Choosing a Stepfather

by “Brad Gillespie”

Author's Note:

I apologize if this story isn't as hot as a lot of the others you see here. But there are a lot of others who, I think, are better at story-writing than I am. I prefer to come up with story ideas and have someone else fill in the details, and this story was originally intended to be a collaboration of that type. However, the person I had hoped to collaborate with on this gave me a draft of a first chapter that was so different from what I meant this story to be that we gave up on collaborating. I still think he's a better story-writer than I am, but obviously this plot doesn't fit into what he'd like to write, and I couldn't find another collaborator, so I'm trying to do this on my own.

The usual disclaimer about how this is purely fictional and none of the actions, persons, and places in the story really exist (except, of course, that there is really a West Coast, and a Los Angeles airport!) applies.

Send all feedback to the address RBZ followed by the digits 3141 at Please put the story title in the subject line. But don't be surprised if the name on the responses is different. That e-mail account is under a different pseudonym than the one I used to write this story.

Also, anyone who would like to collaborate with me on a story, send a note to the same e-mail address as in the previous paragraph. I’m really hoping someone might be willing to collaborate who can take a story like this (probably in brief outline form) and write in the details to make the kind of hot erotica that you see a lot of on here.

Connie and Bob

Connie and Bob must have been one of the happiest married couples there ever was. Bob was a practicing lawyer, pulling in enough income to make a nice lifestyle for the couple. For a few years, though, they were childless, although both of them wanted a child. It wasn’t that they weren’t trying: they probably had sex as much as any married couple on the planet, and never used any sort of contraception, because they really were hoping to have a baby. Then, after six years of marriage, Connie finally had a baby son. He was named Timothy, nicknamed Timmy, after Connie's grandfather, who had died just a month before Timmy was born. Connie was extremely happy, and not just because he was hers; he was a little bit of Bob, as well, and as she loved Bob, she loved anything that was connected with him, especially little Timmy. As Timmy grew up, Connie used to say that Timmy was the handsomest guy on the planet — except, of course, for Bob.

Since Bob was relatively well-to-do, he was able to buy a big house for his family. There were so many rooms that some of them never got used much; any time someone visited the family, of course, they got their own bedroom to sleep in, and a bathroom of their own. Both Connie and Bob had several brothers and sisters, and Timmy got to know his aunts and uncles very well.

Shortly after Timmy's 5th birthday, Bob had to make a business trip to the West Coast to deal with some client business. The plane crashed on the approach to Los Angeles Airport, and when Connie heard the news, she was devastated. All she had of Bob was his money (Bob, of course, had insured his life heavily) and his son. The love that Connie had for Bob was directed toward Timmy, and Connie became the most devoted mother you'd ever see.

Connie, the single mother

So now, Connie had to take care of little Timmy all by herself. There was nothing she wouldn't do for her adorable son, and with the money from Bob's insurance she made sure he had whatever he needed in clothes, toys, and everything. One thing Connie worried about was that a boy growing up with a single mother might have problems with the absence of a male role model. Connie had a brother in the same town, Melvin, but she was not sure Mel would be a good role model for Timmy — Melvin was openly gay, and Connie wondered about that. But she never got in the way of Timmy's bonding with Uncle Mel, because her attitude was always “if Timmy wants something, and I can get it for him, he'll have it.” And it was clear that Mel loved his little nephew, and Timmy loved his uncle, and that was what really mattered. When Timmy asked about the fact that his Uncle Mel never married, it was explained that while his dad had loved Connie in a special way, Mel didn't feel that way about women, and so he never could get into this type of relationship.

As Timmy got older, he decided that he felt about the same way as his Uncle Mel about women. Sometimes Timmy would talk to his uncle Mel, and it was in these conversations that Mel had explained to him about being gay, and it was from that that Timmy had concluded he was the same. Whenever he had visited Uncle Mel, if he had had a guy over, he would introduce him to Timmy, explaining to the friend that Timmy was his nephew, of course, and most of the men would be friendly — but Timmy would have daydreams about what Uncle Mel and the friend were doing when they went behind closed doors. He found these men much more attractive than girls — or boys — his own age, and while none of them had actually done anything sexual with him, he had some pretty good ideas of what they were doing with his uncle. As he grew older, he had daydreamed more and more about what had gone on behind closed doors in his uncle’s bedroom when a “friend” had been over, and it had gotten to the point that it wasn’t just daydreaming — he would be thinking about it every night before he went to bed. At some point he had been drying himself off after bathing, and by rubbing his penis with the towel, accidentally discovered the pleasure he got playing with himself. Now he found that every night, before he drifted off to sleep, he would play with himself and think of one of the handsome men he’d met at Uncle Mel’s house. Sometimes it would bring him to a dry orgasm, a feeling he really loved, and the fact that he could get that from thinking about Uncle Mel and his “friends” convinced him that he was gay just like his uncle.

