Gwen’s Cock-Tail Party (Ea)(TG-Empress)

A TG-Empress request for George (All charcaters are 18+)

George’s stepmother was talking about a special party she wanted to go to with a ton of people and their kids from work; however, it required that she attend with her child, but her daughter, George’s stepsister, was too busy to attend with her.

So she just complained about it a lot, especially around George. It got so annoying to the point that George gave in and asked her if she wanted him to attend with her. She pretended like it wasn’t what she wanted, saying things like George wouldn’t enjoy it and that it was an overnight affair.

However, George knew she wanted him to agree to it. So he said he’d go. She was happy to hear it and said she’d prepare his outfit for him, and all he needed to do was come to her room the night of, and she’d get him dressed.

At the time George thought that meant she’d get him a suit; however, when the time came, what she put him in was far from a suit. When he entered her room, she started messing with his hair, brushing it all out and glueing in super long hair extensions.

She then split George’s new hair into two sections and braided each section all the way down. As soon as she finished, George got up and looked at it, then asked her what the heck she did to his hair. He then tried to remove them, but the glue held strong.

His stepmother rolled her eyes and said it was obvious. Everyone at work knew about her daughter, who she brags about all the time, so if she showed up with a son instead, they’d think she was nothing but a liar.

George protested, asking why she didn’t just tell them she had a stepson as well, to which his stepmother rolled her eyes again and said that all the other people at her work had sons and it wasn’t special; she wanted to be the focus of the party with her beautiful daughter.

Since George offered to go with her, that meant he offered to be her daughter for the night. George asked her in what world that offering to go with her meant crossdressing. His stepmother sighed and asked what the problem was. He’d look cute and have a ton of fun.

George laughed and said the problem was that he was a guy, and he didn’t want to cross-dress. His stepmother pouted and then mumbled something about already gluing the hair on George’s head. She then closed her eyes for a moment to think.

When she opened them, she asked George to make a deal with her. If he let her finish dressing him up, and he attended the party as her daughter, she’d buy him that expensive full dive reality headset he’s been asking for.

George puffed out his cheeks, and he actually started thinking about it. He really wanted that, but was it worth dressing up as a girl? His stepmother noticed he was almost convinced, so she offered him a bonus deal.

If he went and didn’t have fun, she’d also throw in a game to go along with the headset. George’s eyes lit up, and it was clear this deal was too good to pass on. George sighed and said he would do it, but he expected her to keep her end of the deal.

His stepmother was thrilled and got back to work feminizing him for the party. She trimmed his eyebrows and added a ton of makeup to his face. Stuck fake breast pads on his chest, put him in a waist cincher, then finally a tight orange dress with tall black heels.

Looking at himself in the mirror, George couldn’t even tell he was a guy, which was utterly humiliating, but it was only for one night, and knowing there was no way he’d have fun, it was an easy way to score a free hundred-dollar game.

George slowly walked down the stairs as he and his stepmother went to leave, and on the way out, George’s dad saw the two of them. He smiled at George’s stepmother but had a confused look when looking at George.

He didn’t say anything and wished the two of them a fun night. George then got in the car and awkwardly held his dress down as his stepmother drove them to the party. On the way, his stepmother informed him that he had to act as a girl all night, or the deal was off.

George shook his head and said whatever; he’d do it, but mostly because he didn’t want anyone to figure out he was actually a guy crossdressing. He wanted the headset, but he didn’t want to get it along with a reputation for being a weirdo crossdresser.

Once they arrive at the party, George’s stepmother drags him around, introducing him as her daughter Gwen. George awkwardly greets the people and then shyly stands next to his stepmother while she chats.

Every once in a while someone would hand George something to drink, and he’d sip at it. It was quite a strong drink, and after a few, he stopped being so awkward and started openly chatting with the others around his age.

George ends up really hitting it off with one of the guys, and he starts caressing George while telling him how pretty he is. George was loving it—the attention, the feeling of a taller, stronger guy holding him; it was unlike anything he’d experienced.

He was entranced by the guy, and before he knew it, the two of them were making out. George’s stepmother caught them, and while George was embarrassed and thinking she was going to scold them, instead she told them that they should find somewhere private to have more fun.

George was a bit confused, but the guy he was with was excited. He pulled George into one of the bedrooms used for the guests to sleep in during the event and closed the door. He then approached George and asked him what he wanted to do.

George knew what he was talking about, and it was a little nerve-racking. He had only ever done sexual stuff with his ex, who was a woman, never with a man, and never dressed as a girl. So he said he wasn’t sure.

The guy said that was okay and that they could do something simple. He then sat down on the bed and pulled his cock out through the zipper on his pants. He said George could simply give him a blowjob. George looked down at it and let out an awkward laugh.

He had no idea what was going on with him, was it the party vibe? Was it being dressed as a girl? Or was it something else? Either way, he was quite aroused and wanted to do it. So he got on his knees and crawled over to his cock and stuck it in his mouth.

