This had been a long time coming, and Ron’s sexual history wasn’t exactly vanilla, but it also wasn’t nearly as kinky as his mind.
As a young man, he hadn’t had a lot of girlfriends, but he had done okay. Most of them had been pretty vanilla, but there was one who he often thought about even now because of things to which she had alluded. He had dated Robin (their similar names made for a lot of dumb jokes by friends) in his 20s, and they had reconnected in their early forties before she met the man who was now her husband. The sex between them was always fun – they were very compatible. Robin wasn’t shy about trying new things and wasn’t afraid to ask, generally. They’d both been single and a chance meeting had led to some sexual flirtation that ended with them back at Ron’s place, with her riding his cock to a mutual orgasm. Neither was interested in dating, but they would get together every other weekend or so (sometimes just for a night, sometimes a whole weekend) and fuck each other’s brains out.
As mentioned, Robin wasn’t strictly vanilla – she didn’t do anything too crazy, but Ron tried things with her that he had never had the opportunity to try before. For example, when they had dated in their 20s, Robin had liked Ron to blindfold her, which eventually led to him tying her down. She then flipped the script and did it to him, usually culminating in an orgasmic 69 when she would coat Ron’s face and tongue with her juices, after which she would kiss him and lick him and taste herself, which always made her horny again.
In her 40s, she still enjoyed that, but shocked Ron when she tied him down and told him, “I’m going to suck you dry and make you kiss me and taste and swallow your own cum!” Ron was at her mercy, which always turned him on, but he wasn’t sure about this – until it happened. And then he wanted to do it again. And again.
But it didn’t stop there – after getting Ron used to that, she upped the ante by riding his dick until he came, then quickly moving to sit on his face and make him clean his cum out of her. This would always result in her having an explosive orgasm before she kissed and licked his face clean of their mixed juices.
It seemed that the more kinky things they did, the kinkier Robin wanted to get, and Ron was usually open to at least a discussion or a fantasy even if he didn’t necessarily want to do those things. Occasionally, she would talk about things like having sex on a nude beach or somewhere they were bound to be seen and watched by horny passersby. She often talked about going to a swinger’s club and watching him with someone else, or how she would like to masturbate in front of a room of men and women and know they were getting off on watching her. She’d tease him with talk of a threesome with another woman and how she would make him beg them to be included. She’d talk about bringing in another guy, fucking him, making him cum, and then Ron getting sloppy seconds and how horny that would make her and what massive orgasms she would have. Further and further each time – and Ron ate it up. He loved it.
He encouraged it, and they eventually talked about it seriously.
When they talked about who they would “invite” Robin first suggested inviting her bisexual male friend, James, joking that, if she was tired, James could “help” Ron out and would probably even like to let Ron fuck him. Robin always played it as a joke, saying things like, “You know, if you want to try anal, James is available” but she mentioned inviting him often enough that Ron knew that it wasn’t just a joke, and she eventually admitted that, when Ron and James had met, James had confided in her that he found himself very attracted to Ron. He’d even told Robin that he would “gladly” let Ron use him “as his personal sex toy”.
“He wants to fuck you and then let you fuck him,” Robin offered, a sexy smile coming across her face as she said it.
Seeing that it turned her on, Ron started to incorporate it in their sex lives, asking her, “Would you like it if I fucked your pussy while James licked you?” or “I’d make you both suck me and then I would cum on both your faces” and, in turn, Robin would do things like tie him down, blindfold and say things like, “Imagine I quietly brought James in here now and let him suck your cock while I watch. Imagine my tongue is his tongue and he wants you to fill his mouth with your cum. Oh my god, it would be so fucking hot to watch him suck your cock and see you cum down his throat!”
The more they fantasized about it, the more Ron started to want it to happen, though he struggled with admitting it to himself, let alone her. And after Robin eventually confessed during one particularly energetic and raunchy session that she really wanted to watch him and another guy in a 69, Ron started fantasizing about that and finding himself almost desperate to find out what it was like to be with a man. The more he thought about that, the closer he got to finally admitting to his curiosity and telling her to invite James.
As fate would have it, though, Robin met her husband-to-be before Ron could muster up the courage, and their hook-ups very suddenly stopped, leaving Ron alone with these frequent wild fantasies and the question in his mind of whether he would like it or not.
