The Homewrecking Babysitter [MF] Part 2

Over the weekend I decided it would probably be best to stay late at the office and avoid working from home as I usually do once or twice a week but by Thursday my wife had noticed the change in my routine and asked if I’d be at home Friday. “Yeah that was my plan.” I lied.

“Perfect, me too, maybe we’ll let Avery go early and take the boys out for dinner?”

“Sounds great!” I answered maybe a little too enthusiastically, relieved that I wouldn’t have to face any alone time with Avery and possibly explain what I had done despite the fact she hadn’t seemed bothered by it.

When Friday came I was in my home office with a coffee before she even showed up. I opened my browser to a few stocks I was keeping an eye on and dragged them onto my wall monitor while on my desktop I scrolled through reddit. My wife typically left me alone when I worked from home. Whatever the time of day I think she pretty much assumed whenever my office door was closed that I was masturbating considering she had caught me twice in the past. Our sex life at this point was fairly non-existent, maybe once or twice a month so she never made a big deal of my private time seeming to appreciate that I could *handle* things myself.

The time my neighbor watched [M]e masturbate

I am fortunate that I get to work from home. After a long summer with the kids at home all day, I really felt the urgent need to let my freak flag fly for a while. For a long time I have been a closet exhibitionist, nothing too risky or dangerous. I would walk around nude in front of windows or sit on my back deck, change clothes in front of a window. Nothing like when I was younger, but no chance of getting arrested either.

My neighbor isn’t really my type. It isn’t that she isn’t attractive, just not the type of woman I am normally attracted to. She is probably late-30’s, fairly tall, relatively flat-chested, and appears to be Indian or Pakistani, definitely somewhere in that general area of the world. I, on the other hand, am mid-40’s, dad bod, average penis size and maybe slightly thicker than average. Nothing special to look at, but not repulsive either IMHO.

Now that the kids have returned to school, I decided to let it all hang out by the pool. I have seen my neighbor sunbathing topless a few times over the summer and knew that the back of her house would give her a decent view of part of my pool through a few trees. When she went out to do some gardening, I knew I had a chance for some fun.

Dirty Lax MILF [MF]

During the spring for the last few years I have coached youth lacrosse in a wealthy town near where I live. I have enjoyed this a lot and the town pays us well. I decided I wanted to continue coaching during the off-season and make a little extra money. I decided to reach out to the parents of my former players to see if they would be interested in doing one on one coaching sessions or group sessions during the off-season. One of the parents of my favorite former players’ mother, Bridget, decided this was a good idea to keep her son competitive for the years to come.

Bridget was actually the step mother of a player. The biological mother was out of the picture. Bridget is in her very early 30’s and was a slim blonde with a round bottom and small breasts. Before this I usually just saw her in leggings and workout gear. She always looked stunning.

One day I had a one on one session with her son who is a great athlete. We had just finished and the dad decided to take him over to an event that was going on in town during the summer.

[M]y dick found a home inside my [F]riend’s Ass

My friend, named Tina, and I went out drinking one night. Tina and I went to college together where we grew close. Tina is an average looking white woman with brown hair and brown eyes. She’s a little chubby and as a result she has a big butt. Not necessarily a “hot,” butt, but a big, round butt that I loved glancing at sometimes I walked behind her, fantasizing about what it looked without Tina’s panties covering it up. Well, this night I would get my chance to find out.

We drank heavily this night. So heavily that we ended up calling it a night earlier than we normally do, and in our drunken state we walked back to my house a few blocks away because we wanted to smoke marijuana before we went to bed in our respective houses. After we smoked, Tina and I looked at one another and started getting closer as we sat on my couch. Then, we just both started making out. It was just completely random, but I think that we both needed some “action,” and in the moment it just felt right. After a few minutes I took her hand and led her to me room. She followed me and once I closed the door.

