Any time my husband and I take a road trip, the conversation always turns to sex. Once the kids fall asleep in the backseat, we talk about our sexual desires, likes, experiments we’d like to try, or will read stories to each other from Reddit. On our most recent trip, after doing all of the above, I came up with the idea of having a “sex jar”. In this jar, we would write down different sexual acts or turn-ons and periodically draw from the jar. Whatever the jar says, goes. Well, it’s been over a month and I still haven’t moved the list from my phone to papers in a jar… That’s what brings us to what happened a few days ago.
Category: gonewildstories
How [M]y ex-girl[F]riend from high school eventually cheated on her husband with me nearly 10 years later
This is a true story that basically spans an entire decade. Obviously all personal details have been changed.
I went to high school in a small town. My junior year a girl moved to the town from several states away; her name was Amy. As it turns out, Amy lived only about a mile from me, but neither of us knew that at the time.
Amy and I had several classes together, but I wasn’t attracted to her at all initially. She was quite tall for a girl (5’10” or so) and, while she was skinny, she was also sort of bulky, if that makes any sense. She just didn’t appear very feminine. She had this short hair cut that I didn’t find appealing. Her face was also not classically pretty. Her body seemed about average.
She started talking to me a lot and honestly I found her annoying. It didn’t occur to me that she was hitting on me until she became way more forward about it. At this point probably half a year had passed since I first met her. When I realized she liked me, I tried to avoid her even more, because I didn’t have the same feelings towards her. This is when I realized she lived so close to me, which I was pissed about because it meant she started asking if she could come over since I was practically within walking distance.
[MF] Training to be slutty
I met /u/Throwthethrowawaway in reddit /r/dirtyr4r, and have been having crazy sex adventures ever since. Here’s the snippets where he trains me to be his personal fucktoy/slave/slut. Read our post history for other fun stuff. ;) Tell me what you think!
Training my ass:
I’ve never liked anal or made any prepared attempt before. But the last time we met, I was on the end of a mild yeast infection. He pounded me a bit with the butt plug firmly logged in my ass. I was instantly addicted to that slight euphoric feeling. It truly is god’s loophole.
New bottle of lube, my purple 20cm/7.8 inch dildo, a condom, google hangout, I texted /u/Throwthethrowawaway “I’m starting anyway, can’t wait..” in a true cam girl fashion. (Not one, at least not yet ;)
I ran the tip up and down my ass, warming the lube, closing my eyes imagining my Dom moaning when he can’t contain himself, instantly relaxed thinking I’m his little toy, and started pushing it in. He jumped in the hangout quite quickly, I guess he couldn’t wait either.
Evening with boss [mf]
I wrote a couple of days ago about how I got a new job and I made him a promise to go see him that night, so I did as I promised. My boyfriend didn’t mind, he actually encouraged it. My outfit for the evening was a black skirt, fishnets and a green sweater. Wore dark eyeliner and makeup with red lipstick.
He text me his address and I drive out there. At red lights, thinking about what will happen. I know I’m there for sex, but I wonder how it will be. Can he get me off or will I just be getting him off? Will me being loose be an issue? He hasn’t seen my holes yet, just my butt cheeks.
I pull up to his place and he lets me in his house, glass of wine ready for me, lights are dim and he’s changed into swimming shorts and tshirt. I thank him, put my stuff down and take the wine. He shows me his place, it’s not a bad place, just not really decorated. Anyway, by the time he shows me his room, I make the comment that ‘this must be where all the action takes place’. I felt like a dork saying that but he laughed. When we get outside, he takes off his shirt to get in the hot tub. He tells me to join him but I don’t have a swimsuit (well i dont own one). Eventually after some horrible pick up lines and compliments, I undress and get in tub with him.
[MF] a week of spanking and sex: Wednesday and Thursday (pics)
Let me recap what Angela looks like, just so you know: five-six, about 150 pounds, around 30 years old. Long brown hair, dark brown eyes. Soft all over. Her breasts are probably a C or D cup, but I don’t remember exactly. She has children, and when she’s naked she’s completely unselfconscious about the changes that having children made to her body. I think she’s gorgeous and sexy. Oh, and she’s a squirter, too. Every single time.
As for me? Six feet tall, about 290 when this occurred, mid-30s, brown hair, blue eyes. My hands are pretty large. That’s about all you need to know.
[Previous installment.](https://www.reddit.com/r/gonewildstories/comments/58jemg/mf_a_week_of_spanking_and_sex_tuesday_pic/)
I have almost no memory of what we did on Wednesday, except for the fact that again Angela asked me to fuck her and again I just couldn’t do it. I did use my hand to make her come, and she did suggest that I fuck her ass — and it was just as spectacular as the last time.
