While I wrote this to work as a stand-alone story, this is essentially a sequel to "A Cruel Trick," and I'd recommend reading that story first. A lot of the content in here was originally in "A Cruel Trick," but cut out because I wanted to keep that story more about Kevin and Amy's relationship -- and I knew I wanted to give Jackie his own story. I found out that removing the missing interactions did lead to some reader jumping to conclusions about Amy that I didn't intend -- never thought the Ziploc bag would cause a conspiracy. After reading this, if some people still want to argue, "No, Amy really fucked Jackie," so be it. The delay in publishing this is the original ending was too much -- crossing over too much into horror -- and the second wasn't enough. Hopefully this third one works.
I'd also like to give a huge thanks to rnebular for once again taking the time to edit and give suggestions to improve this story. I know firsthand that editing takes time and effort. Readers really should appreciate those who volunteer their own personal time just so you can read more polished stories for free. As always, I appreciate the comments -- even the ones I disagree with. And trolls, please at least skim the story before insulting it -- some of the comments on "My Wife's Brother" were embarrassing -- for you.
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Right from just before middle-years, Jackie Robson had the reputation of being girlie. He blamed it on being raised by a single mother, with no real male role-models, and the fact she gave him a girl's name. Jackie's mother claimed his name stemmed from his father's love of baseball, who confessed it was a joke in one of the few visits Jackie had with him. Of course, this led to bullying -- though unlike most bullied kids, Jackie found out by grade six how girls tended to be more sympathetic towards him.
In high school, instead of girlie, the assumption was of Jackie being gay. He was naturally effeminate and had some personality traits of the stereotypical gay male. Initially, Jackie denied those assumptions and was insulted by the gay label. However, after experimenting a bit with a boy in an older grade, Jackie discovered without a shadow of a doubt, he was heterosexual yet different from the others. The bullying continued, but some girls actually jumped in, defended him and actually wanted to be around him as a friend. By grade eleven, Jackie was shocked that because of his female friends, who thought he was gay, he was very popular. He decided to go with it, played the part for attention because it meant hanging around with the prettiest girls in the school.
It was so easy for him to get the girls to trust him. He was shocked to find they were comfortable enough to even dress in front of him and ask his opinion on clothes. It was at a grade twelve prom that Jackie convinced the prom queen, Wendy, that he wanted to experience sex with a woman at least once. While her date was outside smoking, they had sex in a stall in the women's washroom. Over the next five years, Jackie used that approach on many women, and it worked. However, he found he got off more with the ones who were more of a challenge -- the attached or married ones. He would even jerk off thinking about some guy watching Jackie fuck his wife. Because he always used the 'trying pussy for the first time' angle, he never had to drop his gay shtick and the woman kept quiet because they also wanted the cheating to remain a secret.
He was working for the Pinehill Publishing Company for three months in archives when he met Amy Wakowsky. Her face was pretty beyond belief and her attire didn't hide much of her perfect body. The best part was that she was just moved to archives and was absolutely miserable there. There was no doubt that misery and stress would extend to her home life. Jackie was completely smitten and knew he just had to have her. Jackie always told himself that if he scored the right girl, he'd play like sex with her was so good he was no longer gay. After Jackie talked her into joining him for a coffee break during her second day on the job, he was sure Amy was that girl. All he had to do was make sure her marriage started falling apart.
With a conquest like Amy, Jackie knew he had to play the long game. He decided to focus on no other woman but Amy, and just rely on prostitutes to relieve his sexual tension. Striking himself with the bottom of a thermos, Jackie came to work with a black eye about a week after she started in archives. As Amy was consoling him, Jackie explained it was a hate crime and almost all straight men hated gays. He told Amy it probably would be best to not let her husband know she worked with a gay man and refer to him only as her co-worker Jackie. Amy admitted that she already did feel uneasy about discussing anything work-related with her husband.
After Amy consoled Jackie, of course, he had to return the favor. This started a string of coffee dates where Amy would bitch about work, and then eventually about her marriage. Jackie was who initiated the discussions about her marriage, suggesting it was her home life that made her work so unbearable -- even though he knew full well it was vice-versa. In all the complaints that he drew from her, Jackie would take Amy's side and point out ways her husband was being horrible to her that she didn't even realize. All the while, the two became closer friends, as Jackie became more smitten with her. After a month, Jackie was spending at least three nights a week doing something with Amy on top of spending every lunch and coffee break with her.
After two months, she hugged him tightly after venting about her husband who cared more about sex than her needs, and said Jackie was her best friend. That weekend, Kevin, Amy's husband, went out to watch some sporting event. Jackie convinced Amy instead of going to a movie or a lounge, to go dancing. He took a risk, offering to help find her an outfit. It paid off when he watched her model several outfits, changing in front of him just in her tiny panties. Her medium-sized breasts were just perfect, firm and perky with big suckable nipples; it was hard hiding his erection to conceal just how much he enjoyed the show.
