Cum Along With Me (Exclusive Feb 2025)

(All characters are consenting adults)

Winston was going through some stuff in the basement when he found an old box labeled Paul’s stuff. Winston pulled it out and was quite confused about where it came from. He didn’t know anyone named Paul, and he was sure his parents didn’t either.

He did know Paula, that was his stepmother. Did someone forget a letter? Winston had no idea but he opened it anyway curious about what was inside. When he opened it he became even more confused.

It was a ton of guy's stuff, from knives to adult magazines, some condoms and t-shirts, and even some photos of some guy presumably named Paul. Winston was starting to think his stepmother had some sort of brother that she lost.

So this stuff was probably important, so he wasn’t going to get rid of it, nor bring it up for fear of reopening old wounds. Winston began to close it when he noticed an old VHS tape inside. He picked it up and instantly knew it was an adult film.

The cover had a picture of a very busty woman nude with her fingers deep inside her, and it was called Cum Along With Me. Winston smiled, it seemed pretty good. He slipped it into his jacket and packed the box back away.

He then casually went up to his room and waited for his parents to leave so he could watch it. They had a special anniversary dinner tonight but for something other than their marriage. Winston didn’t know what it was, but it didn’t matter because it meant they were leaving.

Once they were gone Winston popped the VHS into his old television he used to play retro games on and played the tape from the beginning. It started with the logos of the companies that made it and then a strange swirl appeared on the screen.

Winston looked into it and found himself unable to look away. It then began to tell him it was going to take him on a wonderful journey into pleasure and womanhood. It then asked Winston if that was what he wanted. His mind was starting to go blank so he just nodded.

The video told him that was good, then it told him to take his clothes off. Winston stood up, dropped his pants and underwear to the floor, and kicked them to the side. He then removed his shirt and tossed it on top of them. Finally, he took off his socks and sat back down.

The tape then changed from the swirl to the woman from the cover. She started by calling Winston a good girl for watching the swirl and taking his clothes off. She then said as a reward, she would show him how to cum as a woman, all he had to do was copy her.

She sat down on a bed just like Winston was doing and she spread her legs to show off her vagina. Winston spread his legs and let his dick and balls fall down. The woman said before they could cum together, she had to get Winston looking proper.

She took her hands and placed them on her breasts, she then began to massage them. Winston of course did the same. She told Winston that massaging the breasts was a great way to make them larger, and the faster he does it the bigger they’ll be.

Winston had always loved massive breasts, so his subconscious figured he’d want to have massive breasts, so he began to massage them three times faster than the women. In thirty seconds he went from a flat empty chest to one with massive p-cup breasts and inch-long nipples.

The woman in the video praised Winston again for following instructions and told her that her new breasts were very sexy, but that was only the first step in their journey together. Next, they were going to run their fingers through their hair to help it grow longer.

Winston followed the woman and ran his fingers through his short hair, and each time he did it grew an inch longer. He did that until his hair was long enough to touch his butt. The woman again praised him for now having such long soft hair.

She then said they’d move onto his face. For that, all he had to do was close his eyes and pucker his lips like he was being kissed over and over. She then did it, and Winston followed. The first time he did it, his eyebrows got thinner and his eyes got wider.

The second time he did it, his face changed to a more feminine shape and his nose got smaller. The third and final time he did it, he was left with an entirely feminine face and a super high-pitched and soft voice. Again the woman praised Winston, saying she was looking and sounding very cute.

She then pretended to be able to see Winston and asked what else they should change while they were at it. She then put her finger on her chin and then seemingly had the perfect idea. She got off the bed, turned around, and pointed her ass towards the camera.

She then leaned on the bed and started to shake her ass up and down. She told Winston that this was the perfect way to get that massive booty and thick thighs she needed. Winston without hesitation stood up and copied the woman.

The woman then told her to do it as many times as she’d like, and that she'd wait a minute before proceeding. Winston’s brain still had no idea this was happening to him, and it simply thought that the more he shook his ass the sexier the woman who would appear would be.

Each shake caused his butt to grow out more and more, become massive jiggly balls, and his thighs grew thicker and thicker until they were pressing against each other and crushing his cock and balls. A minute passed and the woman again praised him and told him he did great.

She then sat back down and started to twist her waist to the left and then right. She told Winston this was the last thing before they went on to the grand finale. She told Winston that this was simply to slim his waist and help give him a perfect hourglass figure.

Winston again followed along and repeated what she did nearly twenty times, slimmer his waist by nearly half. Once they were done, the woman said this was going perfectly and that now it was time to make a woman out of Winston.

She took her hand and put it on her crotch. She said this would be a little hard with an unwanted dick in the way, but there was an easy way to get rid of it. She told Winston all he had to do was push it in and it would switch to a wonderful vagina.

She then began to push her fingers inside her, and Winston took his fingers and pushed them into his dick. His dick slowly began to shrink until it was so small it was starting to go inside. Once it did that it started to split open, and everything inside started to change.

Winston’s finger eventually went inside her new vagina. The woman on the screen giggled and said that Winston was now a woman and that this might feel strange at first, but what they were about to do would be the most pleasurable thing she’d ever done.

The woman then pushed her fingers in deeper and began to instruct Winston on how to masturbate in her new body. Winston followed along without any problem and before she knew it, even in a trance she was moaning like crazy.

The woman praised Winston one final time and told her that she was really close. The woman then shot her head back and moaned loudly before cumming all over the bed underneath her. That meant that Winston was right behind her.

Winston’s body hit its peak and suddenly pulled her out of trance. She then started to orgasm and shoot cum out all over her bed. She was gasping and still slightly moaning as it happened. She then sat there silent and catching her breath.

Now that she was out of trance she was completely aware of what happened to her and the fact that she was a very sexy woman with massive tits and a big jiggly ass. Once the shock passed she got up, ejected the tape, and looked at the cover.

She was hoping to find some way to turn back, but there were no instructions worse than that, it was now much later in the night and her parents were home from their anniversary date. Winston gulped, she had a lot to explain, but at least she now knew who Paul was…