A Sweet Halloween That He’ll Never Forget

It’s Halloween and Jeff is sitting alone in his house. He’s feeling a little bummed out because he’s had a pretty lame year. His girlfriend dumped him three months ago, school is boring and he still lives with his parents and his sister.

Everyone else is out for the night and he’s stuck manning the door when the young folks in costumes ring the bell. He passes out candy for an hour when he wonders why he’s being such a passive loser just sitting at home on a great night to have some fun.

Halloween is the one night of the year when you can dress up like anything you want. You can act out your fantasies and your darkest desires and no one is going to know because it’s all being done under the auspices of costume fun. Jeff didn’t have any particular fantasy in mind when he started searching the house for a costume and ignoring the insistent ringing of the doorbell but eventually, he would come upon something that would change his life forever.

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One year his sister – who’s two years older than Jeff – went to a Halloween party as a nurse. Of course, it was the slutty nurse version of the costume but that’s pretty much how all costumes for girls look. Jeff found the nurse costume when he looked through his sister’s room but was hesitant to wear it because it would be pretty weird for a guy to be prancing around in women’s clothing. After making a full pass through the house and finding nothing at all he decided it would have to be the cross-dressing outfit or nothing at all.

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As he held it up and looked at the green fabric and the matching black stockings that went with the dress he figured that a guy dressed as a girl on Halloween wouldn’t be all that weird. It probably happened all the time since there were lots of guys who liked putting on women’s clothing but were afraid to do it at any other time of the year. He wouldn’t stand out at all, or so he thought.

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He began his crossdressing experiment by stripping everything but his little underwear. Considering how tight his underwear always was it’s a wonder Jeff hadn’t considered wearing women’s clothing before. He was practically wearing panties under his jeans already so it wasn’t much of a stretch to get all dolled up as a slutty nurse.

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The dress was a lovely light green colour with buttons up the front, a pocket on both sides and a dark green collar. It came with a mask to complete the medical look and a pair of sexy black stockings to complete the slut look.

He slipped the dress over his head instead of unbuttoning it and as the soft material fell down his body and caressed his skin he was surprised at the reaction he felt. Something was growing in his tight underwear.

That something was his dick and it was getting bigger because he liked the way he felt. He liked how good the dress felt on his body and how naughty it made him feel. Was it possible that Jeff was the kind of guy that was meant to be wearing women’s clothing? Was he a crossdresser?

Pulling the sexy stockings up his legs was the final part of the outfit and it turned out to be the most arousing part as well. He never knew how soft nylons felt but now he understood why guys liked them so much and why so many women loved to wear them.

As he walked to the hallway closet to find a pillowcase to carry his candy loot in he couldn’t help but get even more aroused at the feeling of his newly nylon-clad thighs rubbing together. It was creating heat between his legs and his mind was swirling with thoughts he had never experienced. Was he just a cross-dressing boy that was meant to be in women’s clothing all the time? Was it so arousing because this is how his brain worked?

With all of that swirling through his brain he stepped out the front door and started walking. He didn’t want to trick or treat on his parents’ street for fear that someone might recognize him. That could be an awkward conversation and it wasn’t worth it. Ten minutes later he was on the doorstep of a stranger’s house and he was poised to knock on the door. If he did he would be exposing himself to someone else as a crossdressing boy and it’s possible that his life would change forever. The thought of that is what drove him to knock. He was ready for something new and exciting.

As the door opened he exclaimed that Halloween tradition, “Trick or treat!”

The cute blonde girl that answered looked him up and down and when her eyes finally met his she broke into a wide smile and said, “You look great and I love your costume.”

That was the extent of their interaction but it left Jeff buzzing with a sense of pride. She thought that he looked great! He actually impressed someone with his sexy nurse outfit! He was practically skipping as he moved on to the next house, the one that would change his life forever. When he knocked on the door there it was he that was impressed with the costume. The girl that answered was wearing what could only be described as a latex fetish dream come true.

She was mixing fetish with practicality, in fact. Her top was a sleeveless red latex turtleneck with holes cut around her stomach to expose the tightness of her muscles in that area. It met a pink belt around her waist and seemingly transformed into a pair of tight red latex pants that must have gone all the way down. Jeff couldn’t tell because she was also wearing a pair of thigh-high black latex boots. She was probably scaring all the youngsters that came to her door but for the young cross-dressing man in the nurse’s outfit, it was a revelation.

