Tag: Girlfriend

Orgasm in front of girlfriend’s unknowing dad[MF]

Some people asked me to tell about the relationship I had with a married woman, and I’m sure I will at some point, but I do still have some guilt over being an adulterer (we just decided to try to chill out two months ago). Plus, to be perfectly honest, it’s a very, very long story for me to describe correctly. Hope you don’t mind me instead describing a quickie I had with a girl my age (I do sleep with “age appropriate” girls, too!).

If you do want to read about my first time with an older woman though, you can check it out [here (pt 1)](https://www.reddit.com/r/gonewildstories/comments/598ol8/late_40s_f_and_the_college_boy_m_a_first_for_both/](https://www.reddit.com/r/gonewildstories/comments/59xwkg/late_40s_f_and_the_college_boy_m_a_first_for_both/):

To just start with a little background, I was a tall, gawky kid growing up, with glasses and an overbite. Then I wrestled throughout high school, got contacts, and dental work fixed my alignment to where I’m actually a pretty good looking guy (I’m told I look like the senior in Sixteen Candles), but I still have the perception of myself as a gawky kid with glasses and can still be somewhat shy until engaged and alternate between overconfidence and no confidence. Read more »

[M]y [[F]irst time creampieing an asshole

Hey guys. First time posting so I’ll try my best to layout the story that happened to me last year.

A little background first. I’m a 20 y/o male college student. Been with about 16 women in my life, have only done anal a handful of times with 3 different girls and let me tell you, it’s the greatest. This was not only my first time cumming in an assh, but also the hardest orgasm I’ve ever had. Okay so let’s get on with the story’s

I had recently broke up with what I was convinced the love of my life. So as devastated as I was, I was looking for anything to make me forget her. So I did what any young college student would do to get over a heartbreak, download Tinder. I went through a couple girls thing exciting or worth messing with until I came across Star (not her real name) Read more »

The Gift of a Warm Mouth – [MF]

I was at a training in a city far from home. I hadn’t seen Stacy in weeks, but we spoke almost every night and every day my cell phone would bing with her nude photos, sent to cheer me up.

Then, midway through the day, she sent me a text.

“I have a surprise for you tonight.”

“What?” I wrote back.

“It’s a surprise stupid,” she just said.

I waited in anticipation all day long as she teased me. She asked me to guess.

-Extra dirty photos?

“No and I don’t know how you expect me to send you dirtier ones.” This was accompanied by her, clearly at her work desk with one leg over the arm of her chair, her bare pussy and ass visible up her skirt and a pen in her asshole.

-I hope your not sending that pen via courier.

“Nope!”

-Phone sex?

“Boring!”

-Cam sex?

“Wrong again lover, you suck at this game.”

It went on and on. My guesses getting increasingly bizarre, I believe I asked if it was a life sized sex doll made to look just like her. Read more »

Pills, Part 4 [MFF][Bimbo][Light Sub/Dom]

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Pills, Part 4
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“Here, honey.” Rachel said as she handed my cum-soaked lover a clean white towel. “I hope you don’t mind, Jack. I found them in your bathroom while you two were – um – distracted. Here’s one for you, too.”

Rachel was offputtingly capable of maintaining eye contact as she handed me the cloth. My deep blue robe had been opened to provide my bimbo-fied girlfriend full access to my inflated cock, towering roughly a foot over my chiseled waist. An obscene amount of cum had been pumped from my heavy balls onto the couch, coating Ash with a pearlescent glaze in the process. Rachel had been binging on Crisps over the past two weeks, though, so I understood how she may had become desensitized to such lewd displays.

I did not have the same composure. Although I had just produced more cum than any man should be capable of, my dick refused to sag. The capstone of my shaft continued to ooze clear liquid, while my eyes darted between Ash cleaning her massive tits and her fat dripping lips. My mind raced with the endless ways I could use her now that she had become a submissive sex doll. My body was slowly becoming pressurized with the need to fuck and I simply couldn’t seem to snap out it. Read more »

[MF] True story, a tough nut to crack, a shy conservative asian girlfriend with a banging body who has potential.

We don’t “sit down and talk” about it. That’s not how it works between us.

That’s why, by “encouraging her”, I mean, going for the intricate mating dance, where the partners read each other’s body language and pick up on subtle hints to deliver the ultimate experience.

When it works out, it’s amazing. So, “just ask her” and “tell her what you want” isn’t gonna work between us. Every couple communicates in their own ways. And this is how we communicate. Innuendos. That’s what makes our relationship hot, exciting, special and always new. And I believe that’s how nearly all women communicate, from my experience. In certain situations, you can’t just tell women what you want in a blatant way and expect her to do it. One of the things women hate is ‘men asking shit’. Like, can I grab your boobs? Can I kiss you? In their mind it’s going “Gross. I’m gonna feel guilty and if I say yes. Why the fuck are you even asking? Just fucking kiss already.” These are the reasons why Rape Fantasy is very common among women. Guilt free. No need to take accountability for what happened. Read more »

Vetting our third before the big event. Gf got a closer look than me [mfm]

The date had been set. 6:30pm at the bar patio. The initial approval of physical attractiveness from photos and some casual conversation over text led to the next step: meeting for drinks. This would let us get a feel for the guy and ultimately decide if we wanted to have our threesome with him.

