Halloween Cross-Dressing Bash Ch. 05byBOSTONFICTIONWRITER©
"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?"
"So, tell me, how did it happen?"
She was making him so hot with this incestuous talk. He couldn't believe she was like this, giving her brother a hand job. Now, he couldn't help but wonder if she flashed him her tits on purpose.
"At the time, he was going through a horrible divorce and he needed some comfort and we started innocently hugging one another. He had only been married two years. Then, he kissed me and I kissed him back. That was when he put my hand on his cock. He was on the table and I was giving him a bikini wax in readiness for the Halloween Cross-Dressing Bash. I mean, his cock was right there and it was obvious by his huge erection that he needed a sexual release," she said with her eyes starting to well up, obviously missing her dead brother.
"It's okay," he said touching her shoulder and handing her his handkerchief.
"He had a beautiful cock and I had always been curious about touching him. I used to fantasy about having sex with my brother whenever I masturbated. I was so horny back then. My husband had some sexual peccadilloes and he couldn't perform in the way that normal men did, which is part of the Glory Hole story that I might tell you if you get me drunk enough. So, I just kind of reached over and gently started stroking him," she said looking at him with a sincere smile. "It was all so very innocent. There was nothing sexual about it at all. It was just a sister comforting her brother."
"It's okay, Gloria. You don't have to finish the story, if it's too painful." He hoped she would finish the story, but he felt that he had to say that for her to finish.
"No, it's okay. I want to finish telling you about my brother. I had never told anyone this, until now. I had put it out of my mind and had forgotten most of it, until now. Telling you about the relationship we shared is cleansing."
"Then, please continue. It's probably good for you to talk about it," said Bob hoping she'd go on with her story.
She was making him so hot and horny. She made him wish his sister was like her. He wished he had a sister who gave him bikini waxes and hand jobs. It would have been erotic fun to have a sister with benefits. Then, he imagined his mother giving him bikini waxes and hand jobs. He wished both his mom and sister were more sexually open to incest in the way Gloria was with her brother. He envied their loving relationship.
"It all started when he wanted to see my tits. Well, it didn't bother me to get topless in front of my brother. He had already seen my breasts when he and his wife came with my husband and me to a nude beach last year. It was no big deal. We even fooled around in the water. He'd swim up behind me and put his big arms around me and pull me down under the water. Once submerged, he was like an octopus touching me everywhere and pulling and twisting my nipples, which I actually love by the way. I teased him, too, by groping his cock and stroking him a little under the water. We were just fooling around. It was no big deal, really and there was nothing sexual about our antics at all. We were just goofing around."
"Yeah, it was like you were kids again and playing tag in the water."
"Yes, exactly, it was as if we reverted to when we were growing up together and skinny dipping in the pond behind our house. Only, he was just horny and lonely and feeling sad, even back then because it was around the time that his wife found out about his secret and discovered that he was a cross-dresser."
"Wow that must have sucked. My wife wouldn't understand if she knew I cross-dressed. She'd want a divorce, too."
"Well, only, it was worse for my baby brother. I was seven years older than him. She thought he was gay. Of course, he wasn't. She figured he'd be sleeping with men. Of course, he didn't. It was around the time of the AIDS scare and she thought he had AIDS, no doubt. Of course, he didn't have AIDS. They were divorced soon after that. The Happy Halloween Cross-Dressing Bash was the only thing that uplifted his spirits. He made a lot of good friends there, which I'm sure you will, too."
"It's understandable that you're brother would look upon you for comfort, since you were the older sister, his big sister."
"Yeah, only, once he saw my tits, once I got topless in front of him, he wanted to feel them and once he started feeling them, holding them, touching them, and caressing them, he wanted to suck them. I admit that it was flattering to have someone, even if it was my brother, who was so enamored with my breasts. He made me feel sexy. He made me feel beautiful and desirable and it felt good to have him touch me like that."
"It's understandable you'd fall victim to that. Everyone needs to feel sexy and wanted. At the time, it sounds like you were two lonely people who happened to come together sexually, and who happened to be brother and sister."
"Yeah, well, still, at first I was a little bit uncomfortable having my brother suck on my nipples, it was more than weird. Yet, once he started sucking them and once he started fingering my nipples and pulling them and twisting them, he was making me excited. I could tell that he loved my tits. He was making me horny. I remember that I was so wet that I would have done anything," she looked at him with an excited smile. "Do you know what I mean? I would have sucked his cock if he wanted me to do that for him. He was my brother after all and we had never done anything like this before, but he was so distraught and sucking my nipples did seem to calm him, while it excited me at the same time."