So about five years after the accident, he came out to his mother. Connie was not terribly happy about Timmy's being gay, and thought that at age 10, he might not be ready to self-classify, but her love for her son was so great that she vowed she'd accept whatever he told her he was. He told her about his conversations with his uncle, and his fantasizing about his uncle’s visitors, and Connie felt that whatever Timmy was, he was her adored son, and she was not going to change him, so she had to accept him fully. And she was never critical; after all, her own brother was also gay, and she loved him as well, so she’d come to realize that just because a person was gay didn’t mean there was anything wrong with him. If she had any negative thoughts about Timmy's sexuality, it was that others might not accept it — she knew there was still a lot of homophobia in this world.

The proposition

Several months after Timmy's 10th birthday, Connie and Timmy were talking about things and Timmy asked her why she had not remarried, after 5½ years of lonely single life. She told him she could not consider marrying again, because her love for Bob's memory was still so great. But she was thinking about something that she had read about. She knew that there were gay men who entered into “marriages” that were not real, so that their sexual orientation wasn’t obvious to the whole outside world. And she’d seen Timmy come home from visits with Mel, ecstatic about someone of the male friends Bob had. So she put forth a proposition to her son. “If you can find — whether by your Uncle Bob’s connections with the gay world or anyway else — some man you really want to be with, all the time, I will marry him on paper,” Connie proposed to Timmy. “He’ll be — officially — your stepfather, so you’d have no reason to hide your being with him a lot. And he’d live somewhere in this house — not in my bedroom, of course, though none of the outside world need know that — so you could see him all the time. And in a way, this would help me too. You’re not the only person who wonders why I remain alone 5½ years after I was widowed. I get questions from all sorts of nosy busybodies, none of whose business it is, and this would end these nosy questions.” Timmy was overjoyed. “You mean I get to have a lover? A real lover, that nobody can take away from me?” But Connie cautioned, “You’ll still have to keep that secret from prying eyes. Sex between adults and young people is condemned by most of the world. And between a man and his stepson would even be considered worse. But nobody needs to know what’s going on in the bedroom. The thing is, even in public you’ll be able to show affection — that is considered normal. And you’ll be living in the same house, so you can see him any time he’s not working.” Timmy responded, “You’ll do this for me? Mom, I really love you for this.” And Connie replied, “I love you so much. Anything I can do to make you happy, I want to.” Timmy couldn’t get to sleep that night without hours of playing with himself, fantasizing about the man he would get to pick out as a stepfather.

The next day, Connie called up her brother Melvin, and asked him to come over. When he arrived at his sister’s house, both Connie and Timmy were there, waiting to have a heart-to-heart conversation with him. Connie explained the plan, telling him that, because he was gay and knew a lot of other gay men, both intimately and not, he was going to be important in seeing that Timmy could find the man he was looking for. Melvin responded that there were many predatory men about, and he would hope he could screen the men that might want to be Timmy’s “stepfather,” to make sure that they had no desire to do anything that would be painful or unpleasant to Timmy. He told Connie, “I know a lot of gay men, but only a few who are really ‘into’ boys, so I’ll have to do some digging. The man we find will not necessarily be someone I know right now, but I know how much you love Timmy, and I want to make sure this plan works to his benefit. Besides, I love my nephew too.” And he looked at Timmy, and hugged him. “I hope you’ll trust my judgment,” he said. To which Timmy responded, “I’ve seen the men you’ve chosen as your own ‘friends.’ I think you have really good taste. Of course I’ll trust your judgment.”

The search

For months the search went on. Sometimes it would be a man that Melvin knew, that hadn’t done anything sexual with Timmy when he’d been over, and Mel would sound him out on what he thought of Timmy. But usually those men weren’t “into” young boys, just as Mel figured, and so they weren’t likely prospects. And the few he knew that seemed open to the idea of man/boy love had different pictures of their “ideal” boy than what Timmy was: they wanted a real jock, or a “sissy” boy, and Timmy wasn’t either. One of the men was a strong anti-circumcision fanatic, and when he saw Timmy’s very obviously circumcised penis, he berated Melvin, who of course could say nothing more than that he wasn’t Timmy’s father, and that that decision had been made a long time ago by his parents. That man simply stormed out of Mel’s house. Melvin was sure this was not going to pan out. He tried getting suggestions, from his gay friends as to other men they might know, but the same things kept happening. And once in a while he actually found a man who was interested, and he’d leave them alone together while he went “out on an errand.”