[M]Y COLLEGE CUMP DUMP

The last year when I started college (male, 18):
I remember how the story started… The first day of college, we had a presentation of the year. That day I was really nervous and a little bit hyped, since I had to move to that new city. The presentation was at 10:00 pm and I was late, so I started panicking (I didn’t want to be the last and everyone stare at me) so I had to run to the room. I ended reaching there around 10:10 pm. I open the door and I see the room FULL of people, all new stundents were there sitting and listening, lots of people turned around at me (fml), there were no visible seats, so I tried to move to the back. At the middle I saw a free seat next to a girl. She saw me and noticed that I was searching a place to sit. When I reached there and I was about to ask her if I could sit but she was faster than me and offered me to sit there. Since I was so nervous and embarassed I didn’t pay attention at her, and I thought that it was just a nice act of her. Anyways, during the long and boring presentation, I could notice how she looked at me some times (dissimulating). At the end we talked for some minutes and I noticed that she was attracted to me. I wasn’t though. She wasn’t ugly but not very beatiful, just an average maybe 6/10. I though that she could be a nice friend.

[M]y girl[f]riend wanted to go to a strip club.

I think we can all agree that unexpected moments can go from “well that was shit” to “fuck that was awesome” in an instant. This story involves Angel (F.24) my awesome girlfriend and I (M.27) going to a strip club.

It was Friday night and Angel out of the blue said “Hey you wanna go to a strip club?” She didn’t have to ask me twice and I said “Sure” We took a shower together and started to get dressed when she pushed me onto the bed. She began fooling around with the button and zipper to my pants.

“What are you doing?” By the time I asked she had already taken my cock into her mouth. She was already licking and sucking and teasing my balls. “I want you to cum before we go.” She kept going and I’ll be honest I didn’t last long. Was she that good? Yes. Yes she was.

Me and My Mom’s Best friend. [MF]

When I was 18 my mom and her best friend started living together. My mom had recently gotten divorced from my dad, and her friend was single, so they moved in together. And I lived with my mom.

Now me and the friend “Hillary”, we had always gotten on well, and I started having a major crush on her because she was a very attractive woman, she was 40 at the time.

And I would flirt with her all the time, and she would always laughed it off and stuff. And sometimes she would flirt back, that was just her attitude.

And one day on the weekend my mom is a Nurse so she often worked, and thankfully she was at work that day.

And I was flirting with Hillary, I wanted to take a shower and I made sure she saw me naked as I walked into the bathroom, and I left the door open when I got in.

[MFF] [F] My funny wife got what she deserved.

One of our friends invited me and my wife Marie to their house party. We hardly ever get invited because my wife refuse to “play” at house parties. She’s adamant that she don’t want to have sex in front of or around a houseful of people.

When we walked into the house we immediately saw my wife’s friends Stacy, on all four, having sex with some guy we never seen before. He was tall and very muscular. Those are the type of guys Marie is usually attracted to. Except this guy look like he ate steroids for breakfast, lunch and dinner. Stacy was very loud as a big guy was fucking her from behind. They were in the middle of the living room and definitely the center of attention. The guy was banging the shit out of Stacy as she screamed her head off. We watched for a few minutes as the guy had his way with her.

[M]y [F]irst time at work on her last day

After reading a number of stories I felt inspired to share another one of my own! I have taken a few creative liberties because it happened a while ago but this story is 100% true. Hope you guys enjoy this one.

So this happened around 7 years ago when I was a fresh face to the advertising industry. A bit of background of myself I am 6’1 (185cm) asian with an average build and the person in my story is a 5’5 (160cm) dyed blonde amazingly fit (she was really into Yoga) body around C Cups perfect ass. It was her last day of work before she moved to London and a whole group of us had said we would all go out for drinks to farewell her but that got cut short when one of our colleagues decided to bring a 2 litre bottle of vodka back to the office which obviously escalated really quickly. I had a long crappy day and was pretty much stuck at my desk so I didn’t really join in the fun until much later but everyone was pretty much tipsy by the time I got around to having my first drink which I desperately needed by that point after a long day.

Spanking a [F] college swimmer by [m]e

During my freshman year of college I visited a friend from high school who swam for her college which was located near where I went to school. That night, I went with my friend to a party at the swim team house, which was a three story building nicknamed “the castle,” by the swim team and both members of the women’s and men’s swim teams lived there. The party was slow at first, then it got more fun as more people arrived. My friend introduced me to her teammates, including a senior on the team named Laura. Laura was a white woman with brown hair, about 5’5 or so with average sized boobs and had what I’ll call a “swimmers booty,” that I noticed when she turned around for a minute. She was wearing tight jeans and her ass looked so nice. A long story short we hit it off right away and start flirting with each other, eventually sneaking away to a secluded part of the swim house to make out. After making out for a little while Laura invited me back to her room, not too far away.