The time I fucked my attractive step mom [M] [F]

I know what your thinking, this kind of stuff only happens in porn right? This actually happened and it’s one of the best things that’s ever happened to me, so let’s start at the beginning.

Shortly after I graduated from Calvin College in Michigan, I went to go live with my dad for a couple of months until I found a job to be a therapist (I got a degree in Psychology after all).

So I’m on my way to my dad’s with my things and I call him to tell him I’m on my way, and this woman picks up the phone with a lovely tone of voice saying “Hello?” I say “yeah, is my dad there?” And she said “He is in the shower, and he told me to pick up the phone if you called.” I say “oh ok, may I ask who you are exactly?” And she says “not at all, I’m Charlotte your new step mom.” And with a little bit of excitement in my voice I say “well it’s nice talking to you, we’ll meet each other when I get there” and we both say bye before I hang up.

[M]y Last Night With A Married Couple [MMF]

So after my [last](https://www.reddit.com/r/gonewildstories/comments/dn7b1c/a_more_pleasant_encounter_with_a_couple_mmf/?ref=share&ref_source=link) fling with the Ds Wife and husband couple we spent a few weeks chatting before they went radio silent for a few weeks.

I figured they had just decided to move on or something and started looking for other people to hook up with when I got a message from Carol. Turns out Steve had gotten her pregnant and but she hadn’t told him yet because she wanted to make it a big night. And apparently that meant she needed me.

After having so much fun fucking her husbands face I was interested in seeing what she wanted to have me do for them this time so I agreed to meet up. Carol and I discussed the details and she told me she wanted to go farther than last time and have us take turns fucking his ass.

This had me at attention since I had could barely take my eyes off of his little bubble butt last time and so we set a date for that Friday.

[M]y mother-in-law sucks my cock on the regular. Never underestimate the blowjob skills of a sexually frustrated 50-something woman.

I’m a married dad of two kids. My marriage is basically good, except that my wife struggles with mental illness. She’s been on antidepressants for years and has really bad mood swings. She’s a great mom and while our marriage is occasionally a challenge due to those issues, we get through it. She’s a good woman who just suffers from an illness. A big drawback of those meds, however, is that my wife has had basically no sex drive for years. We are a total dead bedroom.

My MIL is great – mid-50s, quite fit, funny, energetic lady. Longer strawberry blondish hair and big, mom-of-three-grown-kids tits. She loves me (so does FIL), both because I’m a decent dude and because I think they understand the challenges that my marriage to their daughter entail. We all have a great relationship. Especially these days.

About two and a half years ago, I popped over to the in-laws house one afternoon to drop off a casserole dish. MIL is around and insists I come in. She was wearing around-the-house shorts and a tank top of some sort. She was in a really good mood, and I realized she was probably a glass or three into a bottle of wine. She let me know that her husband (FIL) was out boating and wouldn’t be back for a while.

[MF] Girlfriend told me story about her one-night stand.

My girlfriend and I have this thing we do, when she’ll give me a handjob and whisper sexy stuff in my ear. She’s always told me she’d only had sex with previous boyfriends and never done anything too wild, but last night she told me a secret. Here’s what she said, as close to word-for-word as I can remember….

“It was back when I was sharing a flat with Julie. I’d been out clubbing but she had stayed home with her boyfriend. He was visiting for the week and one of his pals was crashing on the couch for the night, can’t remember why. I got in about 3am, expecting them all to be asleep.

The pal was in the kitchen, getting a glass of water in a t-shirt and boxers. I was a little tipsy, so said hello and we chatted in the hall for a bit about the usual stuff. I’d met him before but didn’t really know him well.

We didn’t flirt much at first, but I knew he was looking at me, he couldn’t help it. I’d been clubbing so was in a little blue dress and stilettos, my legs tanned, make up that little bit sexier than it was when I last saw him. I knew I looked good and I’d kissed a hot guy earlier in the club, so I felt good too.

