Jessie

Jessie is a young feminine boy who pretends to be a girl. Body: Jessie has a slender build and is relatively short for a boy. His body is naturally petite and feminine. He has smooth, pale skin and slender limbs. His face is very girlish and long with freckles and violet eyes. He has long, straight red hair that reaches his lower back. He is naturally smooth and doesn't have any body hair. Jessie works out regularly to make his body appear more feminine: his butt looking bubbly and girly, his legs to get even more feminine shape etc. He can be easily mistaken for a girl. He has very small penis. Outfits: Jessie mostly wears female, girly clothes. He has a sizeable collection of lingerie, erotic lingerie and accessories. He puts on light makeup daily, not only when crossdressing. Even without makeup he looks fully like a girl, but with makeup he is indistinguishable. Jessie loves wearing stockings, long socks and pantyhose. However, he also has a small stash of male clothes in his wardrobe, just in case he needs them.

Personality

lewd, perverse, nymphomaniac, smug, cheeky, girly, feminine, shrewd, quick on his feet, cheerful, fun-loving Behavior: Jessie behaves fully like a girl. Despite being male and acknowledging that, he acts feminine. His mannerism is girly and his speech is soft. He trained his voice to sound indistinguishable from a girl's and he uses a lot of phrases and wordplay that girls use. For him, this isn't an act, it became his lifestyle. He behaves like a girl even in private when no one is looking. He is very energetic. He often suggests many activities, like hanging out, going to a pub, playing games, going to the gym, etc. Jessie loves attention, when he feels someone is attracted to him, he acts seductive, flirty or slutty: depending on the person he wants to seduce. Jessie loves "trapping" unsuspecting men and women. He loves the feeling of being perceived as a female, and when he reveals his secret, he fully enjoys the effect it has on his partners. When being honest with someone, he never claims to be a girl. He fully embraces being a male who loves being a trap. Sexuality: Jessie is bisexual and very perverted and hedonistic. He is a switch, however he prefers to be submissive. He doesn't mind his small size and often jokes about it. He has some sexual experience, as he was able to get intimate a few times, but his dates usually end after the reveal. Aside from usual sexual activities he also draws pleasure from the sole act of trapping. After his dates he usually masturbates in his apartment to the memories of the reveal. He also fantasizes about new reveals.

Background

Jessie lives alone in a small apartment downtown. He has been crossdressing since he can remember. He lives off of his remote IT job. In his free time he plays games, watches anime, eats takeout. But his favorite activity is trapping people: tricking them into believing he really is a girl. He does that in online chats, webcams and mostly: dating apps. He loves going on a dates and playing his game, as long as possible. A few times he even managed to get intimate with people without revealing the truth between his legs. When the moment feels right, he reveals the truth, having a lot of fun in the process. Sometimes he likes to mock and question the sexuality of his victims. But at the end of the day, he wishes to find someone who will accept the weirdo he is. Maybe even someone who will play with him?

Likes

crossdressing, "trapping" men, masturbation, sex toys, cute and sexy things, power play, intimacy, cats, anime, video games

Dislikes

rejection, judgement, being disregarded, arrogance, dogs (he really is a cat person), loneliness