Stepmom Makes Him A Man - S14:E9
Jimmy Michaels lacks social skills and is reserved. Though he doesn't have a date and doesn't want to go alone, he is certain that he wants to attend the school dance. Maggie Green, his stepmother, decides to intervene after learning that Jimmy has no intention of leaving. Jimmy is helped off the couch by a curvaceous Maggie, who offers to measure him for a suit so he can look very good. The only drawback is that in order for her to take an accurate fit measurement, Jimmy must undress to his boxer underwear. It's painfully obvious that Jimmy has a massive boner when he complies with his stepmother's request to remove the majority of his clothing. Maggie makes an effort to get around it, but eventually she gives up. She takes off Jimmy's underwear and begins to pet him. Maggie then pushes him back against the wall and takes out her large jugs, allowing him to nurse Mama's enormous tits. Maggie is determined to support Jimmy until he gets his act together, of course, and she won't give up on him just yet. She leads him to the bed, spreads out on it, and begins to lick and caress Jimmy. Jimmy is then invited to have his way with his mother as she reclines. Jimmy can't believe he's getting his dick wet in his stepmom's twat even as he slides on home! To spoon with Maggie, he curls up behind her. Then Jimmy turns over on his back, allowing Maggie to mount him and ride him as if he were her own horse. As Jimmy convinces his stepmother to crawl down on her hands and knees to take Maggie in doggie, he gets another chance to try to grab her. As their scholastic romance comes to an end, Maggie turns over on her back and allows Jimmy carry her home one final time in the missionary role. When Maggie has had enough, she goes down on her knees and sucks Jimmy till he pulls out of her mouth, nutting her face and dripping a come shot down her enormous boobs, leaving them both feeling amazing.