Philip was only fourteen when his slightly older sister discovered how he had grown since they last played doctor. She was flabbergasted and couldn’t wait to get her hands on the erection that popped out when he dropped his drawers. She’d touched his “pee-pee thing” a lot but wouldn’t apply her mouth or pussy to it in earlier times. Now it was way more than twice as big. She got a tape measure and got eight-and-a quarter inches long and slightly more than three inches wide at mid-shaft. She had played with a few other guys and was astounded at the difference. Right then is when she named it “King Dong”.
She had to tell her best girl friend who was VERY interested. She’d been brave enough to actually fuck a couple of guys and wasn’t very impressed with their small equipment and lack of skill. Tracy kept bugging Philip’s sister, Wendy until she invited her over after school. Both of them walked into Philip’s room and Tracy gave a loud squeak. Philip was sitting in front of his computer with his hand rubbing his fully engorged organ as he watched some porn.
Without even an introduction Tracy knelt down next to him and got a mouthful of virgin male meat. His eyes went wide and he stopped his own stimulation to watch. This was so damn much better and something he had certainly fantasized about. All he could see was the curly brown hair on the back of this girl’s head. What he could see didn’t matter compared to what he was feeling and he didn’t give any warning when his prostate let loose.
Tracy gagged a bit but gamely swallowed it all and finally raised her head. When her mouth was empty she smiled and said, “Hi! I’m Tracy and this is what I came to see. It’s even better than I expected.” She was hot and on a roll so she just kept talking, “I’d like to see if that thing will fit in my pussy. Interested?”
Does the sun rise in the East? Philip only had the ability to nod so Tracy stood up and stripped, then headed for his bed and laid back in the classic invitation position. Philip hadn’t lost a millimeter of his erection and vicariously knew where it was supposed to go. As the huge shaft approached her young and lightly used snatch, Tracy had second thoughts. “Wait a minute, let’s try a different position. You lie down and let me be on top.”
Philip could’ve cared less the orientation if he was going to get in a real pussy so he complied quickly. Tracy was pretty wet already but she was only able to get the head inside after a bit of effort. That was enough to set Philip off again and he flooded her with semen. That softened him slightly and added lots of lubrication so his rider kept moving up and down, gradually accepting more meat. She only managed half of it before her own orgasm shook her violently from head to toe and she got another pussyfull of sperm. She kissed him goodbye and said, “I’m coming over again next week.” Said, not asked. Like he would really object?
Philip and his sister had a lot of fun talking about that because she had witnessed the whole thing. The next week Tracy was able to carefully embed the entire “Dong”, explaining she’d stretched her pussy with larger and larger objects since her last visit. She was concerned that it might ruin her for any other lovers but now is now, and that was the future. This time she got three copious loads of his cream in three different positions.
She was visiting twice a week and they were having a delightful time. All of a sudden, though, she disappeared without notice. Wendy asked around and found out that she had been sent to live with her aunt for a while. No one had thought about birth control apparently.
Tracy’s bragging had stirred up interest among some of the other girls. I need to mention that these were all Philip’s sister’s age or older. Many of them already had sexual experience and were still in an exploratory phase.
Being careful to verify that birth control was in use, Wendy began bringing over new and curious visitors to Philip’s bedroom every week. It was a teenage boy’s dream. He didn’t have to chase pussy, it was chasing him!
Once that age group had gotten her jollies, which was mostly what they wanted, word-of-mouth brought a round of college girls to try out King Dong. Some of them were even married, as evidenced by their wedding rings although they never overtly admitted it. Those were actually more likely to come back for more than the single ones who had other peckers to explore. Some of the wives were just curious and some of them were just not well satisfied with what they got at home. The latter were ones that Wendy worried about because she didn’t want any emotional attachments for her young brother at this time.
A number of things had evolved since this story started. Wendy had gotten a job and her own apartment not too far from their parents’ home which made her brothers assignations much easier to arrange. The hornies she got watching her brother with all these women gradually overcame her own reservations. She’d long used her mother’s dildo on herself while she watched brother banging these happy women. The next big step was to persuade him, with her very first blow job, to buy her a dildo approximately the size of his organ.
