Tag: Girlfriend

How my friend’s girlfriend made me [M] squirt for the first time (UPDATE)

[Link to the first post.](https://www.reddit.com/r/gonewildstories/comments/ny5gcx/how_my_friends_girlfriend_made_me_m_squirt_for/) TLDR: Recently got out of a relationship. Close friends who are a couple thought it would be fun if she tested her handjob skills on another male. Boyfriend watched while his girlfriend made me squirt cum in clear droplets like a garden hose.

Since then, I couldn’t stop thinking about what happened and have tried on multiple occasions to repeat it solo. Needless to say, I failed miserably. Pulling back my foreskin and stimulation just the head was just too sensitive and did not feel at all like what Lisa did to me. After several failed attempts, I lost patience and reverted back to regular masturbation.

As I mentioned in my last post, Jake and Lisa were super cool about the whole thing and I get the feeling they were even enjoying it. While most of our friends were away for the break, I ended up staying on for a summer internship. Lisa also stayed for a couple of weeks to help out with one of the university clubs while Jake had already left. Read more »

An at-home happy ending [MF]

This is my first attempt at posting on any of these subs, but my saint of a girlfriend has been planning something extra slutty for me for Father’s Day and I know posting this story for all to see will be a great way to kick off whatever she has planned!

Happy Father’s Day!
—————————————————————

If you’ve got a penis, and you’ve gotten a handjob to completion, you know how wonderful they can be. Unfortunately for most of us we’ve all been beating our meat so often for so long that it takes more than just a few lubed up-downs on ye olde donger to get off. Even then, some handjobs can feel dissatisfying, leaving you drained yes, but ultimately *unfulfilled*. But if you’ve ever had a mind blowing handjob… a real “I saw the eyes of God and he is CUM” moment, you know what I’m talking about.

You never forget those handjobs.

My girlfriend Annie and I have been all but inseparable since we began dating. She’s 21, tiny (ex-cheerleader), about 5’5” with shoulder length brown hair, and the biggest most beautiful brown doe eyes you ever did see. Her assets – B cups (my fucking **favorite**) and an ass that just will not quit… good god I love her ass. The first time I saw her I was literally *stunned*. Read more »

I 32[m] fucked my Girlfriend [f] 29 in a closet at a wedding. She creamed all over my dick.

My lady (let’s call her Sky) and I hadn’t been out much since the covid lock downs started in 2020, our relationship was built off of outdoor adventures. So, when a chance to fly to Pennsylvania to get all dress up to attend her cousins wedding arose, we jumped on it.

We had yet to see each other cleaned up for a formal event, she looked, absolutely stunning. The pictures of her in her green flowing dress gives me chills to this day. The no shit sparkle in her eyes that night and the smile she wore makes my heart melt and my cock start to flush with blood. I couldn’t be more in love.I looked like a perfect gentleman, I wore a three piece suit custom tailored to me, a new semi expensive watch and a nicely trimmed beard.

We were staying at an Airbnb with her mom and aunt. We also all drove to the wedding together as well. As the wedding started there was the usual formality’s an open bar and a lot of dancing. Read more »

Sicilian Seduction [MF]

I’ve been spending some time in Italy, got my own place, visiting old family friends in a small town. Everyday I wake up and walk to the town square, have some coffee and a bite before going for a swim. Today I get up a little late, having drunk a bit more than usual the night before, and for once there are people already laid out on my favorite slabs of stone. Except for one man with his girlfriend, I’m the only guy there (though gender isn’t dreadfully important to me. Can anyone without raging insecurities look in the mirror and say ‘I am a MAN’ without feeling silly?). Maybe a dozen women sunbathing, no one actually swimming.
I go to a higher rock than usual and stretch out, only realizing during downward dog that one of the girls on my right is not laying down anymore, but resting on her hands, and while we both wore sunglasses the angles of our face made it clear she’d been busted staring at me. She quickly looks away.
“Ciao” I say, stopping my stretch and sitting on the edge of my rock, legs dangling over hers.
“Ciao”, she smiles, “come va?”
“Sorry- I’ve just gotten here, not sure what that means.”
“Ah!” At my English her friends all perked up, all maybe 2-4 years younger than me. She had the strongest English of the lot, though charmingly unsure of herself, “We from this place. And where are… you from?” Read more »

That time I ended up having a threeway with two strangers while on vacation. [MFM]

This happened about two years ago when the world was still open and one could travel freely. 

I (25,M) was on vacation in Vancouver, and single as all hell. I was in the city for about a week, and I really wanted to share an experience with someone. Shortly after arriving, I went to my airbnb, freshened up and hit the down. I did a bit of a bar crawl; went to some cool dive bars/grungy performance halls, and met quite a few cool locals. 

At one of the bars, I saw this gorgeous brunette. She was standing at the bar waiting to order. I decided to grab myself another drink, and shoot my shot.

