What I’m going to describe is the first time I had an orgasm while making love with a guy. I had been sexually active for about 6 months and had been laid dozens of times by then, but I had never had an orgasm during the act of intercourse. Then it happened. I remember every detail and every sensation so vividly.
The guy was tall and well muscled, his penis long and thick. My fear at being entered by his large penis was unfounded as he was so gentle and patient with me. Unlike previous partners, he didn’t just enter me and begin hammering away in his own frantic effort to satisfy his urges. He entered me with short, gentle strokes allowing me to adjust each time he intruded deeper into me. I looked down between my wide spread thighs and watched as the big purplish head, then more and more of the shaft disappeared into me. It wasn’t just his 8 ½ inch length that was so impressive; the girth was huge. It was at least as beg around as a large banana. The process of entering me took at least 5 minutes, but he was so tender that the discomfort I anticipated never happened.
Once inside of me, he asked how I wanted him to stroke. I asked for long, slow and gentle motions and that’s how he made love to me. He drew back about 4 or 5 inches before tenderly sliding back into me until his groin pressed against mine. I remember, as my pleasure built, I wrapped my legs around him and arched my back to push my hips upward so that I could take him as deeply into me as possible. I heard myself gasping and softly moaning and whimpering with pleasure as his huge penis thrust in and out of me. Then it happened, the most intense orgasm of my life; twice, no ten times more intense than anything I had ever achieved with my own fingers. The orgasm encompassed my entire body as waves of warmth and pleasure emanated throughout my lower regions. His own orgasm flooded me with a succession of powerful spurts of hot semen. I felt my entire body trembling and a wonderful tingling sensation ran up and down my spine and my inner thighs. At last, I understood just what all the uproar was about. He kept his penis buried deep inside of me, gently flexing his penis to pump the last droplets of his semen into me. His arms gently cradled my shoulders as he held me close and he gave me a long, loving kiss.
The problem was that this gentle, skilled lover of mine was also my older brother. It was nearly four years ago when this all happened and I’m still torn between cherishing the moment, and several similar ones that followed and the guilt of being involved in such a taboo relationship.
What inspired me to write this story is that I’m a psychology major. One of my professors told us that it’s useful and healthy to confront our own most difficult issues by writing our thoughts down. It can have a cathartic effect, even if the writings remain themselves remain private.
I’m currently 20 years old and I just finished my sophomore year of college. You could say that I have a very active and enjoyable sex life. The longest I have gone without getting laid since I started college has been about 6 or 7 days. These short droughts usually occur around mid-terms and finals when most of us are too busy studying. The term all-nighter really does refer to studying around test time. Otherwise, I like to have sex two or three times a week. Even though I’m not in a serious relationship, I have a number of good male friends who share “benefits” with me. I’ve spent my share of Friday or Saturday nights engaged in sexual all-nighters. I credit my ability to have mutually satisfying sex to my ability to communicate with my partners. Over time I’ve learned that any guy who is worth being with actually appreciates being told how to be more skillful lovers. If a guy doesn’t care enough to listen, then he doesn’t get me in bed with him. I give my brother credit for teaching me to communicate during intimacy.
My first experience with intercourse happened nearly five years ago toward the end of my freshman year. The guy was three years older than me and a popular jock who wasn’t all that interested in making sure I enjoyed it. At best I was just a convenient and available pussy with a cute face and decent body attached to it. I felt proud of myself afterward, it was a big step in my life. Fortunately his penis wasn’t all that big and the pain was minimal. The physical pleasure and satisfaction I felt was minimal. We had a bit of foreplay, but not enough to make me climax. The most enjoyable part was all the compliments, spoken and unspoken, he gave me. His eyes lit up when he saw my breasts. He told me how nice my body is and how good it felt to have his cock inside of me. I was so pleased when I felt him ejaculate; making a guy cum seemed like such an accomplishment.
I found that orgasm or not, having sex was a great boost for my ego. I’m pretty enough, some people tell me I look a little bit like Katherine Heigl although at 5-2, I’m not as tall. My hair is light brown, my eyes are green and I have a bit of a sultry look. I have shapely, if not exceedingly long legs, a great ass, and a curvaceous 35C-35-36 figure. Getting naked in front of a guy and seeing the look of excitement on his face when I unveil my body is a pleasure I’ll never get tired of. Even guys who have seen me naked many times over get that look.
Finding opportunities to have sex wasn’t very difficult given my relative degree of attractiveness. It was the beginning of summer so guys had plenty of chances to see me modeling my bikini collection down at the lake, or walking around town in cutoffs and short, sleeveless t-shirts. Summer was like a buffet of cute guys to choose from. I had 5 sexual partners in the first month of summer break. After that I started to worry about my reputation so I tried to be a little more discrete. I have 3 good friends that I had known since elementary school, and they became my primary sexual partners. At first it was one at a time, but toward the end of the summer I got bold and pulled train for all three of them. I loved the attention and the knowledge that every time I doled my sexual favors out, they guys would respond like hungry puppies. It gave me such a sense of power over the “stronger” sex.