It was long and went all the way to the back of his throat. Once it was all the way in, the guy grabbed George’s head and helped him move it up and down, and while they did that, the guy instructed George on how to give a proper blow job.

It was unlike anything George had ever experienced, a man's hard cock deep in his mouth occasionally slipping into his throat and causing him to choke or gag. Feeling him get larger and larger as he became more and more erect, and finally the taste of his cum as he unloaded.

It wasn’t an awful experience at all; it was just more intense than anything George had done before, and by the time George finished the blowjob, he was so exhausted he fell asleep with the guy’s cock still deep in his mouth.

The guy was going to remove George from his cock, but he was also exhausted and ended up falling backward and passing out as well, leaving the two of them in quite the awkward situation, one that a couple of pranksters would soon find.

A pair of girls came into the room and found the two of them passed out. They laughed at George and called him a few names before discussing what to do to them. In the end they decided to do something quite devious.

They took George’s long braided twin tails and looped them through the guy’s belt loops, then they tied them together on the other end. Once George’s hair was tied, they pulled out a container of super glue, which one of the girls claimed they got from some milf at the party.

One of them then mentioned seeing George with that milf and said that it was quite funny that it was being used on her daughter. They use the glue all over the ends of George’s twintails in order to make sure he couldn’t get them free.

As they were finishing up, they dropped the glue on George’s cheek, and it started to leak down his face and towards the guy’s crotch. The two panicked and took off before either George or the guy he was with woke up.

The glue completely empties itself in that area, sealing George’s mouth in place to his partner’s manhood. The next morning George wakes up and realizes what he still has in his mouth and tries to remove it but quickly finds it is stuck in place.

The guy woke up and looked at George and was confused, then after checking, he joined George in trying to get the two of them apart. They were unable to get George free, and all they really managed to do was make the guy aroused again and make George choke on his cock.

The two of them stopped moving and sat there awkwardly for a few minutes before the guy started trying to come up with ideas to get them free, all while running them by George. None of them seemed like a great plan, but as the guy was talking, George noticed something.

Some of the glue had come loose when the guy was moving around. George pointed at it and showed the guy, and he understood. He said he could probably get them loose by thrusting his cock back and forth. He then asked George if that was okay.

George nodded, as he wanted to get loose, and he had already given the guy a blowjob, so things couldn’t get any more embarrassing. The guy grabs George’s head to brace it and then begins to thrust his cock back and forth, fucking George’s throat as he goes.

The feeling was about the same as it was last night, when it wasn’t all that bad, and George, as embarrassing as it was, enjoyed it enough to get aroused himself. The throat fucking continued until the guy started to ooze cum into George’s mouth once again.

The guy stopped and checked the glue as he caught his breath. George was hoping for good news but noticed the guy was disappointed. He told George that they still had some ways to go, but he had an idea if George was willing to get kinky with this.

George nodded and waited to see what the guy had in mind; he wasn’t really expecting the guy to reach into his jacket and pull out a butt plug. He showed it to George and told him that it vibrated, and the vibrations would get George moving, which would help them break more glue.

He then handed it to George and told him to put it in. George would have let out an awkward laugh if he could, but with his mouth filled up, he just moved on to taking the butt plug to his butt and slipping it past his panties and into his ass.

Once it was in, the guy pulled out a remote and turned it on to max. George’s ass starts vibrating like normal, and his cock starts to get harder. The vibrations were constant and intense, but that made them that much more pleasurable.

With George squirming around on his own, the guy got himself aroused again and started to thrust his cock again. A few more minutes pass, and the guy once again unloads his cum into George’s mouth.

This time, since George already had two loads inside him, this one had a hard time going down, so a little bit came back up and started leaking out his nose. Once the guy recovers, he goes again and again, only really managing to make more cum flow out of George’s nose while breaking a little glue.

After filling George with six of his loads, the guy stopped and said that this also didn’t seem to be working. He said they needed more power, more than just they could generate. He then looked at George and said he could call someone to join them.

George turned bright red at the thought of someone else coming in and fucking him, but at the same time he found himself aroused at the idea of being taken like that. So he nodded and let the guy call a friend who was also at the party.

A minute passes, and another guy sneaks into the room and closes the door. He looks at George and the guy and smiles, saying they really knew how to party. He then dropped his pants and approached George from behind.

He pulled out the butt plug and replaced it with his own cock, then the two guys started to thrust George back and forth, fucking him from both ends. After about an hour, George had cum constantly flowing out of his nostrils and ass, not to mention his own soaking the panties he was wearing.

They were still nowhere close to breaking the glue, but at this point none of them were really focused on that, as they were all enjoying the pleasurable sex. At some point, George’s stepmother woke up and came looking for him.

She opened the door to the bedroom he was in a bit and saw him with the two guys. She smiled when she saw them. She then closed the door and laughed, saying while she had to buy him the headset, it seems she wasn’t going to have to buy George the extra game alongside it.