Jimmy’s girlfriend Rebecca has been requiring Jimmy to wear a ladies wig when the two of them are having sex, it is her latest turn-on. When Jimmy relays Rebecca’s weird new preference to her best friend Di, she invites him over to discuss the matter.
Di senses that Jimmy really enjoys being feminized and she takes it a step further, offering to apply makeup to Jimmy’s face in order to see how he might look as a female.
When Rebecca unexpectedly stops over to visit Di she finds the two of them in the kitchen. Jimmy is in full makeup and with an immense erection. Jimmy is about to explode with pleasure when Rebecca produces a strange looking device. Its purpose is to encapsulate an erection and prevent orgasm, and it even comes with a lock and key.
Rebecca cons Jimmy into letting her apply the device and then the two girls proceed to fully dress him as a female while his erection gets no relief. And to make matters worse, Becky has hidden the key for the device.