had a thing for
since I first saw her 3 years ago. She’s not slutty,
but very sexy. I’m talking long blonde hair, nice ass,
great tits, but always dresses very modern and
professional. She’s a dream. When you give me a
situation that involves her and $20k, I’m there.

I showed up at Ashley’s at 3:00 as directed. I had no
idea what to expect. 10 second lottery? What on earth
could that be? Like Kate said, Ashley was filthy rich.
She had a BMW M3 for spring season, a Caddy XLR
convertible for Summer, a Mercedes for fall, and an
Escalade for Winter. Yeah, she’s that rich. She also is
beautiful, but dresses more slutty than Kate.

Also I guess I should note that I slept with Ashley
once. Typically, Ashley liked to be in control of
relationships and I was no different. I asked her out
on a date about a year ago and she accepted. She said
she’d like to go to a drive in theater, so I took her
to one, we watched the first 5 minutes of the movie
before she leaned over and kissed me.

I, being a guy, was extremely turned on and gave her a
passionate kiss in return. We kissed for a few minutes
until she started fumbling with my belt. She finally
undid my pants and lifted her skirt to reveal that she
had no panties on! Once she pulled my cock out, she
gasped. “Problem?” I asked. “You’re HUGE!” she replied,
turned and began to ride me like there was no tomorrow.

Once I came, she immediately got off me and began
sucking me off until I was hard again. She then got
back on me and rode me some more. This continued until
the end of the movie! When the movie ended, she turned
to me and said “I just wanted to fuck you. I’m not
interested in dating at all. Now take me home.”

Anyway, Kate opened the door before I could get to it
and greeted me with a strong hug. “I’m glad you came!”

“Hey, for $20k how could I turn it down? Plus, even if
it didn’t pay I’d come just for you.” That made her
smile but she didn’t say anything back. I just followed
her inside.

“TED!!” It was Ashley. She came running down to greet
me. “HOW ARE YOU?!”

“I’m fine Ashley. Long time no see. So what’s all this

“Ok Ted, here’s the deal. I had this idea and thought
you’d be the perfect volunteer. The idea is…”

She began to describe her game. There were 20
participants and 1 volunteer. The volunteer (myself)
was to be strapped down to a bed naked. Then, each of
the 20 participants would get 10 seconds to try to make
the volunteer cum. If the volunteer still hadn’t cum by
the time the last participant was finished, they would
start over, only in reverse order. The participant who
makes the volunteer cum would win the pot, which
happened to be $50,000!

“Kate said that there was a way for me to make

“Yes, there is! If you can last longer than 60 fucks
(which if you do the math, that’s 600 seconds = 10
minutes), then you’ll automatically earn $10,000 and
Kate will get a shot at you. If you make it past Kate,
the participants will start over. For each one you make
it past with out cumming, I’ll add another $1,000 until
you’ve earned $20,000. But here’s what Kate didn’t tell
you: If you still haven’t cum by that time, I will get
a shot at you. If I can’t make you cum in 10 seconds,
You’ll get the $50,000 PLUS the $20,000 PLUS you’ll be
able to finish up with whomever you choose, which I
have a hunch will be Kate!”

I was speechless. Was this for real?! My mind was
racing. A possible $70,000 PLUS I’d get to fuck Kate!!

“Ted, are you still with me? Are you in or not?”

“Hell yeah I’m in!”

“Good, then I’ll need you to sign here.” That was the
thing about Ashley. She was rich, but always made sure
she covered herself. “Great… follow me!”

I followed her to a room that was empty except for a
bed and a camcorder. She instructed me to take off my
clothes and lay down on the bed. “Just like I
remembered,” she said, “Huge!” She proceeded to strap
me in until my arms were spread to either corner of the
head of the bed, and my legs were spread to either
corner of the foot of the bed. I couldn’t move at all!
“Oh, and one more thing… You’ll be blindfolded for
the duration of this.” With that, she pulled out a
black leather blindfold and tied it over my eyes.

“OK Kate! Bring in the participants!” I heard the door
open and a bunch of people walk in. “Participant #1
please step up.” I heard someone walk forward and then
sit next to me on the edge of the bed. “Ready… set…

With that, the first participant spit on my cock. I
knew she wasn’t going to win because I wasn’t even
fully erect yet. She started stroking me and playing
with the head of my dick. I must admit, she was quite
good at a hand job! Right as I became erect, I heard
Ashley yell out “TIME! Next participant… Ready, set,
GO!” The next girl had a different tactic. Since I was
already up, she immediately engulfed my penis with her
mouth. It took me off guard. I jerked a little, but
then relaxed and enjoyed the blow job.

“TIME! Next participant! Ready… Set… GO!” Another
blow job. That was followed by another hand job from
the next participant. Over the next 6 participants,
only one used her pussy to try to get me to cum. So far
I had lasted 10 participants and still wasn’t close to

“Next participant, ready… set… GO!” I felt a hand
slip under my back and lift me up a bit. Then a body
slipped under me… a MAN’S BODY! Before I could say
anything I felt his lubed hard cock slide deep in my
had never had sex with a guy and never wanted too.

“Relax Ted,” Ashley replied, “you signed a contract
saying you’d stay until the end of the game and that
you didn’t mind screwing guys. Plus, you’ve already had
3 guys suck you off! Just enjoy it… TIME!”