The problem was that I wasn’t having orgasms. I always went home frustrated after having sex and wound up masturbating. My brother and I have a friend, Annie who lives across the street. She’s a tall, willowy, beautiful blonde with legs that seem to go on forever without end, a cover girl’s figure, and a face so lovely men gasp and women envy her.
She and my brother are the same age, they were born days apart, so she’s closer to him than me. They have more or less been best friends since I can remember, and when they were sophomores, they became sexually intimate with each other. I learned about their relationship about a year after they started, and a year before I lost my virginity.
Both Annie and my brother knew I had become sexually active, in fact they are the ones who made sure I understood how to use birth control. One afternoon, in late August Annie and I were hanging out and the conversation got around to sex. She asked me how my sex life was and I confessed that I was having a problem achieving orgasm. I had been laid dozens of times by then but had never climaxed during the act. I was having fun, and there was pleasure from being caressed, and having my neck, shoulders, breasts, tummy, and thighs kissed. But no guy had ever gone down on me and no guy had ever used his penis as an instrument to make me achieve orgasm. I had come close a few times, but the guys would generally ejaculate before I got to where I wanted to go.
Annie told me the problem was that the guys I was choosing either didn’t understand or care about what my needs were. It may have been lack of experience or a simple lack of consideration.
She told me something I probably would have been better off not knowing. She said that my brother is an incredible lover. He was not only well endowed, he was also extremely caring and considerate in bed. Annie said the orgasms she enjoyed when she made love with him were mind blowing. They weren’t a serious couple at the time, just very good friends with benefits and they both had sex with other partners. As I described earlier, Annie is a knock out. My brother is one of the hotter guys in at our school so neither ever suffered from a shortage of prospective sexual partners. Annie said that my brother was by far the best she had ever had.
A few days later my brother went to hang out at Annie’s while her parents were out of town. He was going to keep her from getting lonely. My mother told him to have a good time and to stay out of trouble if she only knew. I had to keep from laughing when she said Annie should come over and sleep in the guest room when her parents were out of town. Like I said, if she only knew.
The idea that Annie was going to be having mind blowing sex left me feeling frustrated. I called my friend Andy, and as luck would have it, he had another one of my friends, Cameron with him. These were two of the guys I had been having sex with occasionally. I told me parents we were just going over to the mall to hang out. What we actually did was sneak into Andy’s parents camper and have a threesome. To my surprise, I did have a mild orgasm. It wasn’t during the act of intercourse, it was during the foreplay when Cameron went down on me. Yes, at last a guy went down on me. It wasn’t the mind blowing, ground shaking orgasm I had expected and I went home frustrated. I masturbated before drifting off to sleep, then awoke in the middle of the night and masturbated again.
The next day, while our parents were at work, Annie came over and of course she and my brother went up to his room to make love. My friend Dave, the third of my close guy friends who received sexual benefits dropped by. I was so ready for sex that I took him up to my room. Now even though Annie and my brother knew that I was having sex, this was the first time I had ever done it in the house while they were around. In a way is was a rite of passage. I talked Dave into going down on me and he did give me a nice little orgasm. Unfortunately, the intercourse itself lasted only 3 or 4 minutes and I didn’t come close to climaxing.
My frustration was mounting. After Dave left, Annie, my brother and I were sitting in the kitchen drinking sodas when Annie gave me a gentle hug from behind and said “So tell us, how was it.”
I didn’t want to discuss my latest sexual encounter in front of my brother but Annie prodded me, saying “Don’t be shy, he knows all about your problem.”
I couldn’t believe it, she was telling him about my sex life, and I was mortified. My brother laughed and gave tussled my hair like he’s done ever since I can remember and said “You’ve gotta take control and tell the guy what you want.”
I got embarrassed and left the room. A few minutes later my brother came and found me and told me he was sorry for embarrassing me. I told him the problem wasn’t embarrassment, I felt like my lack of satisfaction was my fault. I couldn’t tell the guys what to do because I didn’t know what to ask for.
He said “Well, maybe you should talk to Annie about it, she thinks of you like a sister and I know she’ll want to help.”
Annie and I did have a talk later that evening and I told her I didn’t feel comfortable telling another person what to do. She gave me a hug and said “Well, imagine I’m a guy and talk to me.”
I wasn’t sure what she meant so she told me to get undressed and tell her where to touch me, how to caress me, etc.
I was dumbfounded, expecting her to tell me it was a joke. Instead, she slipped her shorts, panties and bikini top off and stood in front of me looking like a goddess. She said “Come on sweetie, pretend I’m a guy and talk to me.”
