[MFM] (23F) My new kinkfriend (26M) is officially locked in chastity now, and I am his keyholder!

My FWB recently revealed to me that his roomate loves to listen to us fuck…then things got REALLY interesting!

About a week ago, I posted on /r/sex, as well as one update. Here they are if anyone wants to read them:
[1st Post](https://www.reddit.com/r/sex/comments/6lrgml/23f_i_got_asked_by_my_fwbs_roommate_26mif_i_would/)
[2nd Post](https://www.reddit.com/r/sex/comments/6mbo2o/update_23f_i_got_asked_by_my_fwbs_roommate_26mif/)

Short version for those 2 posts:
My well-hung-and-knows-how-to-use-it FWB has a chubby, nerdy, but as it turns out kinky roomate that has been listening, and jerking off, to us fucking. We’d slowly become friends before I found out. Once he realized I know he’s a perv and am totally cool with it, he worked up the courage to ask me if I’d be the “keyholder” for his chastity fetish. My first post was reddit helping me weigh the pros/cons. My second post, I let him know YES, I am in! And then reddit gave me more ideas/suggestions to proceed. And to figure out where I should be posting future updates… which is how I ended up HERE! ;-)

For anyone catching up or joining in fresh, this will include the sexy hung roomate I refer to as my “FWB”, and the chubby pervy micropenis roomate will continue to be referred as “Nerdvert”. I am the sexy young woman jumping head first down the rabbit hole of kinky sex and chastity fetish.

Yuppie Couple, pt. 2 [MFM]

First time with this couple:
[first time](https://www.reddit.com/r/gonewildstories/comments/6iti27/the_shy_girl_mf_and_the_yuppie_couple_mfm/?ref=share&ref_source=link)

The night leading into this post:[at the brewery](https://www.reddit.com/r/gonewildstories/comments/6nsqir/leading_up_to_round_two_with_the_yuppie_couple_mfm/?ref=share&ref_source=link)

**Quick prelude**
If you haven’t read the lead-in to this post, probably should start there for descriptions of us as well as exactly what happened at the brewery before we went back to there place. One sentence summary: I was invited by Mike and Britt to join them for another threesome, after helping to make one of their “friends” jealous.

**Back at their place**
It took a while to drive to Mike & Britt’s place in Bloomington. Friday night traffic and all that. My heart was pounding the whole way. This couple was a lot of fun to play with, and we’d connected well through conversation too. No matter what, I could expect a fulfilling night with them.

I got to their place a few minutes before them, which I’m sure made me seem as eager as I felt. They pulled in, still in the midst of laughing as they got out of the car. Definitely talking about Sean. Mike let us all in, and as we made our way to the bedroom (straight there after the shoes came off, no time wasted in the foyer or living room), Britt told me she’d gotten a text from Sean during their drive back. She showed me. It was, seriously, just this: :(

Sex, Drugs, and a Craigslist Swinger Party [group]

A few years ago I was dating a lovely young woman, for the sake of this story, we will call her Carolyn. She was my ex’s best friend. It was never said beforehand, but we knew we had chemistry. Needless to say, when things ended with my ex, Carolyn swooped in and claimed me for her own. I definitely wasn’t complaining. Carolyn was definitely petite, coming in at 5 foot 2 inches, 95lbs. The thing that got me was her 28H breasts and the tightest, tiniest pus1sy I’ve ever experienced. She was a goddess and little did I know she was a freak too.

Once during the my ex, she told me a story about her and Carolyn getting drunk together in the hot tub. According to my ex, Carolyn started asking ‘weird questions’.

“Don’t you think girls’ bodies are so sexy?” Followed shortly after by, “Have you ever considered being with a girl?”

After more of these questions, my ex got a little nervous. She then felt a hand on her inner thigh. She didn’t know what to do, so she started talking about something trivial. As she talked, the hand moved up her thigh and under her swimsuit and began rubbing her clit. My ex-girlfriend freaked out, got up, and left, and she and Carolyn never spoke of it again.

A quick pre-convention drop-in for pleasure [FM]

Now that it’s summer I’ve got a fair few events that I’ll be heading to in cosplay, and this weekend was one them. I’m currently back at home now uni was finished, so what would previously have been a reasonably local event saw me jamming some cosplay into a case, jumping on a train and heading to a cheap hotel near the event for a few days.

Although I knew a fair number of people there to hang out with, none of my direct friends came along to share hotel costs so I was left to my own devices for the duration – of course, this in turn gave me plenty of time to seek out new adventures. The first day of the event was pretty dead however – as it was located somewhat out of the way most people were at work and there didn’t seem to be anyone from the event on Tinder, so it was a fruitless evening’s swiping. The second day brought a fair few matches, but nothing interesting – a lot of outright idiots, or conversations that just drifted away into nothingness.

