I’m a 2nd year coed and I love to surf erotica sites as a way of relaxing between study sessions. A friend turned me on to your story site, and I just read a story called “2 plus 2”. As I read it, all kinds of memories came rushing back. The writer’s experience was similar to my own, and I too have been carrying around some guilt about it. The sexual encounters I’m going to describe happened a little over years ago.
I admit that I am a very sexual person, in fact some people would say I’m over sexed. For me, sex isn’t just about having orgasms. The attention I get from guys and the knowledge that guys find me so desirable gives me a rush. I know I possess a relatively high IQ, but I’d rather be admired for my looks than my brains. I’m not sure what that says about my self image or confidence, but I like the idea that I’m so desirable to men.
So here is my story.
My brother is two years older than I. He spent his junior year in France on an exchange program. When he left, I was skinny and barely starting to develop. Just after I said goodbye to him, the hormones that control growth and development kicked in and I grew from 5 -1 to 5-5 in just 6 months. I turned into a pretty, hazel eyed blond. My dimensions are 34B, 24, 33 so I have nice curves. My breasts are only medium, B-cup – sized but they are very pretty, with quarter sized areolas and classic pencil eraser sized nipples that really pop out when I’m aroused. My best features are my long shapely legs and my ass. I can honestly say that within a year of the time my brother left, I was truly one of the more desirable girls in my class. I became sexually active too.
I surrendered my virginity just a month before the end of my freshman year. I loved it. The guy was a popular senior who I know had more than his share of sexual playmates over the years. From the things he said and the way he acted, you would have thought I was the Playmate of the Year. He told me I have the nicest legs of any freshman. Once we started fucking he also told me he couldn’t get enough of my tight soft pussy. Even after he had come in me 3 times, he just wanted to keep his semi-erect penis inside of me. Of course he bragged to his friends and I soon had dozens of older guys asking me out. I loved that I had my pick of the hottest guys in school, and I had sex with 11 different guys in the remaining month of that school year. That earned me a reputation as a nymphomaniac, and the thing is, I didn’t care. I liked being considered one of the hottest girls in school.
My brother came home a couple months after I lost my cherry. It was late summer and he was surprised by how much I had changed. Our neighbors let us and our friends use their pool during the summers. They kind of appreciated us making noise during the day to keep potential burglars away. The day after my brother got home, we went for a swim and when he saw me in my bikini, I know he was surprised by how my body had developed. His two best friends, Jake and Sam showed up to spend some time with my brother. Like my brother, they were seniors to be, and I’m sure they were plugged into the school grapevine so they were well aware of my sexual antics.
I could feel their eyes following my bikini clad form. They were both cute and truth be known, I wouldn’t have minded dating either of them, but they had never made a move. Both were friendly when I saw them around school, and sometimes they would give me a lift home, but neither made any moves on me. Like I said, they must have been aware of my recent deflowering. I attributed the fact that neither had invited me out to my brother. There must have been some code that best friends don’t fuck one another’s sisters.
A couple days after my brother came home I ran into Sam’s sister Nicole. She is a year older than I, and she is incredibly beautiful. Think about the actress Eva Longoria to get an idea of how beautiful she is. She and I weren’t close friends but we were friendly. She asked how I liked having my brother home. I told her I was happy to have him back and she made an interesting comment. She said “I know more than a few girls who will be happy to have him back.” He’s kind of cute but I didn’t think he was exactly the hottest guy in school. I said “Really, I don’t think he’s all that hot….I mean, he’s just OK isn’t he?” Nicole laughed and said “He’s cute, but its that other quality that sets him apart.” As she said it she held her hands up to indicate something about a foot long. I knew what she meant and I was shocked. My brother?
Nicole informed me that she had a date with him that evening. My imagination ran wild with what they would be doing.
I went out too, with a couple of my long time guy friends. I told my parents we were going to play miniature golf. We did start out for the amusement park but the guys were distracted by the fact that I was wearing a very short pair of shorts and a cute top that showed a lot of tummy. We decided to have some recreational sex instead. It was the first time I let either of them, and only the second time I was ever involved with more than one guy at a time.
