Helena Macneil: a Femdom Story
Copyright© 2025 by JohnMurray4173
Chapter 2: How It All Began
Erotica Sex Story: Chapter 2: How It All Began - The story of FemDom Mistress Helena MacNeil, who first came to our attention in my story Slut Babysitter: MILF Hunter, and her sissy husband Brian Parker. It details how a young Helena learned her roll as a FemDom and how she chose Brian to be her husband and then broke, subjugated, and sissified him to make him what she needed him to be. It tells of Brian's resistance to Helena's demands and how he broke and learned to enjoy being Helena's cocksucking sissy boy.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa mt/ft Ma/ft mt/Fa Fa/Fa Fa/ft Ma/Ma Teenagers Coercion Consensual Reluctant Slavery Gay Lesbian BiSexual Heterosexual CrossDressing Fiction Cheating Cuckold Wife Watching Wimp Husband Incest Mother Son Brother Sister Father Daughter Niece Aunt Nephew BDSM DomSub Humiliation Light Bond Sadistic Spanking Torture Group Sex Orgy Anal Sex Analingus Cream Pie Facial Fisting Oral Sex Pegging Sex Toys Squirting
“Helena, I am telling you that you’re not going out on a date with that boy!” Taylor MacNeil told his eighteen-year-old daughter.
“And I’m telling you that I don’t care what you say!” Helena reposited. “I’m eighteen-years-old and I can decide who I’ll date and when!”
“Not whilst you live under my roof and accept my money so you can go to university!”
“Then you can stick your house and your money up your arse, daddy dearest! I’ll pack my shit up and move out tomorrow!”
Helena grabbed her purse and ran out of the house, getting in her boyfriend’s car.
“Is everything okay?” Matt, her current boyfriend, asked.
“Just my dad being his usual asshole self. I’m done here, and I’ll have to bring forward when I planned to leave. As you know, I planned to enter the dorms at UQ (University of Queensland) when I start uni next year. But Dad’s becoming more and more unreasonable, so I’ll need somewhere to stay until uni starts in February. It’s just as well that I have my data entry job for the summer because it means I can afford to stay with my sister, Janey, at her unit until the dorms open.”
“What do you want to do tonight?”
“You’re hoping to get lucky tonight, huh?”
“I’ve been very patient and have done what you’ve asked, so, yeah. Right?”
“You’re ready to let me dress you up in my panties, tie you to your bed, and fuck your ass with my strap-on?” Helena confirmed.
“I’ve shaven all my body hair off, and I’ve been moisturising my face and around my groin like you asked.”
“Then you can have me after I’ve fucked you to orgasm several times,” Helena said, smiling.
“Do you really think that fucking me in the ass with your strap-on will make me cum?”
“You love it when I finger your prostate as I blow you, so yeah. I think you’ll cum. More than once or even twice, I’d bet.”
Helena was doing an admirable job of hiding it, but the reality was that she was terrified. Matt was the first boyfriend she’d had who hadn’t totally freaked out when she stuck her finger in his ass. But Helena was determined to be different from her mother, and not a doormat for her future husband.
“What’s with making me shave my body hair off and making me wear your panties while you fuck me? Are you sure you’re not a lesbian or something?”
“You know that I’ve had sex with several women, Matt. But I’m not a lesbian. Bisexual? Definitely! But I’m definitely not a lesbian. But it is true that if we fuck tonight, you’ll be the first man I’ve had inside me.”
“You’re a virgin?” Matt gasped.
Helena shook her head. “Not really. I’ve had tongues and fingers inside me, and my first lover fucked me with her strap-on. I think that qualifies as sex, doesn’t it?”
“But I’ll be the first real dick inside you?”
“You’re not a dick, Matt!” Helena teased. Matt laughed, and Helena continued, “You’ll be the first man to stick his cock in me. I’m looking forward to it.”
The couple had a light dinner, along with a glass of wine each, before heading to Matt’s unit. They indulged in the usual makeout session that preludes sex, and then Helena instructed Matt to strip and kneel with his forehead on the ground, his panty-covered ass up in the air, and his fingers holding his ass cheeks apart so his rosebud was displayed. Once he was in position, Helena moved his thong panty aside and eased her lube-covered finger into Matt’s ass. She followed that with a second and third finger, stretching his ass until she was sure it would accept her ‘cock’.
“Get up on the bed,” Helena said breathlessly. Her whole body trembled with anticipation and excitement. She was going to do this—peg her first male. ‘It’s a shame he wouldn’t let me feminise him entirely,’ she thought as she tied Matt’s wrists to the headboard.