How I get over a breakup: hard work and anonymousish sex [FM]
Who am I? I’m 21, 5″7 and I mostly wear a size 4. My bust size is 32C and I have brown almost black short hair and brown eyes on a wide friendly face.
I hate breakups. I mean, that isn’t exactly shocking news. Like, I didn’t say I hated cuddly little puppies who lick your face when you are feeling sad. Or sex. Because that would be fucking ridiculous. But it’s still true. I hate breakups. In the aftermath of a breakup, even ones that I initiated, I feel like I’m on a scary roller coaster and want to get off but it won’t stop.
Tom and I broke up. I was the one who broke up with him but somehow it seemed like he took the news in stride while I was a quivering mess.
“Wanna fuck one last time?” he asked when I told him we were done in the coffee shop where we had met, that mischievous smile of his that I can’t resist settling the question for me.
I headed home from his place and when I got there, threw on crappy old sweats, turned Bravo on mute and listened to 1D’s Up All Night on shuffle like a million times. If you hate on 1D, I don’t want to know you.
[TM] Losing my trans virginity, age 21 *TRUE STORY* [crossdress] [convincing] [detailed]
So I’ll quickly give some background before I go into the story. At the time of encounter I was 21, living in *a city* while at uni, and was crossdressing very convincingly pretty much every free time I got. I even had a profile on a *well-known site* that was getting lots of positive comments and I was breaking into the Top 10 T-girls on that site- pretty impressive considering I have never taken hormones! So I got talking to a guy on that site about meeting up and one night I just went for it! Here’s what’s happened….
[MF] Could this be called maid service?
One more tale from the vault. This is the last really insane one. I’ve had plenty of other experiences at events, but they are usually more mundane, never getting much crazier than a clandestine quickie against a forklift in the service corridor or a rousing game of Celebrity Strip Cards Against Humanity.
This is another one of those stories that has a postscript to the action that makes it all the better IMO. Not sure why, but I seem to have a thing for knowing what happened when others don’t.
*Shrug*
Anyhow, here it is.
I was at a con one year that had a maid cafe. I somehow pulled the short straw, and had to report for setup duty at 6AM on Saturday morning (This is the WORST shift imaginable, since you can’t stay up on Friday night.) I was assigned to help set up the maid cafe. I head to where I am supposed to be, and a friend of mine (Deacon) is there. We start setting up, and he tells me that he brought his 18 year-old sister, Elly, this year, and that she was going to be participating in the cafe. I told him that was cool, and we kept on working.
These boots were make for walking…and fucking – How I [M] fucked a MILF [F] and picked up a fetish
I was 24 and fresh out of University, and started a job with a fairly large company.
My time with the ladies at uni hadn’t been prolific – I’d slept with 2 people in the 4 years. My main reason for this spell was my self-confidence…I had none! I was about 15 stone (210lbs or 95kgs for those in the new world) heavier than I am now. Girls rarely looked at me, and those who did would let my advances down with “I bet you give great hugs”. So I rarely tried anything.
I started work and there weren’t any in the office of a similar age to me. There was one woman in the office who caught my eye – Claire.
Now the first thing I’ll say is that Claire was not technically a MILF…she had no kids, however she was 12 years older than me and very attractive, so MILF will do for a description.
Not long before I started with the company, Claire’s husband had walked out on her and moved to Portugal to live with a girl he met on a boys holiday.
Got freaky with my friend’s aunt at her bachelorette party (FFMM) [Group]
A few years ago when I was 24, I got invited to a real bachelorette weekend blowout for a friend. I had a few friends get married right out of college, but they were typical of poor new grads: maybe a bar crawl or something. “Tiffany” had something completely different for her: long Memorial Day weekend extravaganza in Chicago. Tiffany was rich: Her dad invented toaster strudel or something (not really), but pretty down to earth. Her aunt apparently offered to pay for her bachelorette, so all I needed was a ticket to Chicago.
Now her aunt “Marie” was another story entirely. I was expecting someone our parents’ age, possibly outraged by vibrators and penis straws, offering me a Werthers or something. Marie was definitely the young cool aunt of this loaded family. She was early 40s, recently divorced, and readily reminded us *No prenup! Half plus alimony!* And I could tell as soon as we met that she was on the prowl: about 5’7”, dark tan and fit, wavy black hair with blue eyes, and big, presumably fake tits. Had a solid MILF vibe going on.