His cock was sliding between your well oiled ass cheeks. You even moaned when he pressed against your tight virgin asshole. You were basically begging for it by this point. But you started to wonder how you had ended up in this situation?
Three years had passed since this story started. You two met at a job event, some sort of team building. The actual gains for the company were minimal, but it was a great succes for you personally. His name was Liam and you too had gotten along very well. Talking mostly about video games you both liked.
In the end he invited you to play the video game in question over at his place. Apparently, he had Wednesday afternoons and evenings to himself. His girlfriend had yoga class and would always have dinner with her friends after that.
The in question Wednesday was no different, Liam played games all evening long, except this time he had you as company. Then after the last game Liam did something unexpected. Without prior notice, he switch over to porn on the TV. You can’t remember exactly, but you do think it was Piper Peri getting railed by a BBC.
You were on opposite sides of the coach when it happened. Liam, without hesitation, unbuckled his pants and let his monster loose. You were both shocked at what he was doing and the size. He quickly explained that you too, were welcome to pleasure yourself and enjoy the movie. It was surreal, but for some reason you listened to him.
You both came, you first and he a bit later. Liam reached over towards you and handed you a paper towel. After cleaning up he thanked you for the company and you parted ways for that time. What you didn’t realise was what you had started.
It became part of the routine. Every Wednesday you would take the number 45 bus at 2:34 PM towards down town. At 2:47 PM Liam and you would already have started your first game. Around 7:30 Liam would switch from his PlayStation to his porn video of choice. Then you would both do your deeds and clean up.
One time his girlfriend came home early. You were shocked, but he continued. Apparently, she knew of this who relationship. She calls you Liams jerk buddy when they talked about you. It was another surreal moment and you thought it could not get weirder than this.
You were wrong. Ohh so wrong you were.
Liam’s and his girlfriend’s relationship was great, until it wasn’t. She had moved out and left most of her stuff. You never really understood why. With her out of the picture your weekly routine became a daily routine. Everyday after work you would play games and jerk off.
As the weeks passed by Liam started the porn earlier and earlier. Edged and jerk off for longer and longer. On your birthday he even got you matching flashlights in the form of Mia Malkova’s ass. It became more and more normalised until one day when it changed.
Liam asked you to go in the bathroom with him. He opened the top drawer and it was filled with his ex’s make-up. You looked at him in the mirror as he asked you to put some one, just for fun. In your younger days, your sister had been fond of putting make-up on and so you knew how to do it.
After putting on your make-up you both returned to the coach. Fucking the silicon replica of Mia’s asshole. Liam was extra excited this time. He came so hard that it made you nervous for a second.
From here things would only escalate.
The make-up became part of the routine. You’d even catch an earlier bus each day get ready earlier. He constantly complemented you and made suggestions on how you could improve your look. Longer hair, a darker lipstick and so on.
After few weeks of this Liam took the largest leap so far. During a jerk off session he suddenly stopped. Stood up and told you to follow him. Both of you made their way to his bedroom where he opened the wardrobe. His ex had left almost all of her clothes. It was quite the collection and Liam reached for a pair of bright pink yoga pants and a matching tank top. He gave them to you and told you that you should try them on. If you liked them you could keep them.
And indeed, you did like them. They fit you perfectly, even better than they did on the previous owner. You finished that session with you own cum staining the bright pink yoga pants.
The next day you got a pair of booty shorts and an orange bikini top. It really fit you well, but the bikini didn’t do much lifting if you were honest. That day would mark yet another point of no return. Liam asked you to jerk him off. It was shocking, you were strictly hetero and it didn’t at all interest you.
But something in the back of your head told you to do it. Told you that a simple hand job would not constitute as “gay”. You scutched over to his side of the coach and grabbed his massive shaft. It pulsate in your hand and you took your first stroke of another man’s cock.
And ladies and gentleman and others, how you got from stroking that cock to having it seconds from being pushed into your ass, is story for another time.
Ciao.
Source: reddit.com/r/eroticliterature/comments/wa46vh/getting_over_your_ex_part_1_m_sis_trans