Astolfo's Legend! "Orlando Innamaroto"

Astolfo sat upon his horse and put on his helmet. His slender feminine body hidden beneath his gold and pearl covered armor. He prepared his lance against his opponent. The mighty knight and prince of Cathay, Argalia. He was a mighty and dangerous opponent, but that was part of the fun.

The night before, he had arrived with his sister Angelica and four imposing giants at the court of Charlemagne during the great feast of Pentecost. Angelica's beauty had stunned the whole court. She was tall blonde, and voluptuous. As they were from an enemy kingdom, they proposed to the knights, that whosoever could best him in a joust, would receive her hand in marriage. Losers, consented to be bound and taken prisoner back to Cathay. Every night including Astolfo and his cousin Roland wanted to face off against him and win her over. The rabble started to irritate Charlemagne, so he ordered a raffle to be drawn. The lucky winner to go first, was Astolfo.

He stepped on to the field and met with his target. He gave him a smile of determination. He was confident in his abilities, as a knight and as warrior. "Hope your ready! Cuz I'm comin' at ya hot!" He was struck down almost immediately. The impact of the lance sent him flying into the air almost doing a full flip. He fell down upon the ground hard on his backside. Some knights, laughed, others cringed. The knight tried to stand but had trouble, as the impact made him dizzy. Once he had finally gained composure he shouted out in protest. "No fair! The sun was in my eyes! He got lucky!" But to no avail, nobody cared to give him a second chance. As disappointed as he was, he didn't fight it, and he accepted the results.

"Oh well." He shrugged. "I guess it just wasn't meant to be!" He smiled and dusted himself off, accepting the results. He looked up at Angelica and said to her. "Sorry my lady, guess I wont get to be your husband after all." He waved at her laughing embarrassingly while winking. He didn't really like the idea of winning her over that way anyway. He was really more in it for the fun of it. Angelica's heart had skipped a beat. The handsome knight was just too cute in his own funny way. "Welp guess I'll go back to the crowd and watch the rest of the tourna-" He was interupted by Argalia. "Hold it right there Paladin of Charlemagne! We had a deal, and you lost, that means you are now property of Cathay!" "Ehehehe... a deals a deal I guess!" Astolfo was then forcefully bound by two of the giants employed by the siblings and carried off to a nearby encampment. Seeing him being treated so roughly deeply hurt Angelica. He seemed like such a nice fellow.

They were going to throw him into a cage to be transported back to Cathay at the end of the jousts, but Angelica intervened just before the giants had a chance to throw him in. "Stop this at once!" She shouted. "Put him down this instant!" You are Astolfo, yes? You are a prisoner of your own consent aren't you? You agreed to this! So these ropes are unnecessary yes?" "Of course! I gave my word! So no matter how unpleasant it is, I'll put up with it!" He answered back with an innocent smile. His chivalric sense of honor, yet playful attitude was so charming, and now being up close to him. She could tell he was even more handsome then before. His beauty was so great, that within the right clothes, he could easily be mistaken for a woman. "I see, well, since there is no risk of you attempting to flee, then perhaps we can house you somewhere more comfortable..."

She untied him and led him to her personal tent which had a lovely plush bed on the inside. "Wow! This place is so big and nice! It's like you got a whole castle bedroom on the go!" He gleefully shouted. She put out of a set of clothes for him to change into and smiled. She needed to get back to the matches, her brother's next match should be starting soon against the allied Muslim knight of Charlemagne's, Ferrau. But she was having to much fun showing Astolfo her temporary abode. When she turned her head back to him, she was surprised to watch him removing his armor and revealing his slender physique. He was even more beautiful then she realized. A bizarre yet wonderful mix of feminine and masculine. His body had well defined muscles from years of training and battling.

"He wasn't getting fully nude, just removing the large and clunky armor that he wore over his tights. He soon got into the comfortable plush robes that Angelica had offered to him. He leaped into the bed and sighed in relief. "Ahhh.. Much better! My armors good and all, but I wish there was something more breezy I could wear on the inside!" She sat next to him. She tried to tell him that she had to go, but ended up listening to him prattle on about his ludicrous stunts and adventures. Before she knew it, it had been nearly an hour. "I'm sorry, I have to getting going." She tried to stand up, but Astolfo grabbed her by the hand. "Are you sure? You don't really seem like you really wanna be there." "I-I need to support my brother..." She was clearly flustered and enamored with him. He took this as his invitation.

He leaned in and kissed her on the lips, she quickly gave in and reciprocated. They stayed like this for awhile, and soon the femboy began to pull at her dress, slowly removing it. He exited the kiss to begin licking her nipples in little swirls with his tongue. Angelica's bosom heaved as she breathed deeply, her fingers running though his soft pink hair, which smelled of strawberries. His fingers moved down to gently caress her warmth before sticking them inside. She knew she shouldn't be doing this. She needed to be pure, in case she actually did receive a husband tonight. But he was so charming and seductive. He no longer had the face of a cutsey airhead, but one of a cutsey, dominant, womanizer. She could not resist him.

After fingering her for a few minutes, he got up to remove his tights. It was then she discovered the cause for his discomfort earlier. Out of his pants popped out his massive, fully erect cock. The size was absolutely incredible. Never had she seen or heard of someone having a penis as big as his. It measured roughly nine inches long! He teased at her entrance with it. "Guess my lance will get a second chance after all..." He slowly pushed and penetrated his way into her. His femboy cock sank slowly all the way down to the hilt. He then slowly pulled out and repeated this process. Astolfo fucked Angelica, gently at first, but slowly picked up the speed and got rougher with her. She held her mouth closed, desperately trying to prevent herself from moaning in ecstasy and being discovered. Astolfo had a smug face as he stared at his lover on the verge of losing it. "C'mon Angie, you gotta get a hold of yourself, if we get caught, it'll be bad for both of us! Unless that kinda thing excites you?" His remarks drove her over the edge. Orgasm rippled through her body. Her voice barely contained. If Astolfo was nervous, he didn't show it.

He still wasn't finished with her. He kept fucking her harder, increasing his pace and speed. "That's it Angie, I'm gonna cum...ooohhh yeeaaahhh..." He flooded her insides with his femboy cum. So much so that it leaked out of her like a waterfall. He slowly pulled himself out, both of them enjoying the final feeling while leaking more cum on to the floor. "Hah! That was nice!" He sighed and exclaimed. The airhead had returned, and the womanizer was gone. He relaxed on the bed and soon completely passed out, his erect cock still dripping semen. Leaving Angelica, a cum stained happy mess.