'Ready for anal?' Jessie asked in a pleading voice.
'It's ok. Just relax.'
Jessie layed down beside him on his back. He grabbed Simon's arms and pulled him on top of him. His back was touching Jessie's hard chest. He could feel Jessie's hard dick on his left but cheek as he started massaging his virgin hole.
'Mmm. Feels good Jessie.' He couldn't help blurting it aloud. Jessie reached over grabbing the lube under the pillow.
'Now this is probably going to sting a little.' Jessie told Simon matter-of-factly. He lubed up his fingers and stuck his index finger up Simon's tight ass. He moaned a little. He switched to two fingers, and then three, getting him warmed up for a good old fashion banging.
They stayed in that same position as Jessie maneuvered Simon to get his smooth thick uncut cock in him. First, he lubed up his cock and ass. He sat it on the edge adding more pressure.
Before putting it he said, 'Remember this is going to hurt. But it's going to fill you up nice and full. You will be begging me to pound you harder and harder until we both cum.'
He kept adding more and more pressure until it went in with a loud pop. Then Simon groaned 'ahahahah. You're big.'
'I know. Just relax and lean on me. It'll get better.' Simon obeyed rewarded with a kiss on his neck by Jessie. 'I promise.'
After a minute or two of loving his neck Jessie asked, 'Feel better now?'
'Uh huh. You can go in deeper now.' He slowly inched his cock in deeper and deeper enjoying Simon moaning in pleasurable pain. Then he pulled it almost out then rammed it all the way in his ass, using a quick hard jab.
'ahhhhhh. Oh god..... ahhh. Fuck!!'
His entire hard thick nine-inch cock was touching his prostate. He stroked it in and out
Using repeated well-timed strokes. They both came at the same time in no time. When they were done Jessie licked the cum off Simon's chest.
'Your cum tastes so good.' He smiled adding, 'Not as good as mine but good.'
Simon playfully smacked his first lover on the face. Jessie kissed the soft spot on his wrist. They cuddled with Jessie's arms around Simon's body. Simon loved how warm Jessie's chest felt.
They fell asleep waking up around 2:00pm. Simon put on his clothes. Jessie lying naked in bed revealing his hard naturally tanned skin. His body was hairless Except for a little under his belly button trailing to his trimmed pelvis. His dick and balls were as smooth as Simon's back.
'When you comin back?' Jessie asked his eyes pleading for his return.
'Maybe tomorrow... If that's k,' he added.
'fine.' Simon left to go freshen up and finish the rest of his day. He would come back to Jessie tomorrow. to be continued......