With Robin no longer satisfying his sexual urges, and no girlfriends on the horizon, he was left to masturbate to alleviate his needs. At first, the fantasies and images were normal but, gradually, he started gravitating to kinkier or bisexual porn. Seeing a supposed husband and wife seducing another guy made him start thinking of her and James seducing him – leading him because he was too nervous. Robin would be kissing him and stripping his clothes off before pushing him back on the bed, and while she kissed him and nibbled on his neck, he would feel James starting to lick his balls and squeezing his dick. These fantasies would never get too far before he would cum, but, for a few days, they would satisfy his growing curiosity.
Eventually, though, that all changed. He had woken up “extra” horny this day and couldn’t get the fantasy out of his head. As he let it play out, going further than usual, he imagined Robin telling him that she would have a threesome with a woman, doing anything Ron wanted, if he would go down on James.
“But you have to make him cum in your mouth,” she would insist.
Ron let himself imagine anything and soon, in his mind, he could see James lying naked on the bed. His 7-inch uncircumcised cock standing at full attention, and a look of hopeful anticipation on James’ face. Ron knew he would start by caressing James’ body with his fingers, his eyes intently locked on James’ rigid but twitching dick. As he watched it, Ron would move his hand down to grab it and squeeze it, feeling its firmness. James, so turned on, would reach up to grab Ron’s face and pull him down to him, kissing him deeply and passionately. Ron would not only feel his own hard on begging for some relief but would also feel James’ cock somehow feeling even harder in his fist. As he would start to move his hand up and down, slowly stroking James, who would fall back as he reveled in the experience of being Ron’s first, Ron would feel an urge to lean over and swallow James’ dick and make him gasp with pleasure.
Then, as if giving him permission, he would hear Robin say, “Suck him for me,” as she started furiously rubbing her clit, her eyes locked on what Ron was doing,
“God, yes, I need to feel your mouth on my cock. Please,” James would beg and Ron, his desire growing by the second, would loosen his grip on James’ cock and slide his fist up to the head and let James’ leaking precum dribble over his fingers. Staring at Robin, he would bring his hand to his mouth to taste James for the first time. As he licked his fingers clean, his eyes locked on Robin’s, he would watch her spasm violently as her fist orgasm shook her body.
Leaning over now, he would let his tongue circle the top of James’ cock, tasting more of him as Robin watched.
“Fuuuuuuckkk, please, please, suck me, please. I need to feel your mouth. Please,” James would beg before Ron finally opened wide and leaned forward to take as much of James’ cock in his mouth as he could. He’d start slowly, wanting to build up to something great, but also wanting to tease James a bit. James, though, would have other ideas.
Ron imagined James’ hands reaching to grab the sides of his head, saying, “I’ve dreamt of fucking your mouth” before forcefully rolling Ron over onto his back. James, now straddling Ron would move up Ron’s body and lean forward, his arms holding him up, his cock now right at Ron’s lips before starting to buck his hips, forcing his cock as deep into Ron’s mouth as it would go. Faster and faster his hips would move as he thrust in and out of Ron’s mouth. Ron imagined his own cock spasming as precum leaked heavily from it.
James would then move Ron into a half-sitting position against the headboard before kneeling in front of him, grabbing both sides of his head and thrusting his cock forward. Ron would instinctively open his mouth to welcome James’ delicious cock and reach his hands around to grab James’ tight ass as James would start pistoning his cock in and out of Ron’s mouth.
Ron imagined Robin having one noisy, incredible orgasm after another as she watched Ron tighten his mouth around James’ cock as James pumped ever faster, arching his back, looking up to the ceiling as he furiously fucked Ron’s mouth.
“God, I’m going to cum,” James would cry, and Ron, now desperate for the reward that he knew would be splashing onto his tongue and down his throat, simply mumbled his hungry response.
“Mm-hmm!”
“Oh god, this is so hot! Cum in his mouth! Make him swallow your cum!”
Ron imagined a sudden torrent of cum hitting the back of his throat, filling his mouth as James let out a guttural roar of passion. Ron would not be able to swallow it all and he would feel some escaping the corners of his mouth but, while James had now stopped pumping, Ron would continue to suck James’s cum covered cock until he had sucked back all of Ron’s cum.
With a grunt, he started to cum, ropes of it shooting up above him, landing on his chest and stomach and on his hand that still was tightly gripping his cock. Wave after wave of orgasm rocked his body as he imagined cum shooting into his throat as the fantasy James let out a guttural roar and bucked his hips, pushing his pulsing cock as deep into Ron’s mouth as possible one more time.
What had Robin done to him?