"You were a good sister to have put your feeling about incest aside and give your brother what he needed." He reached down to adjust his erection and she followed his hand with her eyes. "Sorry, your story is making me a sexually excited."
"I'm sorry. I'm giving you too much personal information. Suddenly, I'm embarrassed. Sometimes, I don't realize what I say can be taken so sexually. What I think is innocent is sexual to someone else. Do you want me to stop?"
"No, please, I'd like to hear what happened."
"Well, now, that I think of it, I may have given him a blowjob, too. I don't remember. It was so long ago and I was a little bit drunk. Actually, I do remember. I was on my knees shaving my brother's thighs and he was naked. Yeah, I remember now. He started fooling around, teasing me with his cock and the more he rubbed his cock on my forehead the more of an erection he started getting. I remember his cock being so big and so hard. Except for an old boyfriend in high school and the limited sexual contact with my husband, I didn't have much sexual experience back then and it was exciting to have a cock right there, even if it was my brother's cock to experiment with."
"I envy the relationship you had with your brother. I wish I had a relationship like that with my sister. Only, she was a prude." He looked at her. She was pretty and he was sexually attracted to her, especially now that they were talking about sexual things. "I'm sorry. I've interrupted you. Please continue with your story."
"I'd reach my hand up and swipe it away and he'd pull me by my wrist and put my hand on it. Then, when he squatted down a bit and started rubbing his cock on my cheeks and on my nose while feeling my tits, he was making me so horny. Had I not been drinking, I don't think I would have sucked him off him, but I just took his cock in my hand and started stroking him before I opened my mouth and started blowing him."
"Wow, that's so hot. I can't believe you blew your brother."
"It was no big deal; we were more like girlfriends than we were brother and sister. He did cum in my mouth, though and I did swallow, but it was just a blowjob. It was much like what happened between Bill Clinton and Monica Lewinski. It wasn't like we had real sex or anything.
"Yeah, that's a good point. It was just a blowjob."
"Actually, he promised me that he would tell me when he was ready to cum, but he didn't. He promised me that he wouldn't cum in my mouth," she said laughing. "Instead, when he was ready to cum, he put his hand to the back of my head and pushed forward. He exploded his cum in my mouth. He must not have cum in a long time because there was so much of it. Then, when he pulled his prick from my mouth, he exploded more cum again giving me a cum bath. I had cum everywhere, on my tits, in my hair, up my nose, even in my ear. I mean, that wasn't the first time I had given a blowjob, this wasn't the first time that I had swallowed, and it wasn't the first time that I had a cum bath, but he was my brother."
"Damn, Gloria that was a hot story."
"He even gave me a bikini wax once when I was going on vacation to Mexico and wanted to experience a nude beach there, too."
"Really? So he saw you naked?"
"Yeah, sure, my brother saw me naked lots of times. We were always together. Shit, now that I think of it, I think we fucked when he was giving me that bikini wax. I forgot about that. Wow, I can't believe I forgot about that. We did a lot of drinking back then. We had both developed a fondness for tequila and a desire for one another. I guess now that I think of it, we were hot lovers for a brief period." She looked at him with an awkward smile that showed her obvious embarrassment. "It was just the one time, but he had made me so horny touching my pussy. Then, he started rubbing my clit and that's all it took. I remember now. I fucked my brother. I guess we did have sex. Surely, you had sex with your sister at least once growing up. Right? Surely, your sister gave you a hand job or a blowjob."
"Sex with my sister? No, I never had sex with my sister."
"Oh, well, I hope you don't think less of me because I had sex, I mean, comforted my brother during his troubled times."
"No, not at all, I'm just as excited with this incestuous story as I am that you've volunteered to help me get ready for the Halloween Cross-Dressing Bash. Yeah, that is really nice of you to volunteer to help me. I can't tell you what a load of my mind having someone to help me with my hair and makeup."
"Really, it's my pleasure. Maybe, later, you can take some candid photos of my...works of art," she said looking down at her breasts and then looking up back at him.
"Really? Are you serious?"
"Yeah, sure, why not?"
"Okay, yeah, sure, and maybe later, after a glass of wine or two you'll feel comfortable enough with me to share your story about the trick your husband played on your regarding the name of your shop."
"You'll have to get me drunk to tell you that story, Bob, because if you think what I told you about my brother is hot, you'll be out of your mind with passion for me when if I tell you the story of how my ex-husband tricked me, but we'll see."
In the next chapter Glory helps Bob get dressed and then tells him about the Glory Hole story.
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To be continued...