Matt’s ankles followed, with Helena handcuffing Matt’s left ankle to his left wrist and then repeating with his right. This left Matt naked except for his thong, and exposed his taut ass and gaping asshole to Helena’s excited gaze.
Helena, panting with excitement, knelt with her thighs on either side of Matt’s ass. She held her strap-on in her right hand and balanced by using her left on Matt’s upturned legs. After shuffling forward, Helena centred her ‘cock’ in the middle of her boyfriend’s dark star and gently eased it inside.
“Oomph,” Matt grunted as his knot opened and allowed his girlfriend’s ‘dick’ into his ass.
It took a few strokes before Helena worked out how to fuck her boyfriend’s ass successfully, but she soon gained a powerful rhythm that had Matt gasping for more. Helena, perhaps fortuitously because it was her first time, had gotten her penetration angle exactly right and had the tip of her strap-on scraping across Matt’s prostate, his P-spot, with every inward stroke. That alone had the young man climbing towards an orgasm, so when Helena gripped his rigidly erect cock and began jacking him simultaneously, Matt’s resistance almost immediately crumbled. Matt’s body spasmed, then he groaned and spat globules of cum from his straining cock.
The first spits flew into the air and fell onto Matt’s chest, but then Helena redirected them, and the next one spurted into Matt’s open mouth. “Yuck!” He yelled, trying to spit it out. Unfortunately for him, Helena found the sight of him eating his own cum sexually exciting, and she began gathering his spend from his belly and chest and trying to feed it to him.
“Yuck! What the fuck are you trying to do?” Matt objected.
“Open up and swallow, bitch!” Helena hissed, grabbing Matt’s balls.
“No!” Matt protested.
“Yes!” Helena demanded, squeezing her boyfriend’s balls.
“Ouch!” Matt yelped, which gave Helena a chance to feed some of Matt’s gathered cum into his mouth.
He tried to spit it out, but Helena squeezed his balls again and demanded, “Swallow or I’ll rip these off!” She tweaked Matt’s balls again.
Matt reluctantly closed his eyes and mouth before grimacing and swallowing. He’d no sooner gulped the first lot down than Helena twisted his balls again and fed him more cum when he opened his mouth to yelp. Matt protested, but the problem with his complaints, as Helena discovered, was that his erection suddenly roared back to life. His cock rolled, straightened, and then inflated to full erectness.
Helena, laughing at Matt’s discomfiture, re-introduced her ‘cock’ to his asshole and began fucking him as she jacked him again. Despite Matt’s protestations, it was less than five minutes before his prostate clenched around Helena’s strap-on, and he ejaculated cum into the air. As it had before, most of it pooled on Matt’s chest and stomach, and using her ball-squeezing technique, Helena gathered it up on her fingers before feeding it to him.
Matt demanded to be released, but Helena was having too much fun. She felt powerful and dominant, a feeling denied to by her overbearing father and submissive mother. Helena wanted that feeling to continue, but recalcitrantly, Matt’s cock refused to rise to the occasion again. In desperation, Helena eased her finger into his ass and stroked his P-spot as she took his cock into her mouth. That did the trick, and Matt was soon moaning appreciatively instead of protestingly.
The twin assaults on his erogenous zones crashed Matt into a third orgasm in less than thirty minutes, something that even teenage boys find challenging. However, Matt’s torment wasn’t over because Helena had held his latest ejaculation in her mouth. Looming over him, she grabbed his ball sack again, kissed him, and tried to feed his cum that she’d held in her mouth back to him. It took a hefty squeeze on Mat’s balls before he allowed Helena to feed it to him.
Satisfied with her work, Helena stepped off the bed and examined her boyfriend. She realised that making him eat his cum and forcing erections on him excited her. Helena thought that if he’d agree to feminise further, her attraction would soar, but she found his reluctance to do as she wanted and eat his cum irritating. She thought he should submit to her desires more readily and without so much whining. Helena discovered that dominating Matt was extremely exciting, and her clit throbbed as she remembered what she’d made him do. She stood looking at him, considering what to do about her throbbing clit and soaking pussy.
“I want to ride you,” she told him. “But only if you agree to slide down the bed and let me retie you.”
“No fucking way, you bitch!” Matt yelled. “You’re a fucking freak! I’m not some faggot that wants to eat cum!”
“But I’m expected to kiss you after you’ve used your tongue on me? Fuck you, buster. What’s sauce for the goose is sauce for the gander!”
Helena studied Matt until an idea formed: She could easily pull his cock forward so it stuck out behind his thighs, and if it was like that, she could squat outside his hips and lower her pussy onto his cock. All she had to do was get him hard again. She climbed back on the bed, and by using her mouth on his cock and her finger in his ass, returned his dick to rigidity, despite Matt’s objections.
