Category: gonewildstories

I [M] fucked my first mil[f]

My first ever milf

So a couple of months ago i had my first sexual experience with a milf!

We matched on tinder, she had one of those profiles without any real pictures, but her bio said; “in need of some decent sex” so i swiped right and we started talking…
Didn’t take long before the conversation was about sex. She told me she was into kink and bondage and stuff.. i invited her over to have a night of drinking and fucking (at this point i had NOT seen her face yet ?)

When she arrived at my place, there was immediate relief as she was a really beautifull woman! She didn’t have big tits (wich i usually love) but her perfect ass made up for that!

So we started drinking and talking, eventually she came sit right next to me. Honestly i was NERVOUS AS FUCK!! She leaned in to kiss me, we started making out and after a few minutes of making out she asked me to take her to my bedroom. Read more »

[M] First time with an escort [F]

I’ve been looking for awhile and finally took the plunge yesterday. Found one I liked with good reviews so I texted her. She’s also active on Twitter and OnlyFasn so i figured she wont murder or rob me but its still risky of course. She asked me a few questions then called me. Donation was a couple hundo for the hour. Got to her house which was her Aunts house she told me as she kids were at her house. She is 29 and im a 40 yr old guy. She literally answered the door in her bra and underwear and mind you its a good sized city in Western NY and about 6pm but no neighbors were out.

I walk in and hear people in the kitchen. Nervous now even more lol. We go into a small darkish room with a bed and lamp and that’s it. She gets naked and lays on the bed. We talk for a minute then she puts my hand on her pussy. Now when I texted her, she said she doesn’t talk specifics on what she offers but I’ll be satisfied. I read on various websites she gives the best uncovered BJ’s and likes anal so im not worried I won’t have fun. Read more »

45 [F] cougar fucked in parking garage by dream boy toy 21 [M], thwarts covid cock block

If I were to head into my cougar lab and design the perfect boy toy (think Dr. Frank N. Furter and Rocky Horror), I’d have spun John right out of a centrifuge. 6’1, with brown curly locks cascading into sparkly brown eyes. Killer smile, with corresponding dimples. Athletic body adorned by washboard abs. It’s gross, I can’t even.

John and I met online (through tinder) weeks after the pandemic landed in Ohio, and shortly before his college returned him home out of state. Thus began a torturous four months long tease, with me hoping (nay, praying) college would return him to Cleveland.

So when he asked me, “are you free today?” all I could think about was resolving this antici…
…pation. We agreed to meet at the Botanical Gardens and walk around, seemingly innocent enough. Maybe people would think I was his favorite Aunt, or maybe even his Mom, if my body language didn’t betray my ill intentions. I think the truth is, most people don’t “think” anything about perfect strangers they see, and certainly don’t assume the worst about them. Read more »

I [23 M] fucked a married mil[f] at my internship.

This happened last year, when I was 22.

I accepted an internship at a pretty big company, knowing it would look fantastic on my resume. From my first interview, I had already had my eyes on the secretary, a gorgeous early to mid-40’s Filipina. Everyday when I walked in, I always initiated conversation, and she was very friendly with me. However, after a few weeks, I decided to start subtly flirting with her. To my surprise, she flirted back (wasn’t very subtle) and after 2-3 days she invited me to get a drink with her after work, on a Friday.

Fast-forward to that Friday. After getting off work, we both head to the bar as planned. We sit down, order a drink, and really start talking. There was definitely already some tension at this point, and I couldn’t stop staring at her cleavage with those incredible 32 F boobs. After about 30 minutes of chatting, she cuts straight to it. Tells me to cut the BS, and if I want to fuck her we can go to her house 15 minutes away, her husband was out of town. Her straightforwardness surprised me, as I hadn’t ever experienced a woman being so straightforward. I fumbled over my words to her amusement, before we both agreed to drive to her house. Read more »

How the Spontaneous Friend-Cation turned into the Fuck I Never Expected: Pt. 3 [FM]

[part 1 ](https://www.reddit.com/r/gonewildstories/comments/ij7czl/how_the_spontaneous_friendcation_turned_into_the/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

[part 2](https://www.reddit.com/r/gonewildstories/comments/ijh8u2/how_the_spontaneous_friendcation_turned_into_the/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

Ok, third and what I expect to be the final part of this story. Again, thank you all for the kind words and messages. Some of them are extra appreciated lol

There are once again *** denoting the really good stuff.

Back to it. As fucking exhilarating as that night had been going in my hotel room, it didn’t really pan out. Last we left off, Emy and I we naked spooning, with all the intentions of getting it in.

Kate, on my other side was backing her ass up directly into mine. Ass-to-ass is a weirdly hot sensation. With my penis pushing hard up against Emy’s little butt, and Kate’s gigantic one seemingly encouraging my thrusts, I was all kinds of aroused. And Emy could feel it.

She placed on of my hands on her small boob and helped me massage it. Both our breathing got louder. Then she reach back around, grabbing the back of my neck and pulled me close. I softly kissed hers. For all the ridiculous, lustful, debauchery that got us there, it was incredibly passionate and sweet. So what we were drunk and she was pissed at me? I had dreamed of touching her like this for the better part of a decade. And for a few minutes, it felt like she had too. Read more »

My Masseuse asked me to spank her and be my Sub [FM]

I know what you are thinking, this is not a story from one of those “massage parlors”, although, I have a couple of good stories about those, too;) No, this was something organic that happened with an actual massage therapist I had been using for back pain. Read on… This might be a long set up, so skip to the ***** marker below if you just want to read the juicy bits.

