After breaking the kiss, Ty asked, "Eileen..." The feminine name sounded weird to describe this man, but neither of them cared. "How far do you wanna go?"
"As far as you're OK with," Eileen replied instantly.
Ty blushed, and decided to follow through on something he'd considered. He pulled off his T-shirt and shorts, before removing his boxers and lying naked in front of the handsome DILF. "Even this far?" he asked in a small voice.
Eileen got atop him and kissed him passionately again, and Ty took this as a 'yes'. He spread his legs and shivered in anticipation as he felt Eileen's hard, dark cock frotting against his own. Realizing this could get painful, he hastily wished for his ass to comfortably accommodate Eileen's cock.
It was a good thing he thought of that so quickly, as Eileen didn't take long before shoving his cock at Ty's tight pucker and pushing between the cheeks inside him. They both groaned at how the insertion felt, and as Eileen's large dark hands took hold of Ty's hips his own moved to grip Eileen's wrists.
After a few moments locking eyes, Eileen bent down and kissed Ty passionately. Ty kissed back and then moaned as Eileen slowly began to thrust in and out of him, the handsome man's cock pounding against his prostate with practically every thrust.
Ty felt amazed how much he was enjoying having sex with another man. It felt beyond weird to have someone else inside him and the stimulation from getting fucked was so unfamiliar, but he felt so fucking good.
It felt even stranger for Eileen getting to have sex with a man while also being a man himself- the motions of thrusting into someone were so different and getting to be inside someone instead of having them inside her were really different and intoxicating. His hips were soon moving faster and more eagerly.
Before long, both men were reaching their peaks. Eileen clung to Ty and whimpered, "F-fuck... close... gonna~" before shooting a thick load inside him, and Ty felt himself peak shortly afterwards, his cock painting their stomachs with cum as it began to splurt messily thanks to all the stimulation.
Once Ty's orgasm concluded he felt Eileen kiss him again and slowly pull out of him, the continued high of sex and the unusual sensation of leaking cum from his ass so surreal but so nice.
As they recovered from the high, another idea came to them...