FWB Loves Anal [MF]

“Daddy, PLEASE fuck my ass!” Grace pleaded.

She and I had anal sex for the first last spring. Her last boyfriend wasn’t too interested in it, so I was really the first person she explored it with. Turns out she LOVES it! She’s tall (5’10”), skinny but with a nicely shaped ass from years of competitive swimming. Her long brown hair is usually in a ponytail. Grace has a smile that will light up a room, and eyes that are so blue you want to swim in them.

Personally I’m going for the sexy Dad next door vibe, although it feels like I forget the sexy part sometimes. I’m tall(ish), stocky, more salt than pepper in my hair these days. I’ve been told on more than one occasion that my cock is a great size for anal. Not too big at close to 6”, with a good girth. Additionally when I get hard, it’s HARD.

We were trying to ease our way back into bedroom activities after a six month break. The emphasis should be on “trying” though as we were attacking each other the way a Survivor contestant dives head first into an all you can eat buffet! I’d already spent 30-45 minutes eating her pussy; we’d gone through our favorite positions, I’d even shackled her and gave her a few licks with the whip.

Fucking A Redditor Half My Age! [MF] (part 1)

“So you’ve never had your pussy eaten?” I asked Maddie.

“Never” came her quick response.

I was incredulous.

Maddie had reached out to me on Reddit a few days before coffee. She had seen my recent post of pics with my FWB and found the arrangement appealing. We chatted off & on for a few days before I offered to meet for coffee. It was the logical next step if we were going to work our way towards checking off items from her sexual bucket list. Our conversation over kik had been mostly about sex, so it was a little strange to be seated on a coffee shop patio making small talk. Still we flowed from topic to topic with ease.

At 24, her sexual experience was surprisingly limited in some areas. I couldn’t believe that no one has ever gone down on her. On the tall side at 5’9”, she falls into the cute & curvy category. Her dark hair was pulled back in a high ponytail, her outfit was casual and comfy. Kinda like her.

I’m 50, tall, Dad next door looks with more salt than pepper in my hair & beard. I blame my children. ;-)

“Are you going to write about this on reddit?” Yes. Yes, I am. [MF]

We walked back to her car, holding hands, fingers intertwined. The conversation over drinks had been easy, fun and flirtatious. At one point my hand had brushed her leg by accident, but I noticed a slight shift toward me so I intentionally put it back. Kat’s smile still held sway over my attention. This was our second date in twice as many days, and I was glad for it. My original dinner plans would’ve had me spending time with someone else, but that was cancelled a few hours before meeting. 

“Let me feed the kids, and I’ll meet you for a drink around 7:30” she messaged when I told her of the cancellation.

“Hell yeah! I’ll see you then!”

Her car was parked in a covered garage around the corner. LIke a pair of teenagers, we started kissing as soon as we got there. I pinned her up against the vehicle with my body, holding her hair in my right while my left roamed up and down her body. We could hear another couple saying good night and going their separate ways. 

Fucking A Redditor in a Public Restroom [MF]

If you’re keeping track at home, I recently tested an FWB arrangement with an ex (here & here). Well… the “friends” part of that equation is working out, but it looks like the “benefits” are on indefinite hold. Such is life. 

A few days after posting last week I got a message on Reddit, our chat started like this:

“I feel like we should be friends.” – What a great way to start a conversation!

Me being me, my phone was nearby so I answered pretty quickly; “Why is that? I’m always open to new friends!”

“Lol I saw one of your comments about cheating in the military and noticed you were from Austin too. I like big personalities”

My Ex Became My FWB [MF]

The full version of [part 1](https://www.reddit.com/r/gonewildstories/comments/it8f2o/whats_a_little_bondage_between_friends_or_how_my/).

Here’s the short recap: Grace and I were dating in the spring, but broke up in May. We’d explored the idea of casually dating, but nothing came of it. I invited her over for pizza, where she brought up my previous suggestion of trying an FWB arrangement. Before proceeding with the Benefits portion of the evening, she had a little punishment to work off in the form of bondage and whipping. Ok, so it wasn’t REALLY punishment ;-)

Seriously, read part 1 if you haven’t already.

…………………………

After ending the scene, Grace started kissing me. I had missed those lips and couldn’t hold back. I tried putting four months of wanting her into those initial moments. I know we were going to leave as much emotion out of the evening, but this was my chance to tell her how much I had missed her without words. We were never going back to that emotional precipice, I was never going to speak those words again, but I wanted her to feel it in my kiss at that moment.