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A few years back I started going to a legit spa in my manhattan neighborhood for lower back spasms. I had a couple different therapists work on my back and then I met A. She was my 3rd therapist at this spa and after meeting her I requested only her, and eventually she started making office/house calls.

A was petite but strong, I remember being impressed at how good her technique was for such a small woman. She was about 5′ 2″ or so and maybe 100 lbs or so. Anyway, she was and probably is still, a very good massage therapist. I saw her professionally about once a week for 6 months and then non professionally about once a week for another 4 or 5 months. I wish it had lasted longer but I love the memories of what we had. Read more »

I [M] used to cruise for hookers [FF] on Harry Hines in Dallas

In the late 1990s, Dallas’ Harry Hines Blvd in Dallas was infamous for the hookers who would drive cars and motion to you at stop lights, holding their hands in a circle and bouncing it back and forth to their mouth like it was wrapped around a cock. This would start at around 10 PM and last into the wee hours. You would nod, follow them to one of the many parking areas in that sea of warehouses nearby, come to terms and they’d climb in your car and suck you off. The going rate was $40 and they alway used a condom. My first was a short redhead and the only one I also fucked as she leaned against her parked car. I paid her $80. The next was a hot blonde in a van. Another was wearing a Capt American outfit and sucked me while showing a new girl how it was done. One squatted and urinated right there on the pavement in front me after she sucked me. I guess she just needed to go. These hookers would also take you to X-rated theaters and adult book stores so you could fuck them in a private booth but I never did that. I know you can still find hookers there but they don’t drive like they used to and are harder to find. But I don’t do this any more. I admit I still sometimes like to cruise whore strolls because it makes me horny and I then go home or back to my hotel and jerk off.

Inexperienced guy gives a girl an orgasm for the first time! [FM]

My first time giving a girl an orgasm.

This story took place a couple years ago but I’ve never shared it with anyone, it was a dark winters night Me 22 and my girlfriend also 22 were laying on the bed under the covers with some clothes still left on watching Netflix, as you do just cuddling, maybe some light flirting touching each other up, suddenly I felt her arm run down the side of my body onto my crotch and she gave it a small squeeze through my boxers, I looked over, she laughed before letting go, couple minutes later me being me tried to get her back, but I misjudged slightly my intention was to quickly slip my hand under her pyjamas and rest it on her panties but what I actually done was go full on under her panties and touched her pussy she got slightly startled but we both laughed and I got embarrassed and apologised, not really paying attention to the show anymore she leant over and whispered in my ear and I’ll never forget this “please fuck me!” And when a girl says that to you, you’d be stupid to say no, bare in mind I hadn’t had sex a lot due to past experiences and some mental health issues but that’s a story for another day anyway, I wasn’t as nervous as the first time of course but still I wanted to show her a good time and up until this point, I really thought I hadn’t with my performances I really struggled to last long and I’d often bring myself down because of it. Read more »

My insatiable high school bf part 2 [MF]

After writing about it the other night, I decided to do another installment about my high school bf and I (MF both 18 at the time). He was horny and adventurous enough that I have plenty of material from our time together. It helps that I was so new to sex (and totally new to good sex) at the time that those memories really stick out in my head.

Even though he had never had sex before me, he was a very horny teen who watched a ton of porn. Where this can often be a not-so-great thing, in his case it really increased his stamina from what it typically would be for a virgin, and it made him curious and open-minded about a lot of different things. There were always new sexy things he wanted me to try, and he was an animal in the sack from the word go. Read more »

Part III (final) – Watching TV in the basement with my friend when we’re interrupted by the house slut – [FFM]

[The final part of my co-op basement threesome story –

Part I: [https://www.reddit.com/r/gonewildstories/comments/iiiapc/me_f_and_a_friend_are_watching_tv_in_the_basement/](https://www.reddit.com/r/gonewildstories/comments/iiiapc/me_f_and_a_friend_are_watching_tv_in_the_basement/)

Part II: [https://www.reddit.com/r/gonewildstories/comments/ij41b7/part_ii_watching_tv_in_the_basement_with_my/](https://www.reddit.com/r/gonewildstories/comments/ij41b7/part_ii_watching_tv_in_the_basement_with_my/) ]

“Now,” I whispered into Dan’s shoulder. “Fuck me now.”

I felt his biceps tense as his hand moved towards his cock. I couldn’t tell if he had taken off the condom yet, but it seems he hadn’t because his next words contained the slightest hint of trepidation. “Really?”

“Dan, I’m on the pill. I want your cock, not your kids.” That made him smile. “Okay then,” he growled. His arm was rhythmically tensing in a way that made me certain he stroking himself. “Ask me again.”

I pulled him down on top of me so that I could whisper into his ear. “I want to feel your cock inside me. I want you to fuck me full of cum.”

His body tensed on top of me and a low moan seemed to escape him almost involuntarily. When I looked into his face, mere inches from mine, there was no trace of caution there. He was staring into my eyes with a raw intensity that sent shockwaves down my body from my nipples to my now exposed pussy. He groped at my bare chest again, pinching my erect nipples and squeezing my breasts with his free hand. Read more »