I was shocked. I didn’t know what to do. The guy
slipped out of my ass and the next participant game
forward. It was another guy, but this time he spread
his own ass cheeks and sat on my cock and began riding


Finally, 20 participants, 7 male, 13 female, had taken
their turn with me and were starting over. The 20th
participant was first this time, and she sat on my
pole, sliding me right inside her pussy. she leaned
forward and gave a deep kiss and started bucking
around, fucking me silly.


The next girl got creative. She had oiled her tits and
started tit-fucking my cock. That felt incredible and
brought me close to coming. I made myself hold off
though because I wanted Kate to have her shot.

The next person was a guy. He tried ass-fucking me
again. It didn’t hurt nearly as bad this time. In fact,
I began to enjoy it. I bucked back, which I think took
him off guard. He started thrusting in my ass harder
and harder. Ashley yelled “TIME!” but he made two more
quick thrusts and came inside my ass. What a feeling! I
never thought I would enjoy getting screwed by a guy,
but I must admit that it was sensational feeling, his
cum slowly sliding out my anus, running down my cheeks
and thighs, and onto the sheets.

Ashley gave the participants a stern warning about
stopping when she called time.

Participant after participant, I was fucked in almost
every way imaginable. A few times I had to really hold
myself from cumming because I wanted Kate. Finally,
Ashley yelled

“TIME! Ted, congratulations! You have lasted longer
than 60 fucks and have earned $10,000 and a fuck with
Kate. Kate, if you can make Ted cum in 10 seconds, the
$50,000 will be yours!”

I heard Kate walk over to me. She reached around my
head and untied the blindfold and ran her hands through
my hair. “I want you to be able to see this one,” she
gently whispered in my ear.

“READY… SET… GO!” Kate lowered her naked body so
that her pussy was wrapped around every inch of my
cock. To my surprise, she didn’t move her hips or
anything. She just leaned forward, softly kissed me on
the lips and whispered “It’s me… Kate… and I love
the way your cock feels deep in my pussy. I love…
you, Ted.”

Did I hear that right?! Did Kate just say she loved me?
Was she just saying that to get me to cum so that she
could win $50,000? I didn’t think so because she had
the look of love in her eyes. She had just brought me
closer to coming than any of the previous 60 fucks had
done. Yet before I could release inside her, I heard
Ashley yell “TIME!” Kate slid off of me, kissed me on
the chest and whispered “Hold out for me. I’ll make it
worth it.”

I did. I held off for the next 10 participants, earning
myself $20,000. During those participants, two more
guys came in my ass (they had been stroking their cocks
before hand), which nearly pushed me over the edge, but
I held off for Kate.

Next it was Ashley’s turn. Ashley stripped her clothes
and handed Kate the watch. She walked toward the bed,
but stopped just before it, bending down to pull
something out from under the bed. It was a vibrating
dildo! She flipped the switch making the 10″ thing hum,
lubed it up and shoved it hard in my ass. Then she sat
on my cock, and went wild. I’ve never experienced such
a fuck! Her hips moved so fast, side to side, back and
forth, up and down.

She could feel the vibrations from the dildo in my ass
and it sent her into immediate orgasm. She shuddered as
she came on my cock. I couldn’t hold back any longer,
even if I did get to fuck Kate next. I had to release.
But just before I let myself go, I heard Kate yell
“TIME! That’s it! He did it!”

But Ashley was powerless in her orgasm. She couldn’t
get off of me. She moved up and down three more times
and I thrust myself deep inside her. I could feel the
head of my cock reach her womb as I let go and shot
stream after stream of cum deep into her womb.

“OH GOD!!” she cried.

“NO! NOT FAIR! I YELLED TIME!” yelled Kate. I looked at
her and saw tears running down her face. “I CALLED
She was getting hysterical. Ashley just ignored her as
my cum continued to fill her cunt. “HE WAS MINE! I

Kate was crying hard now. She ran over and grabbed
Ashley by the shoulders and tried to pull her off.
Ashley pushed her back. “Relax Kate! I know you called
time. The $50,000 belongs to Ted. I couldn’t get off of
him. I’m sorry. I’ll get him back up for you and you
can fuck him all you want.”

“NO! BACK AWAY FROM HIM!” Kate pulled her more
aggressively now, pulling Ashley to the floor. She took
my cock in her hand and licked it like a popsicle
before wrapping her whole mouth around me. It didn’t
take me long to get back up (after all, this was only
the first time I had come). Once I was hard again, she
got up and sat on my cock, putting her hands on my
chest. She rocked back and forth, lowering herself on
to me each time, slowly at first, but gaining speed
with each movement. Finally, I was all the way inside
of her, touching her womb also.

“OOOOOOH!” she moaned. She continued rocking on my cock
while I looked over and saw Ashley writing in her
checkbook, cum leaking out of her snatch. This sent me
over the edge and I pushed as deep as I could into Kate
and came again. I had just cum inside the girl of my
dreams, with someone else’s cum drying in my ass, while
another girl was writing me a check for $70,000 with
cum, my cum, seeping from her pussy. Amazing! Then, to
top it off, Kate looked in my eyes and said “I really
do love you. I always have.”

Two weeks later, Kate and I were at her place lounging
on the couch watching TV. She was only wearing one of
my tee shirts as we had just finished having amazing
sex. She stood in front of the TV and said “Ted, we
need to talk.” I could tell this was going to be one of
those serious talks, so I turned the TV off.

“What’s up, Kate?”

“Do you love me?”

“Yes, baby, of course I do. You know that. Why?”

“I’m pregnant. I found out last night. You’re the only
guy that’s fucked me in over 5 months, Ted. I’m having
you’re baby.”

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