A few years ago, my dad became rich. He was an early employee with a computer tech company and when they went public his stock options were worth over $8 million. He and my mom used some of that money to buy a nice condo in Hawaii. They were in love with the islands because they met there as college students and then honeymooned there. The idea of owning a luxury condo was a dream come true.
I was 18 the first year we went to spend an extended summer vacation there. By that age I looked good in a bikini. I haven’t changed much in the 4 years since.
I’m a very pretty brunette. I’m told I look like Holly Marie Coombs, that cute actress who plays Piper on Charmed. I’d have to agree. I’m 5 foot 2, and I weigh a well toned 110 lbs. My boobs aren’t big – they are only B cup sized – but every guy who has seen them has been impressed. They are firm, have a nice round fullness, and my perky pink nipples and quarter sized areolas are a succulent pink. My other measurements are 24 and 32 so I am well curved. I wish I had longer legs – I only have a 30 inch inseam – but they are smooth and nicely muscled and shaped. I know guys enjoy seeing me wearing shorts or mini skirts.
So that first summer at our new condo gave me a chance to really show off my hot young body. I loved putting on a bikini and strutting down the beach. I admit that I’m a horn dog. I have been since I lost my cherry when I was 14, but more about that later.
A few days after we arrived in Hawaii, I met some locals. I was watching them surf and they noticed me watching and they waved me over to them. We made small talk and I explained that I was living in the condo a quarter mile down the beach.
They were mixed blood meaning not pure Hawaiian. They were part Hawaiian, part Asian (Chinese, Japanese, maybe some Filipino, they weren’t totally sure) and part white. It didn’t matter what they were, they were cute. There were 5 of them in this group and they were all related. Louie , Manny, and Donnie were brothers. They were 21, 19 and 18 in that order. The other two guys were their cousins, Yuki was 19 and his brother Sonny was 18.
They asked me if I wanted to learn to surf and I quickly agreed. I spent about an hour getting my first surfing lesson. Two of the guys, Louie and Yuki were actually surfing instructors who competed in local meets. They worked out of a surfer shop called the Hang Ten. But they didn’t charge me for lessons. But I wound up thanking them in a way that was much better than money.
For that first afternoon, they were just nice gentlemen giving the “Howlie” girl some island hospitality. It probably helped that I’m a pretty girl with a nice body. I don’t think they would have given a fat white guy the same treatment. Even so, they didn’t make a pass at me.
Like I said, I was already indoctrinated to the joys of sex. I had lost my cherry 8 month’s earlier and had let 11 guys fuck me since that time. I found myself thinking about which one of these guys I would like to fuck the most. I masturbated that night thinking about their muscular tan bodies, and it just sort of dawned on me that I could fuck all of them. I was going to be in Hawaii for the next three weeks, that was plenty of time to go out on 5 dates.
It hadn’t occurred to me that I might fuck all of them at once.
Day two was like day one. They were gentlemen and I was more than a little disappointed that they hadn’t at least made a racy remark or two. The third day I me Dawn, a beautiful 18 year old girl who was Louie and Yuki’s sister.
She was the epitome of a Polynesian beauty, long luxurious black hair, smooth brown skin, a figure and legs to die for. We became fast friends and toward the end of the day she said “Well now I know why all the guys are so smitten with you.”
“Really” I replied “I had no idea, they treat me like their sister.”
She laughed and said “Take my word for it, they don’t look at you like a sister.” She walked me home and met my parents. My brother Mark, who was 17 was obviously smitten with her, and I got the impression she might have feelings for my big bro. When we were alone she asked if Mark had a girl friend. As luck would have it, he had just been dumped a few weeks earlier. I told Dawn that if she offered to show him around it would raise his spirits. She asked me to put in a good word for her and I said I would if she would do the same for me. I said “I don’t care, any of them…all of them”. Her eyes widened and she said she didn’t want the guys fighting over me, so maybe I should make a date with each of them. Little did she know that was exactly what I had in mind. After she hugged me goodbye, I went to tell Mark she was attracted to him. It definitely lifted his spirits.
The next day Mark and I went down to the Hang Ten shop so that he could get another free surfing lesson and so that he could see Dawn.
I had put on a really revealing bikini that day, it was basically a thong with a tiny top that exposed the sides and most of the upper part of my breasts. My areolas were only about an 1/8 of an inch of material from being exposed. My parents hadn’t seen it because I had on a T-shirt and a wraparound when we left. I took both off and put them in my bag as we got close to the shop. Mark rolled his eyes and said “Better not let mom and dad see you like that.”
When we got to the shop, Dawn was dressed in a bikini nearly as skimpy as mine. She was obviously trying to impress Mark.
We all spent the day together, but I sensed that the guys were viewing me a little differently. Dawn had told them how cute I thought they all were so I think they were considering the possibilities of taking me out and where it might lead. They didn’t make any moves, not with my brother there, and of course he didn’t put any moves on Dawn. As it got later into the afternoon, Louie said “Hey, you two should come over tonight for a back yard barbeque”.
Mark and I agreed, and called home to let the folks know where we were. The food was great. I was in the same skimpy bikini and wrap around. Dawn had changed to a floral bikini top with a short matching wrap around skirt that showed off her smooth brown legs, with a beautiful red flower in her hair. I giggled when I noticed Mark trying to hide his erection. I know for a fact that my brother is big if you know what I mean. I’ve talked to a couple of girls who have gone to bed with him and his organ is nearly 9 inches long. I know there are guys who are much bigger somewhere in the world, but I’d never been with one of them. After a few minutes his excitement had ebbed but I quietly teased him several times about trying to keep his penis down. He told me to shut up.
