Billie's Story (Story of the Week)

"I don't know exactly when I started wearing female underwear."

Is the opening line to author's Wild Billie tale named Billie's Story (Crystal Story Site.com). In this lovely 2003 erotic tale we  follow teenager Billie as he discovers and experiments first with his mother's and sister's clothing and more intimate items sometime during the late 1950's and possibly early 1960's.

Billie's secret obsession with women's clothing rises after he moves in with aunt. Sometime after turning 16 he befriends his beautiful neighbor named Janet and shortly after he begins doing odd jobs around her house. Unknown to Janet and her husband Jim (besides that Billie is closeted crossdresser) is that they're love making has been witnessed on occasions by Billie through the couple's bedroom window exposing Billie to Janet's beautiful body and most intimate private moments.

Billie's fascination with dresses, bras and panties leads him to enter the couple's home one Summer day and try on Janet's unmentionables. Trying her clothe's is short lives when Janet returns home early and finds her her 16 year old teenage neighbor boy wearing her lingerie and attempting to wear her little black dress.

Overcome with immediate regret and shame he sincerely apologizes and confess his secret obsession to Janet, but instead of blackmailing him and punishing him, she is understanding and tries to calm him.

Finding her teenage friend in a dress like a girl intrigues and seems to arouse Janet. The sensual, but understanding Janet then agrees to help Billie explore his latent femininity.

She wouldn't tell my aunt about my dressing habits and I would not tell about our lovemaking. She got up on an elbow and looked at me for a second then said I really did look good as a girl and that she would enjoy helping me play that role. She would dress me and make me up and since she did not have children I would be like her daughter. I thought this was strange but as she said it she started to gently rub my cock into a full hard-on and I immediately agreed. She said it was time I lost my virginity

The story is told in first person and is claimed by the author to be based on his real life experience with his female neighbor when he was a teenage boy in the late 1950's early 1960's. Either way, Billie weaves a beautiful narrative that feels more like an excerpt from a well composed biography than a short story found in the depths of an internet. That's not to say that the more intimate scenes in the story are dry and void of spice. No, its the contrary. Once the characters in the story become intimate you the reader feel every twitch and feel the sweat that comes from their bodies. The visuals that the author paints with words are a candy to the brain.

As I mounted her she led my cock into her pussy. God what a feeling as my cock slipped fully into her hole. I thought her mouth on my cock was amazing but her warm moist pussy felt even better. I started to move in and out as she guided me by grabbing my ass with both hands. I don't know how long I lasted but I know when I came that time it felt wonderful. I could feel my cum injecting into her body.

Billie's sexuality and sexual experience is furthered explores when Janet brings her husband into the mix. Slowly and patiently, Janet introduces Billie to the role of the female in bed with her man.

The story ends on a sentimental note and may sadden some of the readers, but it may have been more tragic had Billie not explored that side that's in many of us. That would have been the real tragedy.

Thank you Wild Billie for this sharing a small part of your life with us.