I swallowed hard and took my clothes off. Soon we were caressing each other, and with her encouragement I told her where to touch me, how to caress me, how firmly to rub or press as she masturbated me. I also had my first experience having another woman go down. Her tongue swirled around my clit and gently washed over my labia. The sensation of her tongue penetrating me so sweet. She also told me that part of being a good lover is listening to my partner, and soon I was doing her bidding, giving her pleasure. I remember so clearly the close up view of her lovely vagina, and taking my first loving taste of it. I kissed her tummy and thighs between the long tongue jobs I gave her labia and clit. Her beautiful B cup breasts were a delight to suck. I had never kissed another girl until that night, but I can honestly say that her kisses were the sweetest I had ever experienced. When we finished she hugged me and said “See, good sex is all about communicating.” I went home confused, wondering if I was going to turn into a lesbian.
Of course, I discovered it doesn’t work that way; bisexual maybe, but not a lesbian. Over the next couple of weeks, we made love several times. She and my brother made love almost daily. One evening, just as I started to go down on her, she giggled and said “You know, I haven’t showered since your brother and I made love, you’re probably tasting his cum.”
I hesitated for a moment but she said “Oh go on, it’s not going to kill you.” I continued and took her to a climax before she returned the favor.
Even after all of that, the idea of talking to a guy, ordering him around during sex still made me feel uncomfortable.
One morning, while my brother was out, Annie came over and we made love again. We then go into our bikinis and went out to the back yard to get some sun. My brother came home and seeing Annie in her bikini got his blood flowing. He suggested to Annie that they go upstairs and she said in a joking tone “Jeez, first I have to do your sister, than you.”
I was horrified. She was announcing to my brother that she and I had been lovers. She looked and me and said “Sweetie, he knows he’s known since the first time we made love.”
“Why didn’t you tell me?” I shrieked.
“Calm down” she said “It’s not like he’s going to tell anybody.”
“You’re lucky” my brother joked “Annie doesn’t sleep with just any girl guys yeah but nut just any girl.”
Annie gave him a loving smack across the back of his head telling him to watch it or he wouldn’t be getting any. The two of them headed hand in hand upstairs.
A minute later Annie, completely naked, came down stairs looking for me. She took my hand and said “Come on.” I pulled away saying “What why?”.
She told me “Just come with me, I’m going to show you how to talk to a guy.”
Before I knew it, I was watching her and my brother putting on a show. She instructed him, telling him which breast to suck, to nibble her nipple a little harder, to stick his tongue in her and move it rapidly. He was wearing his boxers during all of this, but I could clearly see the huge bulge.
He was so ready for making love with Annie and he looked at me and said “OK, time for you to give us some privacy.” I started to leave but Annie said “Wait why does she have to leave?”
My brother said “I can’t do it with her watching.”
“Why not, you’ve performed in front of other people.” Annie replied.
There were so many revelations being made that day. As I found out, the two of them had stage several sex parties with several other couples, and Annie had done a train for 7 guys, including my brother once. But I’ll tell those stories some other time.
“Let her watch” Annie urged.
By now my brother was so horny he just wanted to begin making love with Annie, so he stripped off his shorts and I saw the biggest penis I had ever seen. By that time in my sex life, I had gone all the way with 11 different guys. Eight from town, including the three friends I already mentioned, plus two guys I met at camp, and a cute guy I met when my family went to Yellowstone for a vacation. None of them had a penis longer than about 6 ½ inches. My brother’s has already been described.
I watched in fascination as he slipped it into Annie and responded to her requests of “slower, more gentle, now harder, faster etc.”
He obviously loved the orgasm she gave him as he gasped in pleasure and arched his back to push his hips down toward her. She pushed up to meet him and I knew that every fraction of his penis was deep inside of her. They then made love in a variety of positions. I knew doggie and cowgirl, but they showed me the spooning, pile driver and a number of variations of missionary that I had never seen or imagined. Most of my experience was flat on my back.
I had stripped off my bikini and was wildly masturbating and playing with my nipples. I didn’t care that my brother saw me naked.
When they finished, Annie invited me to go down on her. I did, eagerly despite my brother’s freshly deposited semen. She returned the favor and I found myself not even caring that my brother watched. He got a close up view of my vagina, and Annie even stopped and asked him “Don’t you think your sister has a pretty pussy?”
My brother said “It’s beautiful so are her breasts” Annie asked if there was anything else that he liked about me and my brother continued that I have beautiful legs, a beautiful figure and a perfect ass. Incredibly, after all that had gone on, I finally felt myself blushing, but it was nice to hear.
After we had gotten dressed and Annie had gone home, my brother and I acted as if nothing had happened. We even got into an argument over something silly at dinner and my dad said “You two sound ridiculous, try to get along.”
He had no idea just how well we had been getting along.
Two days later, I couldn’t stop obsessing about my brother’s big penis and what I had watched him and Annie doing to give each other mutual pleasure. Our parents had left for work and he was still sleeping. I slipped my t-shirt off, and quietly walked into his room clad only in panties.
I woke him and asked if I could join him the rest you know.
It was the first of six times that we made love back then. We decided to that it wasn’t a good idea to continue, but we have given in to weakness on occasion . The last time was on his birthday a few months ago. He, and Annie and I had a threesome. I felt guilty about it but that didn’t stop me. By the way, he and Annie are engaged so we’re definitely strengthening our “Family Ties”.
– The End –