I was 25 years old and physically I was in the best shape of my life. I was 5’ 10” tall, I had brown hair, green eyes and I weighed 175 lbs and none of it was fat. The only problem was that financially I was broke just like I had been all of my life. My name is Ray.
I had these two friends that I hung out with since high school Jim and Daniel. Jim was 5’ 9” tall and 165 lbs with blond hair and blue eyes and Daniel was 5’ 6” tall and 145 lbs with red hair and brown eyes. They were just as broke as I was and they were both in good shape physically.
We hung out a lot together on weekends because we could not afford to go out on dates very often.
The three of us stopped at a gas station on the way back from a friend’s party in a neighboring town and I paid for the gas and drinks. The girl that waited on me was very beautiful but she misunderstood me when I was talking to her and gave me a two-dollar lottery ticket to the big jackpot game. I didn’t want to tell her that it was my last two dollars so I took the lottery ticket and left after talking to her a little more. I knew from experience that there was no chance of ever getting a date if she knew that I had no money.
I was taking computer courses online in the evenings after work so I spent a lot of time on the computer. A few weeks after we had gone to the party I noticed a story online about the fact that the gas station that I had visited had sold the winning lottery ticket but no one had claimed it yet.
I checked my ticket and almost passed out when I found out that I was the winner of a huge jackpot!
I told my parents that I had won the lottery and they hugged me and told me congratulations! The next day I went and collected my winnings. The first thing that I did when I returned was I handed my parents a check for a million dollars! I then gave my older sister and my younger brother both checks for two hundred fifty thousand dollars.
I gave Jim and Daniel each a check for fifty thousand dollars and I drove back to the gas station and handed the girl that sold me the winning ticket a check for ten thousand dollars.
Now let’s fast-forward a year.
I was now a certified IT pro with a well paying job and I had a big house in the country on a large lot. My two friends had gone through training and they both had better jobs. We still spent most weekends together but now they were spent at parties at my house. Jim and Daniel each had their own bedrooms and their dates would generally spend the weekend.
On this particular Saturday we had a huge party to celebrate the one-year anniversary of my winning the lottery. We had friends and family over all day starting at 10am. We had the in-ground swimming pool, volleyball, horseshoes, video games, pool, and air hockey and of course lots of food and booze.
Jim and I brought our ladies that we had been dating for a few weeks and Daniel brought his latest bombshell. For some reason Daniel always seemed to get girlfriends that looked like they just walked out of a men’s magazine. Unfortunately his relationships never seemed to last long.
By 10pm everyone else had left the party and it was just my two friends and our three girlfriends.
My girlfriend Jill was 5’ 6” tall with long blond hair and green eyes and she had nice round C cup boobs and a nice round butt. She was very pretty with dark skin and she was a lot of fun.
Jim’s girlfriend Jenny was 5’ 7” tall with brown hair and blue eyes and her boobs were a nice pointed set of B’s with a nice tight butt. She was pretty with pale skin and she talked a lot.
Daniel’s girlfriend Josie was 5’ 8” tall with red hair and green eyes and her boobs were double D’s with a very slim waist and a round butt. She was very pretty, very outgoing and she liked to show off.
Everyone was a bit drunk and we decided to go in the house and relax a bit.
Jenny said, “Why don’t we chill out and play cards?”
Josie replied, “Cards are boring, can’t we play something more fun?”
Jill surprised us all when she said, “Why don’t we play strip blackjack?”
I said, “First let me explain the rules.”
You play in teams and it’s the ladies versus the men. You play blackjack by the usual rules but whoever has the highest hand gets to take one item of clothing off of each member of the opposite team. Once a team no longer has any clothes you get to tell them what to do and they have to do it for a full minute.
We all agreed to play and we all made sure that each of us had 4 items of clothing on. The girls all wore their bathing suits with shirts and shorts over them and the guys wore t-shirts with button down shirts over them and shorts over our bathing suits. Jill found the stopwatch and sat it on the table.
Round 1 was won by Josie and came up to each of us and gave us a French kiss and then took off our shorts.
I won round 2 and I gave each lady a French kiss and then I took off their shirts.
Jenny won round 3 and she gave each of us a French kiss and took off our shirts.
Daniel won round 4 and he French kissed each girl and took off their bathing suit tops. Each of them had gorgeous boobs and very hard nipples.
I was dealt blackjack on round 5 but I noticed the huge smile on Jill’s face when she took another card so I let her win. She winked at me and walked up to Daniel and French kissed him. She then slid down his body making sure to rub his arms and legs with her hard nipples and the she took off his bathing suit. When his bathing suit was off of his feet she slid back up Daniels body and licked his hard cock from balls to tip on the way up. He had an average sized cock.
Jill then moved on to Jim and gave him the same treatment, making sure to rub her nipples on him and licking his cock on the way up. His cock was a little longer than average.
I was the last one to be lucky and she definitely treated me well. When my shorts came down the other girls shouted because my cock is well above average in both length and girth. When Jill came back up she grabbed my balls and sucked my cock into her mouth and went up and down on it a few times before she very slowly let go of it and slid up my body.