Jenny met me outside my office building after work. She was wearing a tight grey dress that showed off her ass beautifully and a real bra to put her tits on display as well. She had straightened her hair and done her makeup as well. Her aviator Ray-Bans completed the movie star look. All in all, she looked hot. So hot, I knew this guy was going to take one look at her and know he wants to fuck her. It was just up to us to see if we liked him. Read more »

[MF] First AOL Meeting, First 20-something, First Contact, First Puddle (very long)

(If you want to skip straight to the sex, scroll down to the first break. This is a long one.)

Back in the late 90s, I thought I was a god on the nascent internet. I hung out in all the right AOL chatrooms, visited all the right websites, and sysop’d all the right BBSes in my local area. I was 18, and I’d been reading erotica text files and hosting pornographic pictures on my own BBS for years already. That plus some built-in predilections led me to know that I was into spanking.

I also didn’t have a ton of friends at college. My roommate was cool, and there were some other folks I hung out with, but by and large I spent most of my time online. And, as you did with AOL back in those days, you would see people come into a chatroom, you’d check their profile, and you’d send them a message, hoping to start a conversation.

Even back then I’d learned from other women on my local BBSes that men online were generally assholes who only asked “A/S/L” (kids, ask your parents) and treated women like crap. I tried not to be that way, and I guess it worked, because one October evening I clicked on a profile that interested me, said hello, and struck up a conversation. Read more »

[MMF] (mild story) My girlfriend stepped up her exobitionist side.

So i’ve got a mild story for you guys, but to me it was a lot of fun. Short background before the story, I (M, 21) went on a weekend trip with my whole family, including my girlfriend (F, 20) and my cousin (M, 18) we rented a big house, with a whole spa, including a jacuzzi. I’m also very close with my cousin, and my girl has an exobitionist side, but still kinda in the closet . So, to the exiting part. We went around 11pm in the jacuzzi, me, my girlfriend and my cousin. My brother went along also, but got out and left shortly after. The half of my family was asleep and we knew we weren’t goint to be bothered now. So at this point, we are in the hot tub, the room was dark, with just some cosy lights on, casually speaking about chitchat with my cousin, and al of the sudden i notice her shoulder straps are gone, so i ask her “where is your top?” And she replies saying it’s to hot to wear them. Her breasts weren’t really visible, since it was dark and they were submerged, but my cousin really got exited obvious. I really liked that my girl was topless among my friend, and never thought she dared to do this,i went next to her, subtle groping her breasts and still talking with my cousin, he didn’t mind the circumstances at all. My girl even went further, changing her seat, and exposing her breasts fully to him while doing so, sitting in my lap so i could grope her tits in sight of him, and just sitting there, boobs above water level so he could stare as much as he wanted. After all this it was around 2.30 am, and we eventually got tired and went to bed to. For my girlfriend this was really sonething new, and i’m still to this day amazed that she dared something like this! Thanks for reading guys, sorry for any grammar faults.

My [F] insufferable tease [M] returns. But at least I felt inspired again.

*Sigh* I did the thing. I alternate between hating this insufferable tease, to wishing with the power of 80’s children’s movies that I could cum in his mouth over and over again. I don’t hate him for any reason other than my own obsession with him being responsible for my orgasms. It’s infuriating. I don’t chase boys… I’m chasing this boy, and he’s a bad boy. I wants it, like Smeegle. My precious. The real problem is he knows I want it, and it brings him no small amount of pleasure to deny me a solid, lengthy fuck. Tonight I texted my subs to get my corset cinched up before a house party… I was running out of time, I needed to get tight-laced immediately. I text Cold War and ask if he’d like to make $20 to cinch me up so I can get my Dominatrix outfit together and stomp the yard at a haunted house party. I didn’t expect him to answer, but I was hoping the Jew in him would find the motivation to not flake out on me for that $20. It worked. I offered to pick him up, but he said he’d just come over on his own. I assumed cab, whatever- I need to shower quickly. I figure I’ll drop him off on my way to the party, so I’ll stop by an ATM on the way. Simple, right? Read more »

[MFF] threesome with 2 barely legal redditors

earlier this year, as i was getting ready to celebrate my 40th birthday, with an attractive, but strictly vanilla school teacher girlfriend, and knowing i was going to receive yet another basic, half-assed, blowjob plus strictly vaniila, missionary sex, something inside me snapped and that was when i decided this was going to end. i was still going to enjoy the brazillian steak house and vanilla sex that night, but it had to end soon.

me: straight, hung, mixed latino, dark curly hair, full beard, smiling eyes and plenty of stamina.

so that was that… approx 4 weeks later, i had ended that relationship and started answering posts from female redditors requesting sexual contact. i realize that many guys on here never receive a reply, but knowing how to engage women IRL helps alot. suffice it to say that my 3rd successful reddit hookup was exactly 10 weeks after the previously described birthday dinner. the woman i met that night was a female who had turned 18 just a few weeks earlier. she is called pink in this story. after verifying her age for me, it was on, but i have posted a RAOMD success story about her already so i will move on and simply say that we had a great hookup which lasted 14+ hours, with countless orgasms for her and 5 full effort fuck sessions from me. i was hooked! Read more »