Author’s note: This is the first official re-write of the Wingman series. Originally written in 2012, this particular piece is the only one that will be a simple re-write of an episode from the first set. Due to Wingman now being part of the Infinite Monkey universe, the overall story arc will change significantly from the earlier set.
“Are you cross?”
Cross allowed a slight glare. “That was not funny the first time you used it.”
Prince Steffan laughed and slapped his shoulder. “Yes, I need new jokes, Cross. This is for certain. Perhaps I should order you to write them for me.”
Standing at attention, Cross held his mouth shut. The fear that Steffan might command him to write jokes was real.
He placed his helm on the hook and began to take off his armor. “I need you to keep lookout tonight,” the prince looked up at Cross. “Lady Angelica will be visiting tonight before she is off to her wedding.”
“I see, sir.”
“You will need to keep watch and escort her to her waiting carriage after we are finished.”
“Are we certain the carriage will be waiting, sir? The last time…”
Steffan picked up his goblet of wine and gulped. The wine flowed over his lips and trailed along his muscled neck to soak into his undergarments. For a moment he stood, armored only from the waist down. “It will be there, Cross.”
Trying not to laugh, Cross put away the armor that Steffan had dropped on the stone floor. He spoke no words, waiting for the prince to continue.
Loving his own voice, Steffan did just that, “She’ll be here within the hour. We need to have her out your entrance by the time the clock strikes eleven. I’ll also be needing you to watch the clock for me.”
“Yes sir.” Cross tried not rolling his eyes. He hoped he succeeded.
After a wash, Steffan stood gazing into the mirror. A quick adjustment of his red silk ascot, tucking it into the collar of the black shirt. The same shirt that was tight enough to show off his muscles. He whistled at himself. Tonight he planned on playing gigolo. Tight clothing, slick black hair in a ponytail, and eyes the blue of Nottingham’s skies…what woman could resist?
His playmate for the evening, Lady Angelica, arrived in a black cloak with her hood pulled up to conceal her face. One of the maids led her into the room.
Angelica and Steffan exchanged quick pleasantries before Cross was handed her cloak. They had a few drinks whilst sharing laughs seated on the bed. It was not much longer and Cross was picking their clothes off the floor around the bed as their bodies writhed and penetrated on top of it.
Candlelight accepted the responsibility as sunlight gave up on its daily effort.
The took turns with mouths on gonads and frolicking through the evening. Cross sat in silence, fighting to stay awake. They may have been a gorgeous couple, but this was not his first time watching Steffan’s play. Finally, the time came for him to speak, “Sir, madam. Your time is at an end.”
In the most quiet voice she used that evening she whispered into Steffan’s ear, “Your eunuch shouldn’t be giving us orders, should he?”
“It’s okay, I told him to keep an eye on the clock for us. We’d be lost without him.” Steffan gave one last kiss to each of her breasts. Climbing up on his knees, he pushed his cock into her mouth one last time until his semen dripped along her cheek again.
After wiping the last cum from her lips, she dressed. She then followed Cross out through servant tunnels to her waiting coach. Cross did not mention how relieved he was to actually see a coach waiting as instructed, this time. He retraced his steps and found Steffan near sleep on the bed.
“Is she gone?”
“Yes, sir.” Cross answered and filled his own goblet of what little red wine the couple had left in the bottle. “One of these times, your schemes are going to fail. I’m scared to think how many little Steffans are running around thinking they are actual royalty.”
“She’s gone, Cross…no more sirs tonight. Just Steff. And, you’re right…hopefully I’ll not meet a little unexpected Steffan-in-waiting some day.”
Cross sipped his wine and helped him pull up his sheets. “Go to sleep, Steff.”
Steff answered with an inebriated snore.
“Besides,” he whispered. “Who the fuck told her I was a eunuch?”
“I owe you, Cross,” he said in a muffled slumber voice.
“Of course you do, sir.” Cross put out the remaining candles with my wet fingers. “And you’ll never repay that debt.”