Anyway, dinner was served and we ate pork ribs, this incredible fish, and I even tried poi. Then Dawn offered to take Mark for a sightseeing drive. I whispered to him just before he left “Be gentle with her”. He gave me a dirty look.
So there I was, in the back yard on a warm romantic night with 5 cute, hard bodied guys. There was some traditional Hawaiian music playing so I got up and said “So who’s gonna teach me to do the hula”.
Donnie volunteered, but instead of showing me the moves with all the hand movements, he showed me how to do a dance with rapid hip movements to keep time with a fast drum beat. I tried and did pretty well. Then Manny brought out a straw skirt and told me to put it on. I took off wrap around making sure that they all got to see my lovely ass. Then I put the skirt on and tried to do the dance again. The skirt fell off and I laughed and asked how they kept them on in the old days. Louie said its a good thing that in the old days the women only wore the skirt. They didn’t wear tops and they didn’t wear panties. Yuki said “You really should try to dance the old fashioned way”. I know he was joking and really didn’t expect me to take off my top or drop my briefs, but I said “Well, if you think I should.”
I took off my top and proudly showed off my firm white breasts. Then I reached under the grass skirt and slid my bottoms down. They guys grinned in disbelief. I then started the rapid hip shaking and I felt my firm breast jiggle. The skirt fell off again and there I was completely naked.
I don’t shave but keep my pubic hair neatly trimmed and I felt their eyes lock onto my young crotch.
Soon I was inside the house with 5 naked guys. They all had erections, all about 6 inches long. I moved from one guy to another, sucking on the hard brown stalks.
Manny was the oldest so he got to fuck me first. I was lying on my back on a big soft couch with my legs spread. Manny got on top of me and gently put his dick in. I’m small down there and he loved how tight I was. He said “Oh man oh man, she’s tight as a clam”. I’d never heard that before but I took it as an island compliment.
He started to fuck me hard but like I said, I’m small down there and it hurt. I gasped and asked him to take it easy until my pussy got a little better lubricated. He obliged and I really started to enjoy it. He fucked me to two orgasms before he came. I like it when a guy ejaculates in me. The feeling of cum hitting the walls of my cunt is a nice sensation. Yuki was the next oldest so he go to go second. They each fucked me in order of age. Every one of them was gentle and gave me a nice hot shot of cum.
Sonny was the youngest so he went last. I could tell he wasn’t very experienced because he didn’t have that much control. He came in less than 2 minutes.
What was so fun was having sex while being observed. As I said, I like showing my body off and fucking in front of a crowd is the ultimate act of showing off.
Yuki waited for Sonny to finish cumming in me, then he positioned me on my hands and knees and fucked me doggie style. I don’t know when it happened but a couple of other guys showed up. Both were big heavy set natives. They looked like the big Samoan football players at my school. Both saw what was going on and they knew they wanted to join the gang bang.
One had an average sized dick, but the other was big. His penis was close to 9 inches long, maybe more, and so thick.
I couldn’t believe how much it stretched and filled me. It hurt, not really bad, but it hurt. I couldn’t take all of it. He used about 6 or 7 inches to fuck me until he needed to cum, then he pushed it all the way in and filled my cunt with yet another load of cum. The gang bang began about 8 o clock and by 9:30 I was all fucked out. I couldn’t move my hips or squeezed my vaginal muscles anymore. Those 7 guys must have cum in me at least 18 or 19 times.
I went into the bathroom to shower and let most of the cum drain out of me.
Dawn and Mark returned about 10:30, and Dawn drove us home.
Once we were home I asked Mark if he had been “romantic” with Dawn and he grinned. “You and she did the…you know”. He said “God Jenny, it was fantastic”.
I told him I had some fun of my own. I told him I had my first gang bang. He looked at me in disbelief. He said “Geez Jen, I knew you let guys, but I didn’t know you were that into it”. He described how wonderful Dawn is. She, according to Mark was incredibly soft and tight inside. I asked if she was able take it all. He said she was used to be dicks because one of her brother’s friend’s was well hung. I told him I had met and fucked the guy. I then went into detail. I had never been so open with Mark. He knew I was sexually active, but we had never talked about it.
I asked if Dawn mentioned if his penis was as big or bigger than the big dicked islander’s. She mentioned that they were about the same size. I wanted to see if she was right so I just sort of blurted out “show me”. To my surprise, he did. It was about the same size as my earlier partner’s, but instead of being brown it was covered by very fair skin. But the head was big and purple like my island partner’s. I slipped my bikini briefs off and masturbated while letting him admire my tiny pussy as we shared details. We didn’t do anything sexual to each other, I just admired his dick as we continued to discuss our evenings. I wasn’t sore at all from all the fucking. He stroked his dick and ejaculated in front of me, and I had a nice orgasm of my own. I chuckled and said “Well, I guess I should say good night”. I kissed him on the cheek and thanked him for going to the barbeque with me. He thanked me for introducing him to Dawn. That was the only time we ever shared so intimate a time together.
I had 3 more gang bangs before we returned to the mainland. The last time was with 11 guys. Even though I wanted to I didn’t take part in any gang bangs at home. I’m sure I could have gotten a lot of guys to gang bang a cutie like me, but I didn’t want to be known as the school’s biggest slut. It’s one thing to have a sex life, but being known as the school tramp is not a good thing.
I have enjoyed gang bangs with my friends every time I’ve gone back to Hawaii.
– The End –