tagTransgender & CrossdressersA Virginal Challenge

A Virginal Challenge


"I keep telling you Jason, no."

"But I've been asking for months!"


"Please? I always wanted to pop someone's cherry!"

"I swear to god-"

"C'mon, Mary, we've been going out for five months now, it's not that big a deal!"

Jason and Mary walk the busy sidewalks of This City at night, having just finished dinner. Mary sighs as Jason continues to plead and beg, while Mary regrets ever telling her 21-year old boyfriend that she, at the age of 30, was still a virgin.

"Jason, stop!" she shouts, spinning to face her boyfriend with an agitated look on her face. "It's my body, I choose what to do with it, and who gets to do it."

"But...I'm experienced! I know my way around the sack, Mary!" Jason cries out, Mary noticing the unusual looks they were getting from passersby.

"The way you're asking right now makes me think that you're not."

"Does it really?"

"Yes!" she shouts at him. "It sounds so desperate, Jason, how do you not see that? It's embarrassing for me, and I can't believe you're not embarrassed for yourself."

"But...I just..." he stammers, trying to find the right words, "the whole time we've dated, I thought you were my age. You look pretty young..." Mary exhales a sigh, annoyed with the remark. While it was true she took good enough care of her skin that she could be mistaken for mid-20's, she felt telling a woman she was "young for her age" was insulting. Still, she lets him continue. "But knowing you're a virgin, it's like...I've always wanted to take someone's virginity."

Mary puckers her lips to the side of her face. She was feeling annoyed that her boyfriend was treating her virginity like it was a trophy. Still, she was very aware that Jason wasn't aware of why she remains a virgin. As she formulates an idea in her mind, she smirks, giving Jason a new attitude.

"Okay," she says, approaching him seductively as she places her hand on his cheek, "you want me? You want to take my virginity?"

"Y-yes!" Jason shouts nervously. "Yes, please! Let me be your first!" He gets down on one knee, his hands raised and folded as he begs.

"Alright, we'll do that. But first, I want to take something from you before you get to take me."

"Name it!"

Mary grabs him by the collar, and leans into his ear as she whispers, "My apartment, tomorrow night. That's when you find out. Bring lube." She lets go of his collar, and smiles wickedly as she sees the excited glow from his wide-open smile.



"Just a second!" Mary shouts as she lights up some candles on her nightstand. She closes her bath robe up, hiding her private parts from plain sight. Looking through the peephole of her apartment door, she sees Jason on the other side, looking as suave as a nervous 21 year old can. She opens the door, and before he can even so much as say "hi", pulls him inside and leads him to her bedroom. "I'm glad you could make it, Jason." she says. "I didn't think you were brave enough."

"Brave enough for sex?" he asks, sweat beading on his forehead. He may have had sex before, but for him it's been a while, and he felt his talking game wasn't strong enough. But he figures tonight it would all be worth it. "I can handle it, Mary." As she stops in her bedroom, his eyes are drawn to the sex swing set up in the middle, Mary's bed shoved against the wall to make room.

"You brought lube, right?" She asks ther nervous boy. He nods ashamedly, holding a little plastic bag for proof. "Well, go on, sit down on it." Mary encourages him.

Jason seems a bit unsure. He thought that the bottom was the one to sit on the swing, not the top. But he does as she asks, and undresses himself before he makes himself comfortable on the swing. "Now...I hope you're ready..." Jason smiles and nods as the swing swivels about, but for how ready he was, he wasn't ready for what Mary had hiding under her robe.

"Is that...is that a dick?!" he asks, jaw dropped in surprise. Mary nods as she strokes the eight-inch long cock attached to her groin, while Jason looks down at his five-incher.

"Real cock, Jason. I'm a hermaphrodite." Mary explains as she shows him her pussy underneath the slab of meat. "My pussy might be a virgin, but I've had so many fucks with this baby." She licks her lips in delight as she strokes herself. "The second every man sees it, they go running out of here without their clothes. And I can see you're about ready to do the same. So here's a deal; if you let me fuck your ass first, because I can tell you're an anal virgin, you get to take my pussy's virginity. Deal?"

Jason wouldn't admit it, but he was very ready to jump out that swing and head for the door, leaving his clothes behind if he had to. On the other hand, if all he had to worry about was his girlfriend's shaft stretching his ass, it would be worth it to take her virginity. Swallowing his pride, he gulps and nods to Mary. She chuckles as she approaches him, stroking her cock as she grabs the bottle of lube from the bag.

"Good, but first we need to work your asshole a little." She pours some lube onto her hands and rubs it onto Jason's little ass, making him wince. Mary then slaps on a medical glove and inserts two fingers inside him, making the younger lad moan.

"M-Mary," he says through a grunt, holding onto the swing chains, "is that necessary?"

"Of course it is. You want the lube to go as deep as possible. You don't want it getting rough inside, do you?

"I-I guess not..." he grunts again, feeling Mary's fingers reach deep enough to hit the prostate. She presses her fingers onto it, watching Jason moan, his eyes shut in ecstasy, as his cock begins to stretch out and harden. His grip on the swing tightens, breathing heavily as he watches his cock stiffen to full erection.