This girl was a fantasy that he never realized he had. She was utterly beautiful in her latex outfit and there was an air of authority around her that he responded to instantly. She was in control and she knew it. She could easily command him to do anything and he would because her beauty and strength allowed her to command lesser beings like Jeff. That’s why when she beckoned him into her house with her finger he followed without saying anything.

He walked into her bedroom and watched as she pulled a big strap-on cock out of her nightstand and pulled it up her legs and attached it to her waist. Now she was wielding a big fake cock and Jeff had a pretty good feeling about what she was planning on doing with it.


That didn’t stop him from asking a question though, “What’s that thing for?”

Without speaking she produced a bottle of chocolate sauce and began spreading it over the head of the dildo. Although Jeff was trying to pretend that he hadn’t turned into a sissy crossdressing slut the moment she beckoned him into her house it was hard not to be transfixed by the dildo and the chocolate she was spreading all over the head. In his mind he was thinking about how it would feel to be on his knees sucking that dildo, giving it a blowjob as a good cross-dressing boy should. She must have read his mind because she commanded him to get on his knees and suck it.

“You wanted something sweet, right honey? Suck on this!” she said, pointing to the tip of her newly attached plastic dick.

When the night began Jeff was a straight man with no inclination towards cross-dressing or strapon sex, or at least that’s what he thought. Perhaps those feeling were lying dormant inside him just waiting for the right opportunity to emerge. When he knocked on her door that opportunity came along and now it was going to be a part of his life. Jeff was a little scared of what it would mean to get on his knees and suck the strap-on cock but he couldn’t stop himself.

His legs felt weak as he quickly dropped to the carpet and took the base of her alarmingly large strap-on dildo in his hand. He leaned his head forward and opened his mouth, letting his tongue snake out and take a generous lick of the dildo. The chocolate was sweet in his mouth but even tastier was the rush of adrenaline he experienced from being a submissive crossdressing boy. She had turned him into a sissy boy with almost no effort. It was the simple act of being her powerful, sexy self that made him want to perform oral sex on her strapon dildo and he probably would have done the same if she was a tgirl with a real cock.

Jeff’s life was changing at that very moment and he knew it. He was turning from a man into a crossdresser and he was doing it voluntarily. You could argue that her strong sexuality had forced him into it but the truth is his dick was rock hard while he sucked on her strapon cock and she talked to him like a little sissy bitch boy.

“C’mon sissy, I know you can suck it deeper! I know you can be a better cocksucker than that little boy. You can wrap your lips around that big dick and suck it deep. You need to get it nice and wet because I’m going to bend you over and fuck that pretty sissy ass of yours next.”


The thought of this large plastic dick fucking his virgin ass genuinely frightened Jeff. He had never been fucked back there before and he didn’t know how his butt would handle it. She might tear him open if she wasn’t gentle but he had a feeling that she was an experienced woman when it came to handling sissy boys like him and that she would be calm, gentle and quite loving when she fucked his butt. He also knew that it would take an act of God to get him out of her house at this point. He was on his knees sucking her dick like a sissy slut and nothing was going to stop the inevitable ass fucking that he had come to believe he needed.

The beautiful latex-clad babe put Jeff on his knees on her bed and spread some spit over his asshole. Her plastic cock was already nice and wet from the cleaning the sissy boy had already given it and it didn’t need much help to get into his butt.

“I’ve never fucked a virgin asshole before, sissy. I’m going to love filling your butt cunt with my big cock and turning you into my little cross-dressing bitch. Do you think you’ll come back again to get fucked with my big toy you little slut?”

She was really getting into it and the more she talked dirty to him the harder Jeff’s sissy cock got. Her dick was slowly working its way into his asshole and every inch brought a mixture of pleasure and pain to the young man. On the one hand, it felt amazing to get deep dicked and on the other hand, the stretching was pretty difficult to endure. He also felt like the manly part of him was dying on the inside and being replaced by a feminine sissy boy cock lover that would probably never go away.

The cross-dressing sexy felt so good though. It felt fantastic to have a dick in his ass and to get fucked so hard and so deep like that. He knew he’d always want more and he knew that his beautiful latex babe would always be waiting with her strapon dick to give it to him good. He knew he’d be back the next day and many days after

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