The first guy of the two guys to penetrate me was very average in size, about 5 inches. The second was big, at least for that time in my young sex life. Taking his 7 inch dick into me was a tad bit uncomfortable and I found myself wondering how Nicole was going to take my brother’s foot long penis into her. I mean, she was 2 inches shorter than me so her pussy couldn’t be any deeper than mine.
After we both got home, we were having a snack in the kitchen. I wanted so badly to ask him about his date but I didn’t know how. He must have sensed that I wanted to talk so he said he heard that Nicole and I had a talk earlier that day. I felt myself blushing but I asked him if what Nicole told me was true and I held up my hands like she had. He looked a little embarrassed, but he said it was probably half true, his penis was more like 9 inches rather than a foot long. He also told me he had heard that I had become sexually active. It was my turn to look uncomfortable, but he said it wasn’t his place to judge me. He kissed me on the forehead and went to his room. Despite the fact that I had just had sex, I masturbated myself to sleep wondering about what a 9 inch penis would be like.
The next day, after our parents had gone to work, I answered the door and was surprised to see Nicole standing there.. She was looking so cute dressed in a sexy pair of khaki shorts and a cute top with a open denim vest over a bikini top. My brother yelled from the kitchen for me to bring her in. I’m not bi, but I enjoyed seeing her long sexy legs and perfect ass as she walked away from me toward the kitchen. She had come over for a mid morning swim. As they left for our neighbor’s pool, she looked at me and asked “Aren’t you coming with?” I didn’t want to get in the way but my brother waved his arm to get me to follow.
Nicole is so pretty and seeing her in a almost thong style bikini was a treat for anybody’s eyes. She is a cheerleader and my guy friends would almost cream in their pants when she jumped around in her short skirt and sexy sleeveless, bare mid-drift top. She looked at me in my bikini and said “Don’t you look cute”. I liked hearing that from one of the most beautiful girls in school.
After a while, they told me they were going upstairs and it was clear what they meant. I wanted so badly to be a fly on the wall. To this day, I still have a hard time believing what I decided to do. My brother’s room is on the back side of the house. The roof over the back porch extends all the way across. If I crawled out of my parent’s widow and crept across, I might be able to peek into his window. I quietly made my way across and was happy to find a tiny gap under his window blind. I peeked in just on time to see her drop her top and expose her magnificent C cup sized breasts. They were so perfect in size and form. The snowy whiteness of her breasts was such a sexy contrast to her light brown tanned torso, and they were tipped with beautiful brownish pink nipples surrounded by slightly darker, nickel sized circles. My brother slipped her bikini panties down and I was able to admire the most perfectly formed vagina. She was lying on her back, just 6 or 7 feet away and I could clearly see the beautifully symmetrical, delicate brown lips. Her opening looked so small, how was she going to let a guy with a 9 inch penis enter her?
My brother dropped his trunks and he was already full erect and I felt my heart pounding. It was so spectacular, not just because of its size, it was so perfectly shaped. It looked massive against her sweet, pretty face. She took the head and maybe an additional inch into her tiny mouth. I wanted to change places with her. After just a minute or so, I watched as my brother’s balls contracted and the base of his penis stem seemed to flex and I knew he was pumping her mouth full of semen. Then he went down on her beautiful pussy, and I wanted to trade places with him. She arched her back and shuddered as she came. Then the thing I was waiting to see happened. He entered her. From my position, I could clearly see the big purple head gently work its way between the tiny lips. She thrust her hips up to help him move deeper into her. It was obvious she was having pleasure, not pain. I think I saw her flinch a few times as he got deeper into her but she let him continue. He smooth, beautiful thighs framed his firm ass as he thrust in and out of her. I couldn’t watch any more and I crept back to my parents room and hurried to my room to masturbate.
After an intense orgasm, I got dressed and ran out of the house. I didn’t want to look them in the eye after spying on them What would I do if they found out?