That up and opened another sexual avenue for her as well. She dated but no one had ever gotten past third base. Oral sex was OK with the right guys. Now she orally cleaned him after his copulations and in a few cases even did the same for the woman he had just pleased so mightily. Her orgasms were plentiful from all this vicarious stimulation.
For her 20th birthday she took the big plunge and after all the family celebration, she took him to her apartment in the bed where he had now screwed a couple of dozen different women. “Brother of mine, it’s time that I became a full-fledged woman and I’ve always wanted only you to have that honor.”
Philip hugged and kissed her, “I’ve waited a long time for this and I am thrilled to share everything I’ve learned with the woman I love the most dearly in the world.”
Suffice it to say that their coupling was at times tender and loving, and at times vigorous and wild. They tried and did everything they could until they collapsed. After resting they went at it again. They stopped to eat and briefly tend to bodily needs, but even then King Dong was buried in Wendy when she peed. She perched on his hardon as he sat on the toilet with her hot liquid running down over his balls. When his amazing pecker finally failed to rise, they went back to some of the pee–games they had played as young children. All in all, it was the best birthday either one could imagine and they vowed that both of theirs should be celebrated that way from now on.
The age progression continued and Philip was now screwing women in their late 20s and early 30s, some married, some divorced and some neither. A few tried hard to put their hooks into him but he had learned how to resist those entanglements. Their mother was so pleased that brother and sister were spending Sunday afternoons together without realizing exactly why that was happening so regularly.
Philip completed high school and went on to community college. His sister lived much close to campus than his parents and that justified him moving in with her. Mom was so pleased that they got along so well.
He was curious about older women now, even his mother’s age, so made it a point to socialize with the non-traditional students. They were often thrilled with his attention and complements and the ones he found attractive were more frequently than not receptive to getting better acquainted. Of course, once they saw what he was offering, they either ran or “assumed the position”. He preferred the married ones because of the reduced chance of entanglement. It was also fun to hear their sexual histories, some of which were quite stimulating.
Dong got regular exercise with a few favorites in addition to the Sunday-sibling screws, not that they had to, or did, wait a whole week. Wendy tried a couple of alternative dicks but they were sadly lacking so just stuck with the best. She’d told him, after those incidents, that she might just have to be his-mistress-for-life.
Marsha surprised him, though. Married over twenty years and the mother of two teenagers not much younger than Philip, she really clicked with him and not just at the genital level. Her husband travelled a lot and she explained her interest as more than sexual even though she’d never had such a well-endowed partner. Of course, few women had. A horny redhead before marriage, she’d not let them get very long when her husband began to be absent so often. He was average in bed, she reported.
This bright and perceptive woman quickly figured out what their mom hadn’t; that they were screwing-siblings. She’d experimented with both her older brothers at an early age but they’d all moved on. Some of the thrill for her was also semi-incestuous, thinking about her son as she screwed Philip, but that was incidental. She and Philip just thought alike in spite of the big age difference. They had some of the same classes so studying together brought them closer than the frequent coital romps.
Usually their meetings were planned in advance. Philip had other obligations as did she, but one time she texted an urgent request for an immediate visit. Philip quickly finished up with the woman he was pounding and sent her on her way just moments before Martha appeared. Without a word she led him to the bedroom and stripped off the only garment she was wearing, pulling Dong into a soaking snatch. “Fuck me hard. Give me your seed!”
After she calmed down, which took two orgasms and a filling of semen, she explained, “My husband gave me an all-too-rare quickie before he left for work.” She glanced at her watch and continued, “About fifteen minutes ago he put his sperm in me and I had an overpowering urge to have two-in-a-row, something I’ve fantasized about ever since my brothers did it to me so long ago. Thank you! Thank you!” She kissed him long and hard and he felt the deep feelings behind it.
Phillip made guy friends at school too but didn’t do much with them since women kept him so occupied. There was a big brown-skinned guy he enjoyed visiting with. Raul was a South American exchange student and gave him an insight to another culture for the first time. They’d go for walks in a nice wooded area at the edge of campus when the weather permitted. On one such walk Raul interrupted, “I must pee here. I can’t wait.” He hauled out a big hose and watered the shrubs with no concern for modesty.