Secretly Fingered GF While Streaming [MF] [hold the moan]

I must have been the most sexually aloof guy during high school. Far from prude, I just never treated sex and relationships as a priority. I barely spoke a word in classes, let alone tried to flirt, and the only way I caught onto the fact that a girl I shared the bus with for 3 years liked me was when she literally placed her hand on my crotch. Even still, I ignored her. Yeah, I was **that** distracted.

That’s what made Kris a special girl. I mentioned her before as a bubbly video game streamer with multi-colored hair and tats who shook up my strict, rigid world at age 23. As social as she was on her stream, she wasn’t the typical camgirl flirt. She took her first-person shooters seriously, childishly laughing at the explosions, and ignored the compliments poured on her by her viewers.

[MF,fm] Julie and the kids [not much sex, but voy., mast. and ‘sextortion’] Part 3

I ordered the smoke detectors with integrated wifi spy cameras the next day. It’s something I had seen online before, but never had a use for…until now. I ended up getting four of them, one each for my bedroom, the guestroom where all three were staying, as well as the bathroom, plus one extra in case I found another use for it.

I paid the extra $29 for express shipping, even though I might not have time to install them until the weekend. Things at work were pretty busy, not leaving me much free time during the day to start installing these things.

We got into somewhat of a routine over the next two days. Julie got the kids ready for school, and we all went in my car to drop them off, and later to pick them up. She and I were home during the day, but because I was busy with actual work, she just loafed around watching TV with nothing else to do.

Julie’s did get called in for one shift in the evening. The kids would be home with me “babysitting” them. I said it was fine, that she needed the money. I even let her use my car that night so she wouldn’t have to figure out how to get back at midnight via cab or bus.

[MF,fm] Julie and the kids [not much sex, but voy., mast. and ‘sextortion’] Part 2

The next morning I was down stairs making coffee when I heard footsteps upstairs in the guest room. Once it was apparent that they were all awake, i called up to them to come down for breakfast if they’d like.

Shane and Taylor came down first. They were both wearing shorts and a large tee shirt. I got them some cereal and juice (not a whole lot of breakfast options in my house). Julie was still upstairs getting dressed so i got to spend a little time with the kids. They weren’t very talkative, but at least told me what grade they were each in (4th and 6th) and which school they went to.

Julie came down and thanked for helping feed the kids. She said that she had been able to get her cell phone turned on and get to the address book to get some phone numbers, even though her service was disconnected. She had used my upstairs phone and said that a friend was coming by in 20 minutes to take the kids to school.

The kids got dressed in the same clothes that they had been wearing the day prior and went outside to meet the friend.

[MF,fm] Julie and the kids [not much sex, but voy., mast. and ‘sextortion’] Part 1

Please leave a comment if you like this. Happy to get story ideas as well (in similar vein as this.)

Fiction

***
Julie and the kids.

As I sat at kitchen table surfing the web with the baseball game playing on the living room TV, I heard the first shouts between a man and a woman. I live in a semi-rural area, and have a 1/4 mile long driveway, so I don’t get too many unexpected visitors. Plus, it was raining outside pretty hard.

I walked to the door and looked outside. There was a tow truck driver just down my driveway a bit getting into a heated argument with a lady in a beat-up late ’80s station wagon.

I grabbed my coat and headed outside to see what this argument was about, and more importantly, why it was happening on my driveway.

As I got closer, I could hear what they were saying:

“Lady, look at the paperwork, it’s right here. You owe the money.”

“But I called last week and they said it was ok to make smaller payments.”

[MFm] [mast, some sex] Josh’s Girlfriend

Fiction, of course. Please let me know what you think.

***

My name is Ethan. My brother Josh was 8 years older than me, and mostly because of that age difference, we weren’t particularly close when we were younger. He was my only sibling. Mom and dad were pretty normal, I suppose, but they were both college professors and I think were more aloof than parents of other kids my age. They were loving, but just never seemed overly interesting my our lives – perhaps other than how well our grades were.

When I was 15 and a freshman in high school, my parents enrolled me in a private school about 45 minutes away from home. Most of the kids at school were boarding students, but about 30 of us just attended during the day and returned home every evening.

Josh was 23 and already living alone in an apartment by this time, and in the same town as my school was located.

Fun in the Philippines part 1 [MFF] / [MFMF]

Warning, very long and detailed. Tl;dr; wifey and I had an amazing evening with a lovely new girl friend and one of her swinger buddies. Pictures are at http://imgur.com/a/kORgR

Wifey and I spent a couple of weeks together in her home country, the Philippines. We had an amazing time, lots of great sex, went to islands, snorkeling, diving, sea kayaking, awesome fun! The last evening in Manila was also a great time.

We met our new friend Irene through a swinger website called TheAdultHub. I have to admit that we never used it much, I think I subscribed to it a few years ago but never really looked at it. But recently I got an email reminding me about this site, so I thought why not try it and I subscribed to the paid tier. This allowed me to answer a few message and send a few more, amongst which Irene’s profile caught my attention.