Your story site has gotten to be really popular in my college dorm. Some of the girls have agreed to send you stories about their most interesting experiences. Here is my contribution.
I’m a 2nd year coed, 19 years old and I have a fairly active sex life. This story is about getting caught in the act by my sister and her fiance with, get this…her fiance’s brother.
My older sister and I have always been close. She’s 6 years older than me and has always been a role model and my loving friend. Some of my favorite early memories are having her read me to sleep, teaching me to do my hair, sitting on her lap during scary parts of Disney movies. Following her example is the reason I’ve done well in school, stayed away from drugs, and never smoked. But she and I haven’t exactly stayed on the straight and narrow path when it comes to sex.
At 13, I was aware that my sister was sexually active. I used to ask her questions about sex and she answered them honestly. She explained male and female orgasms, showed me how to masturbate, helped me locate my clit, let me compare my vagina to hers, discussed having intercourse and oral sex, and explained about birth control.
When I was 14 1/2 and she was 20, our parents went on a two week combination business trip and 2nd honeymoon. She was supposed to keep me out of trouble. She invited her new boyfriend – Jack – to come over, and later in the evening they went upstairs to her room to make love.
I listened at her door, heard the laughing, soft moaning and creeking mattress springs. I wished there had been a key hole for me to look through.
In the morning, after he had left, I asked her about it. She confessed that he was the most well endowed guy she had ever dated. She had been involved sexually with 28 different guys, and none of them had a penis longer than 7 inches or so. Nature had provided this new boyfriend with a 10 1/2 inch penis. I was fascinated by her story.
She said dealing with his length was only part of the story, his penis was as big around as the pipe from our mother’s Hoover vacuum. She said the first time he penetrated her was a little painful, almost like losing her virginity all over again. But she had gotten used to it after a dozen times or so.
About 3 months later I decided it was time for me to lose my virginity. I let my best girl friend’s big brother deflower me. Without going into detail, I’ll only say it was lots of fun. It also got me into a lot of trouble with my sister. I wasn’t on the pill and the guy didn’t wear a condom. We relied on the early withdrawal method. Right after she finished bawling me out she took me down to the clinic to get on birth control pills and she bought me condoms and spermacide cream for extra insurance.
Getting guys to make love with me wasn’t difficult. I wouldn’t say that I’m beautiful, but I’m desirable enough. On a scale of 1-10, I like to think that I’m at least a 7. I’m blond with pretty green eyes. My forehead is big and I try to hide it with my bangs, but most of my male friends tell met they find me cute and here at college I do get asked out on my share of dates. Bodywise, I’m 5 – 5, 124 lbs, with 35-27-34 measurements. My legs are medium length and nicely shaped. I have the type of body where I can put on weight quickly if I’m not careful, but I run and work out so I’ve stayed relatively slim.
Once I lost my virginity, I made love with a number of my guy friends. I had 6 different partners by the end of my freshman year. I discovered that I enjoy sex without condoms. I enjoy feeling the ejaculation. Knowing that, my sister advised me to avoid sleeping around with guys I didn’t know very well. Luckily I had a number of guy friends who were more than happy to explore sex with me.
That summer my sister’s boyfriend Jack invited her to spend a long week at his family’s ocean side vacation condo at a place called Cannon Beach. This is the same well endowed guy I described earlier. I couldn’t believe it when he told her that I was welcome to come too. I mean, wouldn’t I just get in the way?
I realized later that he really is a nice guy and that he and my sister were really in love. I didn’t know it at the time but he was going to be my future brother in law. The invitation was one of his ways to get to know the members of our family.
His parents were there for the first two days, but they had to leave to attend to their family business. That left me, the two love birds and Jack’s younger brother Thomas. Thomas was 18, and looked a lot like Jack, which meant that he was tall and cute.
Thomas and I got along well. I didn’t think he was attracted to me. When we were down on the beach together, he couldn’t keep his eyes off all the gorgeous bikini clad girls.
Four days after my sister and I arrived, she and Jack decided to go out and have a romantic dinner. Thomas and I stayed behind and ordered pizza. We ate, watched a video then he said he felt like a late night swim. The condo had an indoor pool. I decided to join him.
After swimming about 20 laps we went to sit in the hot tub. I had tried taking a wind surfing lesson earlier that day and the effort had left my shoulders feeling a little stiff. I rolled my head to try to loosen things and he asked me if I wanted my neck and shoulders rubbed. It felt so good. He asked me if I wanted to go upstairs for a full back rub.
Soon I was lying on a towel on the living room floor as he straddled me and ran his hands up and down my back. He knew exactly how to find all the most pleasurable spots. My bikini top was untied. He began massaging my legs, starting with the calves and working his way up to the backs of my thighs. He paid me sort of a complement when he said my upper thighs were cellulite free. I would have liked him to talk about how shapely my thighs and ass were instead. I mean, what was I, chopped liver. Apparently, even if he didn’t say he liked my thighs and ass, he was thinking it. His gentle massaging soon moved up to my full but firm ass cheeks.
I felt the material of my bikini bottoms shifting and I knew he was getting a good view of my pink labia. I was admittedly horny, so I was sure they were swollen.