That night was the first time Jackie got Amy really drunk and would be far from the last. He also had to stomach watching all the vultures trying to get a dance with Amy and then hit on her repeatedly. Despite being staggering drunk, Amy turned down any physical contact with all of them, though one did squeeze her ass before she slapped him.
"See," Jackie told her as he drove her home, "Every straight man finds you absolutely desirable. Kevin is a fool for not seeing that and trying to sweep you off your feet. Maybe it's time to look elsewhere?"
"I don't know..." Amy said, "I love my husband and will never cheat on him. We're just going through a thing now. He's a really great guy, really."
"But does he love you? Are you sure he isn't cheating? He was all concerned about having sex with you then stopped. Ever think the reason is he's getting it elsewhere? I just want what's best for you," Jackie said as he patted her thigh barely covered in her tight dress. He thought to himself, 'the seed is planted. Just have to pick my spot.'
Going out drinking became a Saturday tradition after that, which went on for months. Eventually, it became a Friday and Saturday night tradition along with the occasional Thursday. Jackie was starting to suspect that Amy was developing a drinking problem, but figured that worked in his favor. He had a better chance talking his way into her panties if she was drunk. However, so did other men, so Jackie was careful not to take her to anywhere that some pussy hound could steal her before he had his chance. As time went on, Jackie was getting touchier and more intimate with her while she was drunk. This turned into holding hands and pats on the legs and shoulders even when she wasn't intoxicated. Drunk or sober, Amy seemed to be getting more frustrated with Kevin -- especially with Jackie turning every small thing into a sign of marital crisis. Still, she'd tell Jackie that she and Kevin were all right, and just going through a phase. It got to the point that Kevin didn't even want sex the last time Amy decided to go through with it to try and reconnect.
"Maybe you're right. He doesn't want me anymore," Amy cried on Jackie's shoulder after having several glasses of wine, "Thank God, I have you or I'd be a basket case."
The following Monday, Amy pulled Jackie into a storage closet to talk in private. "He knows..."
"Who knows what?" Jackie asked inquisitively.
"Kevin knows about us, that you're not a woman," Amy said, "His friends' wife, June, is a server at Delta Perk. I thought I recognized her the first time we were there. I'm so stupid."
"Why? Have we been doing anything wrong? Does he know I'm gay?" Jackie asked.
"No, but..."
"No buts, honey," Jackie said, "Don't tell him. Let him stew in the fact if he doesn't take care of your needs, someone else will. Besides, everything you've told him we've been doing was the truth. Even if I was straight, you've done absolutely nothing inappropriate." Jackie knew that wasn't true, but hoped Amy believed it.
"Yeah, but Jackie," Amy said looking worried, "Kevin was already starting to get mad about us spending too much time together when he thought you were female. He's getting jealous."
"Let him. That's how he feels and has nothing to do with you. If he can't trust you enough to spend time with a friend, well, that's on him. You can't live your life missing out on fun just to spare his insecurities. Especially, when he's making no effort to appreciate the sexy woman that he has. Maybe this will be a wake-up call to get his act together? Think about this, maybe this will get you out of this bad spell and your marriage back on track. That's really what you both want, right?"
"You're right. I am so happy to have you in my life." Amy hugged him tightly and he enjoyed how great she smelled.
A couple days later, Jackie took a huge risk buying two tickets at almost five hundred dollars a piece to a big gala fund-raiser that would attract all the big wigs from town, as well as a couple B-list celebrities. It pretty much was the social event of the year. Jackie made it like a friend of his got him the ticket. Of course, he told Amy that he was going to take a male date, but that didn't go well so Jackie wanted his 'BFF' to accompany him instead. Amy was hopping as she squealed from excitement at the opportunity to attend such a high society event. Again, she gave Jackie a huge hug and a kiss on the cheek.
When Jackie joined her in the cab, that stopped at his apartment on the way to the venue hosting the gala, Amy was noticeably angry -- he knew she and Kevin had a major blowout, which was exactly what he hoped would happen. He also noticed she looked unbelievably hot in a tight black dress with a slit up her one thigh and plunging neckline. Jackie hoped that was the night all his work paid off -- buying those tickets put quite a dent in his hooker budget.
Drinks were free, and Amy wasn't shy about taking advantage. Jackie had a few, but wanted a clear head to make his move. By the time dinner was over, and the formal dancing began, Amy was slurring her words drunk. Unfortunately, all her words were about Kevin, her marriage, and how much she wanted to get back to how things were before she was cast away into archives, when her and Kevin were so happy.