One memorable occurrence involved a man named Ken. When Ken was alone with Timmy, he undressed immediately and ordered Timmy to suck his cock. That wasn’t the kind of relationship Timmy envisioned, and while Timmy complied, mainly out of fear, because his uncle wasn’t there to intercede, when his uncle returned, Timmy told him what had happened. Melvin asked Ken whether this was true, and Ken cheerfully admitted it: “Boys are supposed to be submissive, aren’t they?” Melvin ordered Ken out of the house, and told him that was the last time he’d ever see Timmy.

One day, however, something different happened. This involved a man who hadn’t even been one of the prospects that Mel was considering for the role of Timmy's stepfather. Daniel Jennings was simply a man who had come over to make some estimates on a repair to Mel’s boiler. Mel had generally made it a practice to patronize “LGBT-owned” businesses as a matter of “pride,” so Mel assumed Dan was gay, but this wasn’t a day that Timmy had even come over to “interview” a prospective stepfather. While Dan was in the basement looking at the boiler, Timmy happened to come over, and Mel wasn’t even thinking of matching Dan and Timmy, but simply was going to enjoy “normal” uncle-nephew interaction as long as Timmy was there. Dan came up with his notepad, expecting just to give Mel his estimate and go, but when he saw Timmy, he exclaimed, “And who is this?” Mel told him it was his nephew Timmy, almost 11, and Dan exclaimed, “What a handsome young man!” Timmy whispered in Uncle Mel’s ear, “What about him?” Mel whispered back, “I really don’t know him: his name is Daniel Jennings and he runs a contracting firm, and that’s all I know.” Mel said to Dan, “I know you have to go to your next customer, but Timmy seems to want to get to know you. Could you come back sometime when you’re ‘off the clock’?” And Dan said, “Yes, I’d love to.”

The next weekend Dan called Melvin, and asked if he could come over to talk with him and Timmy. Mel was happy to have him over, and called his sister to find out if Timmy could come over as well. The three of them had a long conversation. Dan told Mel that he’d never seen such an attractive boy, and Timmy blushed. He, in turn, thought Dan was pretty attractive, too, and told Mel he’d like to spend some time with him to get to know him better. As usual, this was the cue for Mel to find some errand he needed to take care of, and he told Dan he could stay there and “talk” to Timmy while Mel was out. He winked at Dan when he said “talk,” so Dan understood that if he wanted to go beyond just talking, this was OK with him.

Unlike the time with Ken, say, this time it was just talking for a while. Dan really seemed to want to get to know Timmy, not just have sex with him. He asked about school, hobbies, and many other things. And it was actually Timmy who got impatient, reaching over to stroke Dan’s cock through his pants and underpants. Dan responded, “Whoa, Timmy! You do that and I’ll mess up my clothes!” And Timmy realized by that statement that Dan was sexually interested, but just holding back. They both got undressed, and played with each other’s dicks, until Dan came, and Timmy had a dry orgasm — as mentioned before, he loved these, though he didn’t get them as often as he wished. Timmy marveled at Dan's 6½ʺ long dick; it seemed pretty big to Timmy, of course, though it was really not more than about average for an adult. By the time Mel returned, both of them had gotten dressed, but Timmy made it clear that he’d like to see Dan again. Dan was a bit afraid Mel would object, but after all, he’d left the two alone together, and he must have had some idea of what would happen, so he put his fears away. And Mel told Dan, “Timmy likes you. That’s the only thing I want to know. What you do when you’re alone — here he winked at Dan, to show he had a pretty good idea what had happened — is your own business. If Timmy doesn’t have any problems, I don’t. And,” he added, “neither will his mother. I know my sister. She only wants for Timmy whatever makes him happy.” And he told Dan Connie’s address, and indicated that as long as Timmy said he was welcome, he’d have no problems arranging to visit there.