I asked if he was getting a good view and he said it was more then good, it was magnificent. I rolled over exposing my breasts. Unfortunately, they are not magnificent. They are a smallish A cup size, but they have a nice round shape. My quarter sized nipples were pink and swollen, and the eraser sized tips were pointing up toward the ceiling. He gently cupped my left breast while closing his lips over my right one.
I looked at his boxer style swim trunks and saw a huge bulge. He asked if I was interested in checking out the package. Of course I was. I was treated to an amazing view. His penis was huge, just like his brother’s. Like I said, I had experienced sex with 6 different guys, all of them were average in size.
I told him that my sister had described Jack’s penis as 10 1/2 inches and I wondered if his was the same. Thomas and I measured his and it was 9 3/4 inches long. Not as big but stil impressive. Obviously, big penises run in their family.
He gently slipped the rest of my bikini off of me. My blond pubic hair was still moist and darkened from our swim. He gently toweled it off and blew on it saying he wanted to see if it was the same color as my head.
Then he kissed me for the first time. After some long soulful kisses he said he wanted to see if kissing my other lips was just as nice. The oral sex he performed on me was incredible. He nibbled at my lips, gently pulling them with his lips and flicked my tiny clit with his tongue. I came so good.
I got the whole glans into my mouth, but not much more.
He said I couldn’t possibly be a virgin since I seemed to know what I was doing. He also said that I was too cute and had too nice a body to be untouched by male hands. I admitted that my cherry had been picked 6 months earlier.
He asked if I thought I could handle his penis. When I agreed that I would gladly try, he asked if I was taking birth control.
Soon he was working his huge penis into me. It took effort to get the head inserted into me. I felt very stretched. He was so gentle and patient with me. Obviously he had experience with tight young pussies.
I pushed my hips up to help him enter me deeper. At about 7 inches it hurt, not badly, but it hurt. He sensed that I wasn’t comfortable, so he stopped penetrating. He pulled out a little began using slow, gentle strokes going maybe 6 inches deep each time. Soon my vagina did what vaginas do, it go wetter and longer. He was able to bury it all the way into me and it felt so good.
I had two orgasms before he ejaculated a huge load of cum, followed by another, then another, and again and again. Most guys spurt maybe one huge time, followed by a couple of smaller spurts. He must have released 5 times as much hot cum into me than any guy I had ever been with.
I cupped his ass with my hands to pull him into me so that he wouldn’t try to take it out. We laid there as he carressed my cheek and kissed me. I was in sexual heaven.
Then it happened. We were in the middle of the living room, in full view as my big sis and his big bro walked in. I was on my back, my thighs hugging his hips. They said “Oh my god…” in unison.
They had gotten freshly made ice cream and brought it home to the “kids”.
We weren’t in trouble or anything. If anybody could be cool with the situation it was them.
What happened next was unexpected. My sister said “Well…don’t let us stop you, in fact it looks like fun.” Jack said “Think so…maybe we could do something like that some time”.
They gave each other a “there’s no time like the present look”.
Soon I was watching my sister sucking as much of Jack’s giant penis as she could. She sat on the couch and spead her legs. He entered her with slow, gradual thrusts and I watched in fascination as he worked the massive penis in and out of her beautiful vagina. I always thought hers is prettier than mine. Her lips are thin and delicate. Mine are thicker and not as evenly matched or symmetrical. She also had bigger B cup breasts that are also prettier than mine. I’m a little envious.
Jack looked at us and said “It’s ok for you to have some fun too” and he patted the couch next to my sister.
I obediently sat down, leaned back and spread my legs. My sister looked at Thomas and said “You better be gentle with my baby sister, she has a really tight pussy you know”. I thought it was a little late for that since he had already cum inside of me.
Thomas entered me again and the guys gently thrust in and out of us almost in unison. My sister came after a few minutes, I could tell by the way her body tensed up and by the soft, gently moan she made. We had masturbated togther so I had seen her cum before. I came too, and Jack soon was clearly having a huge orgasm in my sister.
She pulled his face down to hers and whispered something into his ear opposite from Thomas and me.
He said “really” and she smiled and nodded. He smiled and said “OK”.
Then he put his hand on Thomas’s shoulder and said “Time to switch”.
Next thing I knew, Thomas had left me and slipped his penis into my sister.
Jack gently worked his penis into me. His huge penis was filling my little pussy even more than Thomas’s had. I came in one of those long, intense orgasms that made my whole body shudder. My sister did the same a minute or two later. Both guys had huge orgasms soon after my sister and I did.
In an evening of unexpected events, my sister did the really unexpected. After Jack pulled out of me, she knelt between my legs and lapped the mixture of Thomas’s and Jack’s semen as ran from my vagina. I did the same to her. She and I had touched each other’s pussies when she taught me how to masturbate, but was the first time we had ever made oral contact. I continued until she had another orgasm, then she knelt in front of me and helped me get off. I had never has so many orgasms in one night. The guys seemed to like watching us exchanging oral favors, but they didn’t go down on each other. We teased them about their chauvenist homophobic attitudes.
Their idea of eating cream was to polish off the half melted ice cream.
We repeated our foursome three times by the week’s end.
Two years later, my sister and Jack were married. Its hard for all of us to get together at the same time because Thomas goes to school back east. We’ve only done it three times. I have joined Jack and my sister in bed at least a dozen times. My sister and I occassionally have our own love making sessions too. She is still the only girl I have ever been sexual with.
– The End –