I headed for the park where my friends often hung out thinking I might get one or more of my guy friends to give my incredibly wet vagina a work out. A horn honked and Nicole’s brother Sam pulled up. He asked if Nikki was still at my house. I asked “You know she’s there?” He told me he was the one who dropped Nicole off. I asked if he knew what they were doing. He said “If they’re done swimming they’re probably making love”. I must have looked shocked because he asked “Are you upset about it?” I told him I thought there was some sort of rule about guys not fooling around with a friend’s sister. He told me he wasn’t aware of any rules like that. In fact he told me that Jake had hooked up with Nicole several times, and both Sam and my brother had hooked up with Jake’s beautiful sister Ashley. Ashley was the same age as Nicole, and a very beautiful blond.
Sam said I was the only sister who wasn’t with the program. I was so horny I told Sam that maybe it was time for me to get with the program. Soon I was at his house, in his room and naked. We had a great time. His penis was average, about 5 1/2 inches but it felt so good to my hungry little pussy. He had just cum in me for the second time when his cell phone rang. Jake was on the way over. Instead of getting dressed, I waited for him and got to milk his 6 inch penis in my pussy. The two of them gave me at least 6 orgasms that afternoon. They did something I had never heard of, a double vaginal penetration. It hurt a little, but I enjoyed it. I cleaned up in the shower and got dressed. Sam offered to drive me home but I decided to walk, it was only mile.
When I got home, Nicole and my brother were relaxing and snuggling in front of the TV. I must have looked guilty and Nicole said “You look like a kid who just got caught stealing candy or something.” I immediately thought they knew I had been spying on them
I didn’t know what to say so she said “I hope we didn’t make you feel too uncomfortable earlier.” I shook my head. Then she smiled and said “I just talked to Sam on the phone, and he said you got to spend some time with him and Jake.” My brother didn’t say anything but he gave me an understanding smile. They knew I had just gotten laid but not about my spying on them.
That evening, we all went out for pizza, the three guys and their three little sisters. Jake and Ashley said their parents had gone out for the evening so we went to their house to “hang out”. We talked about all kinds of things but the topic came around to sex. They two girls asked me some really direct questions about my threesome with their brothers. I started asking questions about what it was like to have sex with my brother, or anybody with a really big penis. They both admitted that it was uncomfortable the first few times, and that they still need him to be extra gentle. I was thinking in my mind that that’s why I saw Nicole flinch and grimace a few times when I was spying on them.
Nicole gently took my hand and said “I hope you don’t mind but I’m going to give you some advice.” She and Ashley told me that I had jumped into the sex scene way too fast. I didn’t know what they meant and they told me that it would be better if I was more discrete. They, and almost everyone at school knew I had screwed nearly a dozen guys in the first month or so of being sexually active. It’s ok to have sex, they told me, but just don’t give my “enemies” the ammunition they need to call me a slut. They told me to reach agreements with good friends to take care of their needs while they took care of mine. Then I could get laid often by guys who would keep quiet about it. I told them if that was the case, I had probably already ruined my reputation. They said that wasn’t necessarily the case. I could chalk my early promiscuity to being inexperienced and the eagerness to try something new. According to them, a lot of girls go a little wild until the novelty wears off. If I curtailed my promiscuity, I could redeem my reputation. Sex with friends as opposed to just anybody sounded good to me.
Soon, we separated into different rooms. Jake took Nicole to his room, Ashley took my brother to her room and I stayed in the family room with Sam. So we all got to have sex that evening. Again, all the while that Sam was gently thrusting in and out of me, I was wondering how Nicole and now Ashley were managing to handle my brother’s immense penis.
When we got home, our parents asked if we had fun, and commented on how nice it was that we were doing things together. If they only knew….. The next day, the three guys went off somewhere together. I was surprised when Nicole and Ashley showed up at my door and asked if I wanted to hang out. Like I said, I had been friendly with but hadn’t been close to either of them, but recent events were making us closer. I thought to myself how nice it was that I was becoming friends with two of the most beautiful, popular girls in school.
We went swimming, three hot girls in bikinis. I made lunch and we sat around and gossiped for a while. Eventually we started talking about the events from the previous night. I asked again how they managed to take a something so huge into their pussies. I made a big slip up when I said to Nicole your vagina is so small. She asked how I would know that. I confessed about my spying on them. Nicole laughed and said it was no big deal.