Watching that made Philip do the same for other nearby plants. He’d had a good look at Raul’s tool and asked, “How big does that thing get?” The answer was twenty centimeters which converted to almost as big as his own.
With the subject opened, Raul began complaining that he was having little luck getting laid between possibly racial issues or a fear of his big dick if it got that far. Philip told his friend, “I’ve got some ideas to check out. I’ll get back with you in class tomorrow.”
When he told Wendy about his discovery she exclaimed, “When can I meet him? Can you bring him over tomorrow night?”
Raul was so polite and intimidated by this attractive slightly older woman that he really held back. Wendy knew how to take charge and finally just came out with it, “Philip tells me that you are a well-equipped man. That is exactly what I am looking for. Am I attractive enough to get your interest?” When he nodded she led him to her bedroom. They didn’t surface for two hours.
Philip stayed out of sight as she bid Raul goodnight and then met his naked and well-used sister at the bathroom. She had to drain both bladder and box, then ordered her brother to get his dick in where “it would do her the most good”. She screeched and shook and he pounded her somewhat tender tissues, babbling about how goddam sexy it was to screw two big dicks in a row. They slept for a while.
She was full of wonder at the happenings and anxious to do it again. As he filled her cunt she had called him “Raul” and he understood. When things calmed down, Philip wondered if Martha would enjoy him too.
Wendy respo0nded with, “Shit, how could she NOT? I’m not sure I want to share though. He’s as good as you and when I asked him why he said that back home he serviced several wealthy married women whose husbands had mistresses. They were paying his expenses for being here. Can I keep him to myself for a while?”
“Anything for my loving sister. Speaking of which, will I still get all I want of your treasures?”
“Of course, silly. I don’t think both of you together could wear me out. Hmmm, I’d like to try that sometime. I’ll propose it after Raul and I get more used to each other.”
Of course Martha met Raul and one time when she was exiting the bathroom as he was entering, naked after banging Wendy, she got back in bed with Philip commenting, “Geez! That guy looks like he has as much to offer as you do. I wonder if he’d be interested in an old chick like me?”
Philip gripped her pussy and said, “I’ve heard that he’s had lots of experience with mature women but Wendy ain’t sharing yet. Be patient though.” She came from his touch.
It was unusual for Martha to visit him on a Saturday but she texted one afternoon and wanted to see him right away. Wendy was home and was asked to join the still-clothed woman too.
“My husband and I just had a long-overdue talk. He just got back from a trip and said that he had some things he didn’t want to hold in any longer. Apparently he often went with mixed-sex teams on these sometimes multi-week projects. He said that there was usually at least one woman who liked to make sure that none of the men got very horny. Some were married and some not. They were popular enough that he’d get a piece only every other day or so. No romance, just sex. He apologized and hoped I loved him enough to understand.
“I told him I certainly did and I was mostly unhappy he didn’t tell me sooner. Then he discovered that he wasn’t the only one who had compensated for partner absence and that I’d been getting some satisfaction for only the last few months. Neither one of us offered or asked for more details yet but he took me to bed and I got a rare mid-day screw. Twice, actually, just a little while ago. It hasn’t been said yet but I think we are going to agree that what we are doing is necessary under the circumstances as long as it doesn’t hurt our marriage. For you and me that is going to mean that I won’t fuck you when he is in town. Believe me, I’ll miss it but we must continue the other aspects of our friendship.” She kissed me and left.
We were both quiet for a while, then Wendy came into my arms. “She really loves you. I can tell. But she loves her husband too. I guess you can love more than one person at a time. Maybe, like good fucking, each one is its own unique treasure. I’m getting some feelings for Raul besides my crotch. Speaking of which, do you have time for a romp?” Yup!
Martha’s husband was gone for a week and she took every opportunity to get laid she could schedule. It was even more satisfying now that the slight overly of guilt had been removed. Although she asked, Wendy wasn’t ready to share Raul yet but didn’t rule it out in the future, remarking that there would be a bit of fairness in that.
Another Saturday surprise meeting. Raul was there too but that didn’t slow Martha down although she wished he was naked. She had lots to tell.