Getting to know Dan

Timmy and Dan saw each a lot. Sometimes they’d meet at Mel’s place, sometimes at Connie’s. And it was not always just sex. Dan was really beginning to bond with Timmy, and he’d take him to the zoo, to baseball games — it turned out that both were rabid fans of the same team — and other things that fathers do with sons or uncles with nephews. But — unknown to most of the world — there was a lot of sex between them. Mostly a lot of stroking, playing with each other’s dick, even some sucking, though the difference in heights made 69 rather difficult, so each might suck the other at one point in the session, but not together. Because Timmy’s mouth was still small, he had some trouble really sucking Dan’s cock, so a lot of the time he would just lick around the head, something that Dan actually thought was as stimulating as having the whole of his cock in Timmy’s mouth. Dan never pressured Timmy; they had an understanding that when they were alone together, nothing sexual would happen unless Timmy initiated it. But it was a rare thing for Timmy not to initiate it almost as soon as they got to be alone together. Timmy really enjoyed the sex — when he had a chance, he wasn’t about to forgo it! Connie, of course, understood what was going on between Timmy and Dan, because it was all according to her plan. But she kept up the pretence that she considered Dan as just a friend of Mel’s whose company Timmy enjoyed. And Dan always was polite and friendly to Connie — perhaps, more friendly than Connie and Timmy might have expected, given the relationship. Timmy, of course, was not yet ready to tell Dan about the plan. For one thing, Timmy wasn’t yet sure Dan was the one.

By this time, Mel was sure that Dan was the one Timmy wanted, even if Timmy wasn’t. So he stopped introducing Timmy to new men. It was clear to him that Dan and Timmy were a good match — whenever Timmy and Dan had met at Mel’s place, afterwards Timmy would tell Mel just how great being with Dan was. And Dan had on more than one occasion told Mel he thought he was falling in love with Timmy.

On one of the get-togethers, Dan and Timmy had done just about everything they usually did. Each had jerked off the other simultaneously, and then Dan sucked on Timmy’s little cock while his own body recovered enough so that Timmy could take Dan’s cock into his mouth and give him another orgasm. Dan even had tried putting a lubricated finger up Timmy's hole, stimulating his prostate, something he hadn’t done before. But Timmy had seen a lot of gay porn magazines, so he had some idea of the things that guys do, and he wanted to experience the “ultimate.” So he said to Dan: “Please — I want your cock in my hole.” But Dan said: “I’m pretty big, and your hole is pretty small. If I do it, you’ll get hurt. Perhaps when you’re older.” Timmy responded, “I don’t want to wait years for it!” So Dan said, “Well, there are ways to stretch you so you can take me in you. But you’re not ready now.” When Dan said this, Timmy knew Dan really cared about him and wasn’t just using him as a sex object. And this told Timmy that Dan was the man he was looking for.

The visits became more frequent. It seemed that whenever Dan was not running his business, he was over to see Timmy. And it was clear that both of them enjoyed this, to the point that Timmy didn’t see many of his schoolmates other than in school itself. Neither of the two had much of a social life — it seemed that all the companionship either one of them needed was the other. On Timmy’s eleventh birthday, instead of having a party with lots of other kids, he spent even longer with Dan than his usual get-togethers. And shortly afterwards, Timmy decided that now was the time to tell Dan the whole deal.

The new family

Timmy told Dan about the plan he and his mom had made, about how Connie would marry someone officially, so that Timmy could have an adult male lover in the house without it being advertised to the world. He explained all the points of the plan, and Dan responded: “This would be very hard for me. You see, I’m not just gay, I am what we call bisexual. I am turned on by women and girls, as well as by men and boys. And living in the same house with a beautiful woman like your mother — officially married to her, yet not able to make love to her — that would not be something I could do. I love you, Timmy. But I am also attracted to your mother. And the only way I would marry her is if we made it a real marriage, though, of course, you and I would still have our pleasurable lovemaking as well.”

Timmy was taken aback by this development. He’d never considered things turning out this way. He knew about his uncle being gay, and about most men being straight, but he’d never thought about some guys going “both ways.” He really wanted Dan, but he couldn’t figure out how to have Dan without bringing his mother into a relationship she’d already told him she wasn’t ready for. So the next time he was alone with Connie, he spoke to her about his dilemma. And she responded, “Gee, Dan is really a nice man. And he’s been nice to me too when I’ve met him. I don’t know — maybe, after six years I am ready to marry again, for real. But you will still get to have him in the way we planned, as well. I don’t want to deprive you of the man you wanted so much that things got to this point.”

The next day, Connie called Dan. “Timmy told me about your conversation. I never thought of myself as ready to take a new husband, for real. This was originally just for Timmy’s sake. But I’d like to think about it. First of all, I need to get to know you better. I knew you and Timmy were ‘sleeping together.’ If it seemed to you I didn’t, that was just because you didn’t know the plan, and I didn’t want to make you think I was weird or anything. We need to spend some time together — some of it the three of us, some just you and me. If we’re really going to live as a married couple — lovemaking and all — I need to be sure I’m comfortable with you. And I don’t just mean sexually; I mean in all sorts of other ways. So the next few times you come over, please don’t just pick up Timmy to take him wherever you and he are planning to go. Stay here a while first, so I can learn more about you.”