What’s a little bondage between friends? Or how my pizza got me laid [MF]

Grace’s eyes got as large as saucers when I showed her the lighter. At this point, there wasn’t anything she could do about it since she was restrained with her hands in cuffs over her head and secured to the door jam. The ball gag was secure in her mouth, allowing her to breath, but any vocalizations were more grunts and moans than coherent words. She had two choices: flash me the ALL STOP hand sign that we had agreed upon, or trust me.

I should probably give you a little background behind Grace and I so that you understand what led us to this point.

I met Grace online at the end of January (2020). At this point, Covid-19 was just something on the news that China was trying to control. Initially our relationship was based on sex, we were both looking for something fun and exploratory. She’s 28 years my junior, but it rarely felt that way between us. We just worked.

My First Visit to a Glory Hole [MF]

More than a few years ago, I answered a craigslist ad from an escort that was offering a gloryhole service at a good price. I’m naturally on the cheap side, although I prefer the term “frugal”, and this extended to paying for sex. The ad said that she would have a glory hole curtain set up, with a willing participant behind the curtain. The host (who placed the ad) would be on the outside with the customer to manage the experience. 

For those unfamiliar with the term “glory hole”, it refers to a man sticking his dick through a hole so that an unknown and unseen person can service him. Usually this refers to oral sex, but it can also mean intercourse. 

Back to the story.. I arrived at the address I was given, it was surprisingly in a quiet suburban neighborhood in NE Austin. If the neighbors only knew what was going on in that house! Lori answered the door wearing a robe. I’d describe her as more than cute, maybe pretty when she was dressed up. Probably 5’5”, long brunette hair (I have a thing for brunettes), moderately sized boobs (I’d guess a b cup but I’m a guy… we really don’t know these things!), thick thighs like she used to be a gymnast, nice firm ass, and a sexy smile that instantly made you feel welcome.  

The MIL[F] that thanked me for [M]y service!

I was 20 years old in July 1991, a few weeks shy of my 21st birthday. Tall and lean. Worldly for a 20 year old but still pretty young looking back on it now. My hair was cropped short, my smile was easy and engaging. I’d been stationed in Germany with the Army for three years and was used to German bars, nightlife, and women.

I was back in Texas on leave, having been deployed for the previous 6 months to the middle east for Desert Shield & Desert Storm. I fought that short war from the turret of a tank, and was ready to forget the Army for a while. My Dad and I were heading to the coast to go fishing but stopped in Austin for the night.

Austin in the early 90’s wasn’t the robust city it is today, instead it was a sleepy little college town. Most of the residents seemed to work for the state or the university. There was only a single bar district, 6th Street. We stayed at the Sheraton a few blocks north of 6th, easy walking distance (this was LONG before the days of Uber & pedicabs).

I Gave Him A Facial While His GF Blew Me [MFM]

A few years ago I went through an experimental phase where I explored my interest in having sex with men. To be honest, it was really just because it’s easier to find a guy to blow you in the middle of the day than a willing woman. Guys are just slutty like that. Closeted bi guys are ESPECIALLY slutty like that. You wouldn’t believe the number of ads that get posted by men who are living otherwise very straight lives, but enjoy sucking a stranger’s cock.

I had previously answered an ad from Tom. He wanted to perform oral on a guy, and had access to his girlfriend’s apartment. The short version of that encounter is that he gave me the worst blow job I’ve ever had; there was a lot of tugging, pulling, not enough suction. It was horrible, but how do you tell someone that they’re doing a horrible job while your dick is in their mouth? I forced myself to cum as quick as possible just to extricate myself from the situation, happy to leave the experience in the bin of bad decisions.

Was this a threesome? [Group] [MMM]

When thinking about writing about this event, I became a little unsure if I should share it. I’ve never discussed my bisexuality in public before, and I’m old enough to remember the stigma that being gay has meant for so many men of my generation and before. Even now I want to preface this with “But I prefer women…” as if that’s anyone’s business. Anyway, this is a story from an experimental period I went through a few years ago. It’s purely guy-on-guy-on-guy. Enjoy.

I answered an ad on doublelist from a guy that wanted to watch another man masturbate. I figured why not? Having an audience is fun. He replied quickly, starting the typical dialogue for these types of things. His place was on my way to work, and I could spare the time that morning, so I agreed to stop by. There wasn’t really a promise of anything more than me stroking for him, but I was ok with that. Masturbation is fun!