After taking her strap-on off, Helena pulled Matt’s cock down until she could position it at her entrance. Then, relaxing her slender thighs, she lowered herself onto it, balancing on her hands, which were wrapped around his ankles. Helena sighed, enjoying having a flesh cock inside her for the first time. She’d need this regularly; she knew that now. But it would only ever be on her terms and with her in control.
That meant, unfortunately, that Matt had to go. He fought her too hard and resisted what she wanted for too long. But it would be a balancing act. She effectively preferred women to men, but needed a real live cock to truly satisfy her, and there was where the trouble would be. Could she find a woman partner who could accept her need for cock, or would she be better to subjugate a man and make him her bitch, therefore allowing her to have sex with other women?
And other men, too, she suddenly realised. If she went down that track, she would have a suitable rich male partner who would provide for her and their children, but he would be her bitch and have to accept her fucking whomever she wanted. It was time to start looking for that man, and Matt wasn’t him.
Helena suddenly realised that she’d fallen from the cusp of her orgasm and was now seriously behind Matt on the climb to their peaks. She refocused and thought of how she’d spent close to an hour dominating and using him for her pleasure. Those thoughts sent her back to her orgasm’s precipice, and then feeling Matt’s solid, but mediocre-length cock filling her pussy with whatever he had left, tossed her off that cliff, and she enjoyed a petite but satisfying climax. More because of how she got there than the act itself.
After her orgasm passed, Helena considered what to do next. She knew Matt was angry at her, and it was quite possible that he’d turn violent when she released him from his restraints. However, because she didn’t see a future with him, Helena thought of one last thing she could do to get herself off and humiliate him in the process.
After retrieving a piece of soft rope from her bag, Helena tied it around Matt’s balls. She pulled on it experimentally, eliciting an anguished gasp of “No!” from her man. Helena then held the rope at its end and positioned herself until she could lower her cum-filled pussy onto Matt’s face. She hesitated above his horrified eyes before growling, “I’m going to lower my cunt onto your face, and you’re going to eat your cum out of it until you make me cum. If you refuse, try to bite me, or do anything other than eat my pussy, I will rip your balls off! Are we clear?” Helena hauled on the rope to emphasise her point.
“I’m going to slap you stupid once you release me,” Matt threatened.
“I guess that means you’re staying tied up until someone finds you, doesn’t it?” Helena chuckled before hauling on Matt’s balls as a warning and lowering her cum-messy pussy onto his lips. It took another painful tug before Matt opened his mouth and used his tongue to clean his semen from Helena’s vulva. Helena crested twice as he ate her, but those minor orgasms were more from the act of dominating him than his expertise at licking her.
Unfortunately for the young man, his body betrayed him, and by the time Helena climbed off him, Matt had another raging erection. Fascinated, Helena dragged on the rope, abusing Matt’s balls as she stroked his shaft. The combination of pain and pleasure proved too much for the teenager, and with a despairing groan, he shot his cum into the air again.
Leaving Matt tied to the bed, Helena dressed, loosened the ties enough that he should be able to escape, and left. She had a lot to think about. Matt’s sexual response to Helena’s abuse fascinated her, and her pussy heated and got wet as she thought about doing something similar to that again.
Matt sent several messages and attempted to call her as she drove home, but Helena ignored them all until she got home. Her father tried to restart their argument, but Helena ignored him and her pleading mother, packed as much of her stuff as she could, returned to her car, and drove to her sister’s place. She never set foot in the family home again.
After checking in with her sister that she could stay until the uni dorms opened, Helena went to the spare bed to reflect on her encounter with Matt. She understood that the actual act of making love to him had done nothing for her libido at all. However, dominating him and torturing his balls excited Helena enormously, and she knew what she wanted from her men. She wanted them subjugated, feminised, and prepared to serve her wants and needs. She knew if she picked and trained them correctly, they would do all of that for the mere chance of her allowing them an orgasm.
It wasn’t until the following morning that Helena checked her phone. To her surprise, the messages were all from Matt begging her to come back and play with him some more. Of course, she suspected he hoped to get her alone and then return the favour. i.e., tying her up and torturing her whilst using her body to get off. Helena chose to let Matt stew for a week before she warily phoned him and asked what he wanted.
“I want more of what we did,” Matt said enthusiastically. “I’ve been masturbating non-stop, remembering what we did. OMG! I came like five times in less than two hours. I haven’t done that before, even when I was at my horniest.”
“You mean you masturbated five times in a row thinking about me dominating you? Or you came five times while I had you tied up?”
“Well, both.” The embarrassment was obvious in his voice.
“You seriously expect me to believe, after the names you called me and the threats you made when I had you tied up, that you want me to do it to you again?”
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