The two of them had a threesome with my brother so they weren’t shy about having an audience. I admitted to having a couple of threesomes and that it was a turn on for me to let one guy poke me while another person watched. I also made Nicole promise not to tell my brother about the spying thing. I asked how they got started with my brother.
They said they had heard about his penis and curiosity got the better of both of them, and they both decided to proposition him. Ashley lost a coin flip so she had to go first. I was surprised that the loser had to go first, but they said there was a certain fear factor involved.
Then Ashley asked me “So just how small is your vagina compared to Nikki’s” With that, we stripped off our bikinis and did a comparison. “How cute” is what Ashley said when she saw mine. I was really flattered. We didn’t get into any lesbian action, but we did explore each other’s pussies with our eyes.
A couple days later, I found myself with the two girls again. This time it was at Ashley’s house. She told me she had a present for me and presented me with an 8 inch dildo. I was sure she wasn’t serious. I mean, there was no way she was giving me something like that. She told me I needed one, both she and Nicole owned several.
They insisted that I break it in. I told them I couldn’t so Nicole said she would help me. We were soon all naked, and Nicole spread some sex lubricant on it and gingerly inserted it into her own pussy. Then she told Ashley to lie back and Nicole entered her with it. Then it was my turn. Ashley held my head on her lap. I looked up at her wonderful 35B breasts and she held my hand while Nicole penetrated me with the dildo. I flinched a grimaced like she had done with my brother’s real thing, and managed to accommodate the entire synthetic dick. It did hurt every time she shoved it entirely into me so she gently slipped it out and went down on me. “My god” I thought as this sweet angel performed oral magic on me.
I found myself totally infatuated with these two girls. I wanted to perform oral sex on them, especially Nicole. I’m typically not attracted to women. This situation was special. Nicole’s vagina was every bit as beautiful up close and it had looked from 7 feet away when I was peering thru the window. Ashley’s was nearly as pretty, with pink instead of brown labia. I went down on her, then Ashley before Ashley worked her own magic on me. Until then, the two of them had been very secretive about their lovemaking. None of the guys knew, and no other girl had been allowed to join the. I felt like was part of a secret society. I promised to keep it in confidence. None of us considers ourselves lesbian or bi. We prefer guys, but our friendship continues to bring us together for an all girl session occasionally.
That night I again went out with Ashley and Nicole and we wound up sitting in Nicole’s family room eating popcorn and watching videos. I felt so close and comfortable with them by now. We started talking about sex and thanked them for teaching me how to use a giant dildo and for inclusion in the other activity. I wondered if we were going to do it again right then and there. But they said they wanted to keep it from becoming too much of a habit. They apparently felt some guilt.
I wanted them to describe in detail what it’s like take a really big penis inside and to feel a guy cum that deep. Ashley said it’s hard to describe, it’s something that has to be felt. I asked if they knew any guys with big penises that they could fix me up with. Unfortunately, the only guy in that category was my brother. Nicole jokingly said she might be able to fix me up with him. I laughed and tossed popcorn at her. But the idea of making love with my brother was growing.
The next day, the whole gang came over for a swim. Eventually, we paired up again, I was with Jake, Ashley was with Sam, and once again, my brother took Nicole to his room. I enjoyed being with Jake, and after he came I told him I wouldn’t mind another double penetration. He went to get Sam, and Ashley joined my brother and Nicole. I got my vagina well stretched and well creamed, but I wasn’t getting the deep, deep penetration I thought I wanted.
The gang went home and I felt relatively unsatisfied despite the 4 or 5 orgasms I had just enjoyed.
That night our parents went out. The rest of the gang had family commitments so my brother and I were on our own. I didn’t feel like going out with my other friends so big brother and I were just hanging out at home. I told my brother I wanted to take a late night swim. Our neighbors were also out with our parents so I knew the noise wouldn’t bother them.
He joined me. I put on a thong bikini I had just bought. My mom knew I had it and told me it was for sunbathing in private only. I wasn’t to wear it in public. My brother looked surprised to see me in it but he did say “You look great.” I walked away from him to let him see my fully exposed ass cheeks.