Dan said, “Fair enough. I don’t know a lot about you either. I think you’re a beautiful woman, as I already told Timmy. And you’re an incredibly loving mother; I can hardly imagine another woman who’d do what you’ve done for Timmy. But that’s all I really know.”

The next time Dan came over, he and Connie talked for several hours. Timmy joined in at times, but he was sure there were things that Dan might feel more comfortable talking about with Timmy not there, so he went away for some of that time “on an errand.” (He’d learned that little trick from his uncle!) Dan explained that while he loved boys, he was really quite bisexual, and the only reason he’d never married, or even dated a lot, was that he had spent the past few years building his contracting business into something where he didn’t have to work seven days a week at it. It was only in the last few months — beginning about the time he first met Timmy — that he really had much time, and instead of dating women, he’d chosen to spend his time with Timmy. He told Connie, “Your son is an amazingly attractive boy, and a boy with a really lovable personality. I’ve grown to love him almost as much as I’m sure you do.”

They agreed that Dan would spend time alone with Timmy as he’d done in the past, but he’d also spend time alone with Connie, and time with the two of them together. And Connie expressed curiosity about the gay relationship Dan and Timmy had developed. While she had a good relationship with her brother, Melvin, she never felt it proper to ask him about what gay people did when they had sex, or anything like that. But she asked Dan whether, since there has now been such sexual openness in their communication, he and Timmy would be open to letting her see what goes on. He responded that Timmy would have to be the one to decide, and when Timmy was asked, he said, “Only if you let me watch when you two are doing it!” Again, Dan said that Connie had to be the one to decide, and she said that, since she asked first for this, she could not in fairness refuse.

So the first time that Connie and Dan had sex, Timmy was in the room watching. Connie felt funny with an “audience,” but of course she still wanted Timmy to have whatever he wanted, and this was certainly something that Timmy wanted. Since Timmy felt strange wearing clothing while the others were as naked as Adam and Eve, he shucked off his clothes too, and moved in to get a better look as Dan penetrated Connie. He actually realized that this turned him on more than he expected — maybe he wasn’t totally gay himself, as he’d thought. After all, he’d decided he was gay before he’d even been aware of bisexual men like Dan. And since that, he was so busy making love to Dan that he hadn’t reassessed what his feelings really were. He got carried away, and started stroking Dan’s balls, which of course made Dan cum sooner than he wanted to, but Connie understood what was going on, and didn’t hold it against Dan. And then Timmy did something that shocked both Connie and Dan after they’d both thought of him as gay. He went over to his mother, after Dan withdrew, and started sucking on one of her nipples. With that, the threesome was complete. Each of them had made sexual contact with both the others.

Once this happened, each one of this threesome realized that they loved both the others — and not just in the mother/son way; they opened up their lives to each other sexually as well. The one who was happiest with this whole arrangement was Dan. He’d always wondered how he — so thoroughly bisexual — could manage to be true to a wife when he had sexual urges involving males as well, or how he could be true to a male lover, as he wanted female sexual contact as well, but with this arrangement, neither his wife — Connie — nor his lover — Timmy — would feel they were being cheated on! Timmy's twelfth birthday was also Dan’s and Connie’s wedding day, on purpose — this was a birthday present for Timmy. The next day, Dan moved in to the house where Connie and Timmy were living. Some of the unused rooms were turned into the new offices of The Daniel Jennings Contracting Company. They agreed that all three would share a bedroom, though Timmy had a room which would be shown as his bedroom whenever a visitor was to be shown around the house. Though Timmy didn’t yet have the ability to have anything but a dry orgasm, he loved putting his dick into all the orifices around on both his mother and his new stepfather. And they were happy to please him. Both the males in this group also used their mouths to great advantage, not only sucking Connie’s nipples but each other’s dicks, as well as lapping her pussy as well. By the time Timmy reached puberty, Connie had decided that if she became pregnant, she’d not do anything to determine the child’s paternity. It could be Timmy’s child or Dan’s, and she’d love it either way. So never was there a thought of contraception. Sometimes, of course, two of the three might have sex without the third, just because they felt like it — there was no need for every sex act to be in a threesome, but it often turned into one, even when it didn’t start off that way.

Of course, all of this was pretty secret, as far as the outside world was concerned. But Connie’s love for both the men in her life, and their love for each other, only grew as the years went on.