Jim won round 6 and he French kissed every girl and on the way down to take off their shorts he kissed both nipples.
I won round 7 and I winked at Jill and walked up to Jenny and French kissed her. I then moved down and spent time at both of her nipples before proceeding to kneel down in front of her. Her bikini was already wet with her juices. I put my mouth on her bikini and breathed hot air right on her pussy and she shivered. I then pulled her bikini down and licked her pussy and she moaned.
I then stood up and moved over to Josie and did the same thing. Josie was very sensitive and when I licked her pussy she came.
When I moved to Jill spent a bit more time on her nipples because I know that they are very sensitive. When I pulled her bikini down I did a butterfly dance on her clit and she came hard.
Daniel won round 8 and he had each of the girls suck his cock for a minute. Jill was first and she started by licking his cock all over. She then sucked his cock into her mouth all the way down to the base. By the time Jim said her 1 minute was up she had almost made Daniel cum. He moved on to Jenny and she was not quite as talented as Jill so he was able to hold back from cumming with her. About 30 seconds into Josie sucking him Daniel could not hold back and he exploded in her mouth. Josie made sure she had gotten every drop and swallowed all of it. As she was swallowing the last bit she stared over at Jill with a smirk on her face as if to say “I won that round”
Jim won round 9 and he also had the girls each suck his cock for 1 minute. Josie was first, Jill was second and Jenny was last. He had to stop and compose himself after Jill and Josie but he was able to hold out without cumming.
Jill won round 10 and she won the right to our last bit of clothing, our t-shirts.
She walked over to Jim and French kissed him while rubbing her body all over him. She then made him sit down and rubbed her very wet pussy lips up and down his cock while very slowly removing his t-shirt. When his shirt was almost off and his arms were in his shirt above his head she rubbed her hard nipples across his chest while still rubbing her pussy up and down his cock. Finally she stopped teasing Jim and they both got up.
As soon as Jim got out of the chair Daniel shouted,
“I’m next” and he jumped into the chair.
Josie gave both Daniel and Jill a dirty look but neither one noticed.
Jill gave Daniel the same treatment as Jim. Josie watched looking a little pissed off and Jennie watched looking very horny and jealous.
It was my turn next and as I looked into Jill’s eyes I could see that she was close to cumming. As she sat on my cock and started to slide I grabbed both of her nipples and squeezed them. She shivered and moaned and moved her hands and her long blond hair out of the way so that I could get to her boobs better. She also started moving faster on my cock. After only about 30 seconds she screamed and came and collapsed in my arms. Once she recovered she kissed me again and then took off my t-shirt.
Jenny won round 11 and she wanted all 3 guys to fuck her. Jenny got up on her hands and knees and proclaimed “fuck me hard from behind”
Daniel was first and while he pumped his cock in and out of Jenny’s pussy Jim and I each played with a nipple. Jill said “time” and we switched off.
While Jim pumped his cock in and out of Jenny Daniel and I moved and each sucked on a nipple. Jim was really giving it to Jenny hard and when time was called she was very close to cumming.
I was last and as soon as my cock was buried completely in Jenny she started cumming. Jenny came the whole minute that I was fucking her and passed out when I pulled out as time was called. Brunette Jenny was done for the night.
The next round was won by Josie and with a wicked look on her face she said “I want all 3 of you at once! Ray; lie down so that I can stuff your cock in my pussy. Daniel; get behind me and lube your cock up and put it up my ass. Finally Jim; come here so that I can suck your cock!”
It took a little bit to get our rhythm going but once it was Josie started cumming nonstop!
Jill sat beside us watching with a glazed look on her face the whole time. She completely forgot about the stopwatch.
After a little bit more time Daniel hollered that he was cumming and he shot loads of cum into Josie’s ass and passed out on the floor. Daniel shooting cum in her ass sent Josie even higher and she started shaking and spit Jims cock out, screamed and then passed out. We laid her down on the floor by Daniel.
Jill said “it’s time for you two to cum in me and make me pass out too!”
I had Jill get on all fours and I stuffed my cock into her already drenched pussy while Jim put his cock in her mouth. We started rocking her back and forth between us so that on the backstroke my cock was buried in her pussy and on the forward stroke Jim’s cock was buried in her throat. She was very close to cumming and when I pushed my thumb into her ass she exploded.
We let her catch her breath for a minute while we changed position. I lay down on the floor and Jill put my cock back into her pussy while facing me. She then told Jim to put his cock in her ass but do it slowly so that she could adjust.
Jill was so hot and relaxed that it didn’t take long before we were in perfect rhythm with Jim and I pretty much holding still and Jill pumping us both in and out of her. Within a short time Jill’s face was flushed and her breath was cumming in gasps.
She then screamed, “Guys you had better cum because I am about to cum and I know I am going to be gone after this one.”
I had her hold still and Jim and I alternated pumping in and out of her. Jim came first, shooting loads of cum into her ass. Jill then came screaming and banging her fists and her pussy clamping down on my cock sent me over the edge also.
Strip blackjack is my favorite game because everyone wins!