We finished swimming and sat in the neighbor’s hot tub. He asked me how I liked hanging out with Nicole and Ashley, and of course I told him I loved it. He also asked how I liked “that little present” they gave me. I couldn’t believe they told him about my new dildo. We eventually talked about how his sexual relationships with Ashley and Nicole started. I had heard their version, I wanted to hear his. He told me it just kind of started. He had just begun having sex when he was a sophomore. It was with a average looking junior at a party. Once he had sex, the girl told everyone about his huge penis. Soon, a lot of girls were approaching him, some cute, some not so cute. He said it made him feel like the king of the world. Ashley and Nicole were both freshmen and had both lost their virginities, but they weren’t all that experienced. They had heard the gossip and were really curious. One day, Ashley just asked him to have sex with her. The next day , Nicole did the same. Since they’re both so attractive, it didn’t take a lot of convincing. The first few times, neither one could take all of him, but they got used to it.
We returned home and I went to take a shower to rinse the chlorine off. I stood in front of the full length mirror and admired myself. Like I said, I’m quite conceited about my looks. I made a decision. I didn’t put the shorts and t-shirt I had with me on. I wrapped a medium sized towel that barely covered the tops of my thighs around myself and walked out into our basement family room where he was watching TV. He looked at me and kind of raised his eyebrows. I sat on the couch diagonal with him and pretended to watch TV. The towel was barely covering my butt and crotch. I couldn’t believe I was actually trying to seduce my brother, but I was.
He shifted his weight and pulled a part of the newspaper over his lap. Was he trying to hide something?
I asked if he wanted a soda and went to get them. I’m sure when I turned to get up he got a glimpse of my soft, downy pubic hair. I came back, handed him his soda, then slowly sat down again trying to get the bottom hem of my towel to creep up. He smiled and said “You know I can see your pubic hair.”
I looked down and tried to act embarrassed. Then I said something like “When we were little we saw each other naked all the time.” He said “We’re not so little anymore.”. I answered “You’re not the least bit little.”
He laughed and told me I had gotten way too obsessed with the idea of size. I told him I would probably lose my obsession if I could actually experience a big penis. He asked if that was a hint. I nodded.
I told him I just wanted to see it. He thought for a few seconds and agreed to let me see it. Soon I was l seeing his penis for the second time, but this time it was up close. I was only supposed to look, but I had to play with it. It was so big in my hand. He had that look of pleasure as my small hands stroked it.
I just automatically took the beautiful big head in my mouth. He gently tried to lift my head off of him saying this was going too far. I just said “Come on, pleeeez”. He relented and I was trying to take more and more of his shaft into my mouth.
I let my towel fall off and proudly let him admire my breasts. All the barriers fell and we were soon caressing and sucking each other’s most erogenous zones. I spread my legs to let him explore my young vagina.
He scooted me forward so that he could kneel between my legs as he used his tongue to give me an orgasm. Then he stopped for a moment and asked me if I had “cleaned myself up” since that afternoon. He wasn’t all that thrilled with the idea of finding Sam’s cum still in me from earlier that day. I told him I had douched thoroughly so he continued. I looked down past my heaving breasts and watched him give my pussy an expert, gentle tongue washing.
The he rose up and began to gently work his big penis into me. He took so much care to go slowly and gently. The big purplish head disappeared into me, then the shaft began to follow. Each thrust went a little deeper. At about 2/3 of the way in, I felt some pain. I flinched and let out an involuntary “Ahhhh”. He stopped and gave me a few moments to get used to it. Each deeper thrust caused me to gasp and flinch but I was determined to take it all. Eventually I did. He was in too deep for me to absorb each thrust so he backed part way out and fucked me to a depth of about 7 inches. I found the pleasure to be almost overwhelming. I came twice before he buried himself all the way into me and shot a good sized load of cum deep into me. We just stayed there cuddling and being close. We moved to a full missionary position on the floor and he told me that my pussy was even tighter and more sensual than Nicole’s.
We rested, recharged and made love in every position we could think of.
That was the only time we ever made love but I’ll never forget it, and will probably always feel guilty about it.
– The End –