Our first time sharing her

Our first time was in Seattle Washington, on my 45th birthday trip. One night, a month or so before-hand, she asked if there was anything special I wanted to do in Seattle for my birthday? Offhandedly, I said “yeah, finally have a threesome with you and another guy . . .” This wasn’t the first time I had expressed a fantasy of sharing her with another guy, preferably someone she found hot. Her reaction was, of course negative. “This again?”

“Alyce, I don’t have a lot of things on my bucket list, there’s swimming with sharks, going to London and Paris and sharing you in a threesome. You asked me what I wanted to do and I told you. I get you aren’t interested, but hey, it’s what I would like . . .” She gave me a dirty look and walked away.

Three days later, after putting the kids to bed, she comes into the bedroom and tells me “I will try this once, and then you can never ask me to do it again. Okay?”

How I got to where I am, true story, male to female

I figure most would not be interested in this, but I figured I might tell you all a story of how I got to where I am now and why failed as a man and seeking to fully feminize now. I’m also just curious on if this is a turn on for real men unlike myself.

For as long as I can remember, I always knew I should of been born a girl. Many little things like being naturally passive. When role playing games I rather be the princess then the knight, Stuf like that. Anyways, I grew up in a pretty tradional family. Had a stay at home housewife/mom. My dad was clearly the head of the household. I have all brothers and they are all manly men type of guys. Cowboys, bikers, football fanatics, that type of thing. My main interest during the time was video games and still is.

The time the call girl[F] hid [M]e in her kids room so I could fuck her more

So after a few years of dead bedrooms I had enough and while the family was out of town with the in-laws I decided to try to get a hooker or whatever it would take to feel some physical companionship. So I found this woman on craigslist (back when it worked like that!) got the address and headed over to the next town, about a 25 minute drive. Paid some cash for a blow job and she pulled my pants down. She told me I have a porn dick. I was like, “What do you mean a porn dick?” And she said “The type of dick you usually only see in pornos””Aw I bet you say that to all the guys!”

She gave me a great blowjob and wanted me to fuck her no extra charge. But she had another customer or two coming after me, would I hide out in her kids room so I could fuck her some more? (the kid wasn’t home so..) Um … sure!

Snowed In [MFF]

A few years ago I was house-sitting for some family friends as they took a winter vacation somewhere warm. They have a large farm out here in the midwest, about 20 minutes from the closest city. They’re retired, so there wasn’t much to do in terms of chores, they just felt better about having a dude in the house rather than leaving it empty for several weeks. It worked out well for me; I got paid to live in a nice, quiet house away from the city. I used my time to study and relax, and apparently to luck my way into a threesome.

At university, I was looped into a group project with Emma. I’d known her pretty well from previous classes. I would call us acquantances, not quite friends. We had chatted occasionally but I honestly couldn’t tell you much about her personal life. But she had a fun personality and I knew she worked well, so I was happy with my assigned partner. She was a short, bubbly girl with brown hair, a pleasant face, and a curvy body. A little bit curvier than I usually liked, but her fun personality brought her up a few points on the attractive scale. Truthfully, she was more into me than I was into her. Her eyes lit up when she found out we were grouped together, and she touched my arm frequently as she gushed about how much fun we were going to have as partners.

[MF] getting a blowjob from my mates gf.

Ok. Bit of background here. This all happened a years ago when we were all fresh out of highschool, 18-19 year Olds. My friend Andrew was going out with his highschool sweetheart Ellie.

Ellie was thicc before thicc was a thing. (Around 2013) she had nice green eyes, jet black hair and a truely amazing rack. Despite being slightly chubby her tits were full, firm, round DDs. I’ve frankly never seem tits that match up to hers, and they were her pride. Definately her stand out feature. Which is saying something because her ass was round and firm too. On top of that she was sweet nerdy girl. Into Minecraft and things like that.

There was some history already between the three of us, me and Andrew having tag teamed her once before that. And Ellie showing off her tits and masturbating for me over Skype. All through school she had been a geeky chic, and was only now the year after starting to awaken her slutty side.

They lived with Andrew mother in this big fancy house out of the city by the boat club. And she was away for the week. So of course Andrew had me and a few others around for a games night.