"Aw, look at it. Isn't it cute?" Mary says as she mocks him. "It's not as big as mine, however." She laughs, stroking her cock as she pours lube on top of it. She then spreads it around with her hand wrapped around the dick. Once it's soaked up enough, Mary holds onto a bar holding up the sex swing while holding her cock up, and pushes it in. "Just tell me if it's too much."

"Anh! Slower! Slower!" Jason cries out, clenching his teeth.

Mary nods, gently pushing her way in. Inch by inch her dick goes into Jason's anus, and he begins to feel it rubbing against the prostate. His wrist swing his hands inward on the chains as it massages past the prostate. He could feel her head going beyond that point, but the cock still brushes against him. He yelps when Mary accidentally pushes too hard inside, squirming as he holds back an orgasm. He does, however, squirt out a few drops of precum, which splashes onto his abdomen.

His hermaphrodite girlfriend can't help but chuckle. "Sorry, I forgot to be gentle." she apologizes. "I think we're okay now, Jason. How do you feel?"

"A little stretched..." he says in a higher pitch. "I...I think you can go ahead, but be easy? Please?"

"Just remember those words when you get on me." She winks with a smile as she holds onto the chains near his legs, and pulls them towards her as she rears her hips back. Jason lets out a groan as he hears his ass cheeks slap into her hips, the base of her cock touching his cornhole. "How's that feel?"

"Good, actually..." Jason says after exhaling air from his cheeks. He retains his grip on the swing chains while Mary uses her strength to continuously ram her hard meat into her boyfriend. She watches his dong as it squirts out driplets of precum for each time her cock head rubs into his prostate. Her mouth salivates, wanting a taste of his cum when this is all said and done.

She takes a moment and stops swinging Jason her way. Her hands leave the swing chains and lead to her nipples as she tweaks them between her fingers. "I'm sorry, Jason, I just need to rest a moment. My arms are killing me from all that work."

"It's fine, really." he answers, his hands immediately reaching for his dick. He rubs his palm around his own shaft, licking his lips as he admires Mary's youthful body. "God you're beautiful."

"Think with the right brain, meathead." Mary laughs as she smacks her palm into Jason's ass. "Ready to go again?" He nods, still stroking his cock. "Okay, just remember to hold on tight." She grunts as she grabs a hold of the swing again, and Jason quickly grips his side as she pulls his ass back down on her big rod. Jason looks her in the eyes as she continuously thrusts him into her, the herm cock pressing into his prostate as it slides in and out. He does notice his own erection is dribbling more precum, which splashes around with each push she makes.

"Are you good, Jason?" She asks, still pushing into his ass. "Are you ready to take my pussy's virginity?"

"Y-yeees!" He growls, feeling his cock come close to it's peak.

"Okay, I can tell my fun time is done." The hermaphrodite pushes against the back of Jason's legs as she moves her hips back, the big cock slipping out. The head of the dick makes a pop sound as it makes its escape, and Jason can see Mary herself was dripping with precum. "I wouldn't worry about that." She says with a wave. Mary walks over to her bed and sits back, holding her legs in the air, still stroking her cock. "Are you ready?" She asks as she uses her free hand to slide open her pussy lips.

"Of course, just-ungh!" Jason stands up, only to feel such a pain between his legs that he can barely move right. Mary holds her cock-rubbing hand to her face to stifle a laugh.

"Oh god! I didn't think I did you that hard! She says in an apologetic manner. Jason groans his way slowly over to his girlfriend, and holds her legs up as he rubs his cock against her wet pussy lips.

"It's...okay, Mary...I can do this...maybe not as long as you did..." He grunts through the pain as he sticks his slickened cock head inside Mary, and watches her reaction as he pushes in. Mary's face, no doubt, was very similar to Jason's when she was inside him the first time. Jason thrusts his hips into Mary's ass, pushing harder into her as he felt her pussy loosen. She holds her cock up to his face, suggesting that he licks it. He does so, actually going so far as to suckle on her cock head while he continues his hip thrusts.

Mary grabs her own hair, fighting off the urge to cum. She finds it a bit hard to keep her mind off it, as Jason's tongue swirls on her slit, while his cock rams into her newly spread vagina. She wraps her legs around Jason and flings her upper body off the bed. Still seated, she joins him in licking his own cock, until they both feel the urge to ejaculate swell in their respective cocks.

"Cum in me!" Mary begs, a whimper in her voice. Jason nods, and the two of them shoot their wads out of their meat rods. Mary's herm cock squeezes out a massive load of jizz down Jason's throat, although not without a bit of gurgling. Jason shoots out into Mary's pussy, filling her vaginal cavern up with his semen.

After a loud moan from both parties, Mary grabs her arms around Jason's body, and falls back on the bed. Jason panics as he falls with her, collapsing on top of Mary's luscious breasts. With their eyes wide open, they breathe heavily, amazed at their actions.

"That was exciting, Jason." Mary says, kissing Jason's forehead. "Thank you."

"No...thank you..." Jason purrs as he gropes her breast. "I didn't think I'd like anal so much in my life."

"Well, I'm glad we had this little discovery." She sighs, closing her eyes as they cuddle on the bed.

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