Getting Lucky with My Housekeeper [MF]

So I live in a pretty wealthy family with both my parents working. Because we have a big house and both my parents are busy with work, we hired a housekeeper or maid to take care of things around the house. She comes M-F to cook, clean, do laundry, etc. We’ll call her Maria. My parents and I both, while busy with work, actually work at home. Therefore, we have grown close to her. She will come over for Thanksgiving, Christmas, etc. She’s basically a part of the family.

At the same time, I’ve been attracted to Maria for a while. She’s a bit older than me, probably being in her late 40s while I’m 28. However, she has a great body. Her best feature is her ass which I have started at for years now. She and I have grown close as well. We would message on WhatsApp and she has sent me plenty of dirty jokes that she has received from her friends. We’ve talked a bit about sex and she’s pretty open about it. However, she was married so I didn’t try too much. I may have tried flirting a bit but that’s about it. About a month ago though, I found out that she’s getting divorced. However, with the age difference and the fact that she works for us, I didn’t really think anything will come of it… until.

Midnight Kiss Leads to Much More [MF]…

It was New Years Eve and I still didn’t have any plans. What was I going to do? Was I really about to spend New Years Eve at home? I was pretty desperate. I had even posted on Facebook asking what is going on with no real responses. Finally, I get a text from my younger brother asking me if I wanted to come to a party at his girlfriends place. He told me it will probably be a small get together between 6-8 people but hey, that was better than nothing. I asked if any babes were going to be there. His response was “yeah, and one of them has seen your pics.” I had no idea what that meant! What did the girl look like? What did she think of the pics? My brother refused to tell me!

As time was getting closer, I started to get nervous. Honestly speaking, I get pretty nervous around girls. I’m not some macho guy so suave talking Don Juan. This is a small party. What if the girl was really ugly but I couldn’t really avoid her because there were so few people there? What if she was smoking hot but wasn’t actually into me? My brother has been known to fuck with me. So what do I do to calm my nerves? I masturbate.

How it started with my ex Part 3 [MF]

I woke up on Friday very nervous. It’s not every day you go over to someones house specifically for a blowjob. I smoked a small bowl to calm my nerves and I got to her house around 3. Her mom wasn’t due home until a little past 5. She greeted my at the door in a cute little outfit, gave me an awesome hug, and let me in. We get to her room, and pretty soon, we are making out. I start feeling her breasts. I take of her yoga pants but keep her panties on. They were cute. I think take off my pants. We go back to making out and grinding. I go to take her underwear off but she tells me to go first.

I take of my underwear. I tell her it is her turn but she wants to play a bit before hand. I’m not going to complain. She basically starts giving me a handjob while she was on the side making out with me. I start rubbing her pussy through her panties and I can tell she is damp. I slowly take her underwear off to enjoy the view. She has a small little pussy with shortly trimmed pubic hair. My favorite! Eventually, our shirts both come off as well. We are not both entirely naked, on top of each other, making out and rubbing each other.

How it started with my ex Part 2 [MF]

Okay, so I posted my earlier post 3 weeks ago saying I was going over in a week for a blowjob. That didn’t pan out for a while. The first Saturday, she was sick and the second Saturday, I was out of town. Before I go into the main event, let’s fill you in on what happened throughout those weeks. I’ll post Part 3 (the main event) next.

The first Saturday, she was sick. However, she wasn’t contagious and wanted to buy a bit of weed from me so I went over. She told me that we can hang out but she wanted to really enjoy the blowjob so we would have to hold off on that. She started feeling a bit better after a couple bong hits so we started making out. It started as such soft kisses but pretty soon, she was lying on top of me, grinding, and making out hard. I felt her breasts over her shirt. Then I put it inside her shirt and felt them bare. She was moaning into my mouth. Soon after, she stopped kissing me and looked like she wanted to say something. Before saying it though, she changed her mind and went back to kiss me. I stopped her and asked her what she wanted to say. “I don’t want to tease you since I can’t get you off”. I was super turned on but I had to know. I pressured her a bit. She leaned down and whispered in my ear “I want you in all my holes.” God DAMN. We had talked about a blowjob but that sentence alone made me almost blow my load. I realized she wasn’t ready to do that. In fact, after talking about it, it was clear that while she wanted it, it wasn’t going to happen unless we were together.

How it started with my ex Part 1 [MF]

Background:
So I met my ex, let’s call her Chloe, back in 2006. I was super into her and we quickly became best friends. Yes, ladies and gentlemen, I was put into the friend zone. I asked her out 3 times and each time she said “she didn’t want to ruin our friendship.” Eventually, in 2010, she decided to give me a chance. It started off great. We even got engaged but we eventually ended in 5 years later. I stayed away from her for a while to clear my head and all and then she got another boyfriend. They ended up breaking this summer.

The Start:
I’m a pretty liberal person when it comes to sex. For me, if it feels good and it doesn’t hurt then it can’t be wrong. It is like smoking weed. It’s a “victimless crime”. She, on the other hand, doesn’t think that way. She told me before any of this happened, and a few times since, that she would “never EVER have sex outside of a committed relationship.”