 She was in a stylishly ripped white t-shirt, a red bra that you could see through the rips, tight black leather pants, a tight bubble butt, what appeared to be DD tits, and an overall body type that screamed fitness. Read more »

[M]y First [F]WB Made Me Cum in My Boxers, Pt 4: I Think I Got Cucked?

I’ve gotten a handful of requests to continue this story, so I’m happy to share the next part of my premature adventures with Haley. As I mentioned in [my last post](https://www.reddit.com/r/gonewildstories/comments/nq3two/my_first_fwb_made_me_cum_in_my_boxers_pt_3_how/), Haley and I began dating other people off and on after those initial set of stories, so our meet-ups became less frequent. However, when we were both single at the same time, we inevitably started hanging out and hooking up again, and this next part takes place during that period when we were in between partners.

As always, to recap who I and Haley are, I’m Tyler. Currently 31, but an 18yo high school senior at this point. I was a late bloomer; a bit chubby until I grew into my height (6’2), and then became pretty tall and lanky. My cock is slightly above average size-wise (6.5 to 7″ if I’m really feeling it!), though I had no idea at the time that I was above average. I played baseball and was in decent shape, though the years of social awkwardness and not seeing myself as attractive had left me pretty unexperienced; I had kissed a girl, but never gotten past first base at this point. Until I started talking to Haley. Read more »

My (23F) first girl-girl sex in over a year was sooooo gooooooooood ??? [FF]

So last week, my friend Kat calls me up and asks if I want to come over and go out with her that night. She lives close to downtown, so I’d be sleeping over at her place before coming back home here to the suburbs the next day. Kat’s just a girlfriend, but we’ve also hooked up plenty of times in the past. So I wasn’t sure if this meant we’d be finding some guys or leaving them behind. Either way, I said “OBVIOUSLY” because I’m itching to get out again.

Kat is gorgeous. Curly dark brown hair, about shoulder-length (shorter than mine). She’s petite, just 5’2, with these big green eyes. She is “straight” to everyone but a couple of us who have known her for a while. Almost none of the guys she dates knows that she has a deep love for girl sex too. But… omg, does she know her way around eating pussy. Read more »

Seduced by his friends Mom [MF]

It had been a nice spring day. Overcast admittedly, but it was dry and reasonably warm. Without giving it much thought, Jordan had made the decision to wear just a t-shirt and jeans for the walk across town. It looked like a fucking stupid decision now – the sky had opened suddenly just a minute ago and it was pouring rain.

Jordan was on his way over to his friend Dave’s house to drop off some money he owed him. He was closer to Dave’s house but it was still a good ten minute walk away. Still, he thought, he could wait out the shower there and Dave would probably drive him home…. As long as Dave was home. Swearing under his breath, Jordan broke into a run.

Five minutes later, feeling thoroughly miserable, Jordan arrived at the house. His heart sank when he saw Dave’s car was missing from the driveway. He was probably out. Fuck it. Huddling under the doorway, Jordan rang the doorbell and prayed Dave was home. After a minute, the door opened and Sheila was standing there. Read more »

When I was at university, I signed a no limits free-use contract with a guy I barely knew… [FM]

I was halfway through my freshman year when I heard about him.

His name was Jack, and he was the sort of guy you’re always told to keep away from as a fresher. Big. Misogynistic. Disrespectful. His dad was some sort of high-flying banker, and he never seemed to suffer any consequences from his actions. There were rumors that he’d raped girls. I heard he’d had a girlfriend in his second year who kept showing up with bruises – the sort she hadn’t consented to. I was warned to stay away from his frat house – especially when they were having a party.

He was dangerous. Scary. And I wanted him.

By that point, I’d had an idea knocking around for a while. The notion of a free use contract. The sort that would give up my rights for 24 hours, and make it clear a guy could do whatever he wanted to me. And once I’d heard about Jack I couldn’t get it out of my head.

When I was young, I had always been fascinated by the idea of giving up my rights. I’d heard about the saner sorts of BDSM – with safewords and negotiation, the kind where you submit to someone you trust. But I wanted something more intense than that. Read more »

Learning to Share [Part 1]

This story is a custom request, as well as a re-upload since I had a problem with my previous account. This is the first story I’ve ever written, please let me know what you think!

-Alena

<—–>

Liz felt incredibly frustrated at herself as she dashed across the parking lot from her car to her boyfriend’s apartment complex.
Her boss had told her weeks ago about the seasonal reports that were mandatory for her department. He had sent emails, posted reminders, and nagged her to death and she somehow still forgot them. They had to be submitted by 12:00 AM Saturday- which was today.

As Liz pressed the elevator call button repeatedly she checked her phone.

11:38, I can still make it! All I have to do is send the email and It’ll be fine!

The assignment had simply slipped her mind until a few hours ago, luckily she had it completed and loaded to a thumb drive, she just needed to submit it and she was safe. The only problem was that she had left her laptop at work on Friday.

“I’m so stupid! Why did I wait this long?” Liz muttered as she stepped into the thankfully-empty elevator, selecting the correct floor. Read more »