A few years ago when I was a sophomore in college I would always chat up the nerdy girl that worked at the local pizza place. She was always a little unkempt, had flour on her clothes and she constantly adjusted her glasses. Jackie had a very pretty face, wore no make up and was petite but just seemed uncomfortable in own skin. Over the course of a few months she began to recognize my voice when I placed my order over the phone and I would show up a few minutes early so we would have time to chat. One night I had had a few beers and was feeling brave so I asked her if she wanted to hang out after she got off work and she mulled it over for a bit but accepted. I gave her directions to my apartment and went home to have a few more beers and eat my dinner.
Category: gonewildstories
[MF] My best buddy’s widow. Part 3
Part two: https://redd.it/b0atsj
Addie and I had just finished having sex and like most times post-sex, we were in bed naked and Addie was on her stomach with her chin on her arms resting on my chest. A lot of our deepest most meaningful conversations have happened while on this position. I don’t know… Addie being naked while we talked somehow just lowers by defenses. If we were in this position and she asked me to sign over my 401K to her, I am not sure that I wouldn’t. But I digress.
“My daughter called me today.” She said.
“Is everything okay?” I asked.
“Everything’s fine. But get this, she asked if you and I were dating.”
I looked at her and a bit surprised that she was smiling.
“I guess she found out that you and I are spending a lot of time together.” She added.
“Wasn’t from me.” I said defensively.
“No, I know it wasn’t from you. Her friend from next door asked her, and she said she did not know.”
I waited for her to finish the story but maybe she wanted me to pry. So, I asked the question.
[M]eeting up with old [f]riends for a trip to the mountains. Old flames are not dead (cheating)
After a 20 year reunion from out masters degree, some friends suggested that we did a trip to a cabin in the mountains together. Since then we were mostly married or with partners and kids, some divorced and one deciding to go gay. Any how we all thought it would be fun to spend a weekend remembering and telling stories from our lives, doing some partying and exercise our skiing gear since it was in the Alps, early spring with lots of snow.
One of the girls, let’s call her Ann, and I had a special bond back then. Nothing romantic, but very good friends with “minor benefits” like kissing, massages etc. We also used each other for as cover or support if we got in a situation with someone else, getting unwanted attention, needing someone to call boy/girlfriend there and then, proving it with a kiss or something believably intimate. We shared beds also a couple of times, but nothing more happened. For some reason we did not talk more than 2 timed in the 20 years after school, busy with our families and kids.
My [F] affair with my co worker’s sister in law . [F] [FF]
My co worker’s sister in law is the definition of a hot piece of ass. She’s about 5’6, brown hair, Hazel eyes , nice plump ass and voluptuous tits. The moment I lay my eyes on her , I knew I wanted to fuck her. But I didn’t know if a) She was into women, b) if she would cheat on her husband.
Nothing happened on our first meeting. We exchanged pleasantries, made small talk, but that was it.
On our second meeting I complemented her outfit. She thanked me and returned the complement. Before I could say anything else, her husband came over and sat with us. ?
It was either on our fourth or fifth meeting that I was able to determine that I could seduce her. Her hubby was talking to my co worker’s wife and she and I were on the couch. I once again told her how hot she looked and she blushed. I then added that she could even make straight women want her. She gave me a sultry look and asked if she was having that effect on me. I replied ” why do you think I brought this up?” She looked a bit taken aback but seemed to like my response.
[MF] my love for BBWs was born!
This was about 6 years back but I’ll never forget. This girl and I, we will call her Kate, never even spoke and only spoke for a week but it ended on a high note!
Kate wrote me on Facebook and we decided to hang out and it started out innocently enough by us laying on the tennis courts looking at the stars. We got to talking and it got chilly so we began to cuddle. Now she was not super hot but had a great smile and amazing breast and was really thick!
Few moments later we kiss and she says “back to my room now?” And of course I agreed.
Once we get in there we both admit to each other we are with other people so from here on out anything that happens stays in the room. I agree and we get started.
I had never been with a BBW before but as soon as my hand slid down her panties I was a changed man! I had never felt a girl so wet in my life and Kate was dripping! Kate pointed me to the condoms and was providing me a excellent handjob to get me ready.
Getting her panties in the office [MF]
When I was lucky enough to be fucking a co-worker, I asked her a few times to give me her panties during the work day. She would do as I asked, as she was a good girl. The hottest time was when she was wearing a short blue dress and had removed her panties for me, as requested. We sat in a fully glass fronted meeting room and she handed me her panties and then spread her legs a little to prove that she wasn’t wearing any, all as people walked past. She was so nervous as she did it but wanted to be a good girl. I can’t remember how many times I jerked off with those panties but I will never forget that experience.
[MF] Busted in a car with a milf twice my age.
I’ve always had a thing for older women. Seeing Stiffler’s Mom on American Pie as a teenager and fantasizing about meeting my own version someday. I lost my virginity to a family friend and former babysitter that was 6 years my senior. But that’s a different story for another time. I want to tell you about Katie.
I was 19, heartbroken from getting dumped by my high-school sweetheart after she told me she was fucking the guy down the hall in the dorms. Yeah, she dumped me… My self esteem wasn’t great back then. I was too raw for dating or anything relationship like; I devised a guilt free search for meaningless sex. Long before tinder, Swinging and Adult Lifestyle websites were my best hope next to Craigslist.
One of my first replies was from the female half of a couple. She said she was looking for a young guy, experience unimportant. We started chatting and I was so over-eager, I’m sure. She was a gorgeous blonde married milf of 2. Her body was that of a real woman; curves, cute little love handles and a couple of stretch marks, battle scars from motherhood. She appeared confident and sexy in her photos and had a wonderful way with words. She was reassuring and kind as I nervously told her that I was new to the concept of casual sex. Our age difference intimidated me as much as it excited me. She was 41, 22 years older.
[FF] Me (21f) and my gf (23f) got down and dirty in a hostel shower
A lil tipsy while writing this!! Sorry :)
Workplace Shenanigans Round 2 [FM]
Haven’t posted in a while, but thought I would post a follow up to my first post about my workplace shenanigans.
If you would like to get a little background and the first part you can look at some of my older posts! Sorry, not sure how to link to other stories!
As I mentioned, D and I had developed quite a Dom/sub relationship, and after an intense Thursday night of sexting, I was fairly certain I was in for a fun Friday. I picked out one of my favorite, pink, lacy panties, slipped on a dress and was on my way. As soon as I got to work, D told me to come up to his office. I walked in and shut the door and before I even got the chance to fully turn around, he ordered me to take my panties off and give them to him. I wasn’t to get them back until I had edged myself in my office seven times.
[TM]Worst sex ever = Best sex ever [Mtf] discovering I am an exhibitionism slut
There was a guy I had met through a friend of a friend. He started texting and me. It was pretty normal at first and gradually becoming more sexual after a few days. At first I continued the conversation ignoring the comments but that did not discourage him. After a week of dirty messages from him I was really getting horny. To convince me to come over he told me he wanted to fuck me over the hood of his car in the driveway and he was going to fuck me like I’ve never been fucked before. As hot as it sounded I was still hesitant. Then he sent me a pic of the huge bulge in his boxers and it distroyed any resolve I had left.
Now this guy lives on the other side of town… 45 minutes away….and I know the area where he lives is very populated and there street lights all throughout his part of town.
Dressed in a short skirt that barely covers my ass, thigh high stockings, a black shear tank top with this cute little zebra stripe Victoria’s Secret bra and these cute 4in heel knee high boots and of course no panties I drive 45 minutes to his house.