See the prologue to this here – https://www.reddit.com/r/gonewildstories/comments/6z8d7g/a_new_player_has_entered_the_game_mf/
As I left Kerry’s flat that day, I did think I had maybe pushed it too far – kissing the 2 of them in front of each other and telling them I wanted a threesome could have easily ended with me getting a slap…but it didn’t. There were a few hours of nothing, then I got added to a group chat (where, I assume, most 3somes get arranged these days) between myself, Kerry and Kat. We quickly set a date…or dates – Kerry’s flat in a couple of Fridays time with the intention of being there for a good portion of the weekend.
The group chat was a good way to arrange things. Both girls were enthusiastic about it, and it was a good way to set boundaries or discuss any concerns etc. The upshot was there weren’t really any boundaries, none of us are into anything ‘extreme’ so that wasn’t a worry and we agreed that anyone who got uncomfortable could just say and step out of the situation. Also, if I don’t mention it below then just assume condoms were used, and changed, between positions/holes/girls.
I also used the group chat to play the girls off against one another – repeatedly pointing out to Kerry about how hard Kat could take it in her ass, and mentioned to Kat about Kerry’s impressive lack of a gag reflex. I also had separate FaceTime sex sessions with both girls where I was directing them exactly what to do – getting Kat to show me how she would use toys on her ass, and getting Kerry to show me how she was training her ass to relax.
There was also another moment at work – Kat and I ended up in a meeting together about 3 days before ‘3 Day’ (as we’d christened it). At the end she asked if she could chat to me about something else as others left the room, she stood up and leant back against the door and then told me how horny she’d been sitting opposite me knowing what we had planned for the weekend. She pulled her skirt up to her waist and told me to see how horny she was. As tempting as it was, this was a perfect moment for a powerplay – I slowly walked up to her, got very close to her ear and said “No” as I pulled her skirt back down. I got a message calling me a cunt (in a nice British way) as I got back to my desk.
Author: PM_UR_ASS_IN_LEATHER
A New Player has Entered the Game – [MF]
This is a prologue to the main story. I’m sure anyone who reads this can figure out where it ends up going.
I’ve written about one of the women in this story before – Kat. You can read about her and our past escapades [here](https://www.reddit.com/r/gonewildstories/comments/56arer/anal_manoeuvres_in_the_dark_how_i_m_fucked_my/)
Times passes, and Kat finds herself completely single. She’s still hot as fuck. She still wears the boots we fucked in to work. We’ve spent a couple of nights together since her divorce proceedings started, but she’s not keen on anything ‘solid’ until that’s out of the way.
The new player in this is Kerry. Kerry started working for our company as a fresh faced 21 year old out of university about 10 years ago. Friendly, outgoing, absolute killer curves. Her low cut tops kept the guys in the office happy. She didn’t stay in the company long, but she still stayed in the social group and kept a strong friendship with Kat. Kat, her and me all have similar tastes in music so we’ll regularly go to gigs together, and that’s where this all started.
Tindering around the Christmas Tree – [MF]
At the end of my last post I said I’d fuck Kat in the ass at the Christmas Party. The Christmas Party was last week and, whilst she was up for finding a quiet corner in the hotel, I said no as I knew she was (once again) back with her husband, and I have something else going on.
I’ve been using Tinder on and off for a couple of years and I’ve managed to gather a few friends with benefits/fuckbuddies – some are reliable, some have been lost along the way…others have had their numbers blocked for turning mental. I’m always up front with the women I match with – I don’t have any interest in trying to persuade someone on Tinder to sleep with me.
A few weeks ago, I matched with a woman called Anne. She is 13 years older than me, but her pictures were all enough to get me interested. A ‘fuller figure’ older woman – nothing I’d call fat, just well rounded and curvy. We chatted, and I told her I was looking for sex. She wasn’t sure, and that was enough to keep me interested. We met up with the agreement in advance that neither of us could block the other if we didn’t sleep together right away, and she promised to explain why.
Anal Manoeuvres in the Dark vol 2 – I [M] did it again with my colleague [F]
The first story – https://www.reddit.com/r/gonewildstories/comments/56arer/anal_manoeuvres_in_the_dark_how_i_m_fucked_my/
So in the 3ish years since the events in the last post took place, a few things had happened – I left the company, then rejoined at a higher role. I had loved and lost. Kat had been promoted, but had also spent some time apart from her husband. During this time she had put the weight she initially lost back on, but then lost it again and more.
Since I wrote the last story, the thoughts of that night had been bouncing about in my head (that’ll happen when you’re single!). Kat and I had still never spoken about that night, and it got to the point where I wanted to mention it, I just wanted to know what she thought of it or if she even thought of it at all. About 3 weeks ago, the planets aligned and I got a chance.
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.
Anal Manoeuvres in the Dark – how I (M) fucked my co-worker’s (F) ass because her man wouldn’t
I’d worked with Kat for a few years. We became friends through work and that had extended to being friends outside of work. Whilst I’ll happily admit she was a stunning woman, there was nothing in it from a romance point of view for me – she had been married for a few years before I knew her so I knew she was out of reach.
Kat was a bigger woman, but not fat by any means. Statuesque is the word I’d use – tall, well rounded, curvy. In her heels, she’d be around my height (6ft). When I first met her, she had been bigger but a couple of years of gym dedication and she had slimmed down. I enjoyed looking at her.
Our chats could be flirty at times, but there had never been anything remotely sexual between us and this story remains the only time anything like that has happened.
We were both sent to a conference with work – a 2 day conference with an awards dinner on the last night. We were booked to fly down the morning of the first day, and then back up the morning after the awards dinner. Our work, in their own wonderful way, had managed to cock up the hotel booking and we were booked into a hotel about 3 miles away from the conference venue, rather than the hotel attached to it.