"Oh, it was years ago since my brother's murder. I still miss dressing him, though, helping him to get ready for the Topsy Turvy Happy Halloween Cross-Dressing Bash. That event was always the highlight of his year and that was fun for me, too. He was the sister that I never had and we were so very close," she said with a laugh. "I was thinner then and we were the same size and he was always wearing my clothes and whenever he bought a new outfit, he'd share it with me, too." She looked at him and smiled. "I can help you get dressed, if you'd like. I can even shave your legs or your back or your chest if you'd like me to or want me to do that, along with doing your hair, makeup, and painting your fingernails."
"Really? That would be so great if you could help me get dressed, help me with my makeup, loan me your wig, paint my fingernails, and shave my legs and my back in readiness for the Halloween bash."
He imagined having legs as smooth as silk. He imagined her helping him put on his pantyhose. He imagined her seeing his cock for the first time and him getting an erection with her look. He imagined himself with a huge boner sticking straight out of his pantyhose and her reaching her hand inside, taking hold of his cock and wrapping her fingers around it while trying to adjust him to make it look more presentable.
"Yeah, sure, no problem, I used to do that for my brother. I even used to give him a bikini wax," she said with her cheeks suddenly looking a bit red. "I mean, it wasn't sexual or anything like that, although I did have to hold his cock to move it out of the way while I waxed his balls, but it was no big deal."
"Really? Wow! That would be so nice of you, if you could do that for me. I don't mean holding my cock. I mean, if you could give me a bikini wax. I can hold my own cock. You don't have to hold my cock for me."
"No, really, I don't mind. I'd hold your cock for you, too," she said giving him a wink and a sexy smile.
"Okay, that would be great if you could do that, too," he said giving her a lustful look that culminated in him staring at the huge impression her tits made in her dress.
Suddenly, he had the image of Gloria holding his cock while giving him a bikini wax. He imagined her stroking his cock while he felt her big tits and fingered her big nipples. Suddenly, he had the image of Gloria holding her brother's cock while giving him a bikini wax. He imagined her stroking her brother's cock while he felt her big tits and fingered her nipples. She was driving him wild with this sudden sexual conversation.
He couldn't believe she was telling him all this without any sexual emotion. She talked about it, as if she was talking about how to make beef stew. She was making him so horny with all this incestuous, sexual talk. He was fascinated that this woman could be so candid and so erotic while seemingly acting so innocent, albeit she did get a look of embarrassment when telling him about having to hold her brother's cock.
"Okay," she said laughing, "now that I remember it, he did get an erection every time I touched him and every time I held his cock in my hand to move it out of the way. My brother had a big cock, too. He was always so horny and was always feeling my tits at every opportunity. Maybe because his wife was flat chested, but he loved my big tits. Besides, it was just horseplay and innocent teasing between brother and sister, you know. Nothing ever happened. It wasn't sexual whatsoever."
"Well, I think if my sister held my cock, I'd get an erection, too. Only, if my sister held my cock, I'd think it was sexual. If my sister held my cock, I'd want her to jerk me off or blow me. We must have had a different relationship than the one you had with your brother, I guess. Guys are all such horn balls."
Suddenly, he imagined his sister holding his cock and his sister giving him a slow hand job. Now, that he thought about it, there was that time, a few times, she walked in his room unannounced and caught him jerking off. He was always jerking off and she'd always stare at his cock before leaving the room without saying anything about it, not even apologizing for barging in on him.
He wondered if she did on purpose. He wondered if she knew he was jerking off, heard him jerking off, and took the opportunity to barge in his room to catch him masturbating and to stare at his cock. He never considered that as a possibility, until now, and until talking to her about her brother.
He always just felt embarrassed. He always just felt perverted. He thought he was the only one who jerked off numerous times a day, every day. Back then, he never realized that all guys his age masturbated.
Bob thought of his sister growing up. Although he always wanted to, he never felt her tits. She never gave him a bikini wax or held his cock for that matter. Except for the looks he stole through the keyhole when she was changing for bed, and jerking off over what he saw later when alone in his room, that was the extent of his incestuous encounter with his sister. With all this incestuous talk, he remembered he used to do that same with his mother, too.
He remembered he'd watch his mother through the keyhole getting undressed, only to jerk off over what he saw later in the privacy of his bedroom and in his bed. Then, he remembered all the times he tried on his mother's and sister's underwear, panty and bra, and jerked off while wearing it. He wondered if they knew. He wondered if they suspected. That was the first time he experimented with cross-dressing and now, he was about to take the biggest step when attending the Halloween Cross-Dressing Bash. Finally, he was going to see himself all dressed to kill as a woman.
How could he possibly forget that he used to dress up in his sister's and his mother's underwear? That was so exciting to prance around while wearing their underwear. He couldn't discern if it was so exciting to wear women's panties and bras or if it was even more exciting to wear his mother's and his sister's panties and bras. He wondered if that was incestuous behavior. Probably, it was. Now, this story that Gloria was telling him in confidence had him more than excited and he hoped she'd tell him more to make him even more excited. He never considered cheating on his wife and adultery, until he met her. Now, except for the Happy Halloween Cross-Dressing Bash, she was all that he thought about.
"Well, there was that one time that I gave my brother a hand job," she laughed and turned a bit red again.
"Seriously? You gave your brother a hand job? Wow! No kidding."
"Yeah, I mean, it wasn't intentional or planned, it just happened. We were just both caught up in the moment."
"How old were you?"
"Oh, God, I don't know he was maybe 25-years-old or 26-years-old and I was in my early thirties. That seems like so long ago and it was. Wow, I can't believe it was nearly ten years ago. Where did the years go?"
