Category: gonewildstories

Mom’s best friend [51F] (from my childhood neighborhood) and me 26[M]

I honestly don’t know where to begin… this one is one of my top sexual moments for a variety of reasons.

TLDR; I lived up my childhood fantasies of my old milf neighbor (currently my mothers best friend) and I think my Mom secretly knows/tries to deny it. What should I do?

I moved into a new neighborhood/town when I was 10 years old. While I lived there, I became best friends with these 2 boys across the street (who were around the same age as me) and we would hangout multiple times a week. I essentially went thru puberty during that time and I had the hots for their MILF momma. She was 50/50 black and latin with an absolutely thick ass. She worked out all the time, was a masseuse while being a stay home mom… she was a milf and it was widely known.
Clearly I was too young to approach her then… lol, I was a minor if you think about it (although I felt older sexually because I was just horny all the time). Read more »

[MF] My Wife Took Boudoir Pictures With her Friends in the Room and Showed me them while Fucking me

I (31M) will start off by telling you what my (33F) wife looks like so you can visualize her. She has 34D boobs, is rather short, has a nice curvy ass and nicely toned legs. She is definitely the dream girl for you if you love big boobs. She won’t let me post a picture of her so this is the best I can do. Don’t be afraid to tell her how hot she is in the comments. That may incentivize her to allow me to post a bikini pic or something.
She is not one to want to send me nude or sexual pictures but she wanted me to have something to masturbate to when we could not have sex when I am horny. So she spent a few hours getting boudoir pictures of her taken and her idea was to give them to me. I did not know she was doing this when she did it, which made this even hotter for me. She told me she was going to see a friend for a few hours.
The pictures were amazingly hot! She got there, had a few drinks, and stripped down to her lingerie she was wearing. It is mostly see through with just a small bra to cover her boobs and a very skimpy thong. She clearly was going for really sexy pictures. She took a bunch of casual ones sitting, laying down on her stomach showing her ass in a thong, laying on her back with her boobs popping out, a few bent over as well from the front showing her boobs hanging down in the lingerie. She told me at this point she had gained her confidence and was even a little turned on herself.
The next part surprised me. She asked if she could take her top off and the photographer told her to do whatever was comfortable for her. So she gets totally topless and follows the photographers instructions on how to pose. She holds her boobs in her hands covering her nipples, she does a few of her laying on her stomach but with her head arched up allowing her boobs to be fully exposed just barely touching the bed, and she does a few of her laying on her side showing off her boobs and body. She never takes her thong off BUT she did put her hand in her panties for a few pictures which was beyond hot. She knows I love porn where the girl masturbates but with her hand in her panties so she did that one just for me.
That is where the shoot ended. I learn all of this one day when we were having sex. She pulls out a 20 page booklet of photos and hands them to me. I open them and see my wife in lingerie and immediately become more turned on than I have ever been. I pound into her as I flip through every page. She ordered them from least sexual all the way to her topless with her hand in her panties. I am literally moaning and sweating because I am fucking her so hard. She loves being fucked hard and seeing me so turned on by her pictures got her really wet, too.
To make me cum, she told me one secret about this whole thing. She had gotten these pictures taken with her three best friends in the room with her for support! So they all saw my wife topless and with her hand in her panties. I couldn’t hold back and immediately came inside of her. What an amazing idea she had. She did it for me but said she also likes to look at them and see how sexy she is. I highly recommend these to any couple as long as you are comfortable with the whole idea. Thanks for reading!

[FM][D/S] Her kids weren’t the one calling me daddy

– I deleted some of my writings a while ago, just reposting them

So it all starts with tinder, I matched with this cute girl, who’s profile hinted at having gigantic tits. But I didn’t know this, I only saw the start of her cleavage in her pics. Along with her cute face, I remember thinking, this is a girl I could corrupt. And boy did I.

We spent about an hour talking before I got her number, and to this day I still remember her final message on tinder before we switched to texts

“I do love a sticky surprise”

And I knew the roller-coaster had started.

There’s a fine line between being confident and getting cocky where you put them off. I swear to god I rode that line as hard as I could and made it my bitch. We were both horny messes, swapping pictures, little teasy clips, but nothing too intense yet. Trust is essential.

Then comes the time of arranging our meet, which for me had to be As. Soon. As. Possible. It’d been a long time since I’d been this worked up and I swear to god I was going to get a rash from how hard she had my cock rubbing my jeans throughout the days of us talking. Read more »

I [m] experienced the best night of sex from her [f] ever

We’ve been drinking all night, relaxing and catching up. Enjoying each other’s company and sharing laughs. We’ve been flirty, sitting with my arm around you and your hand on my leg. We’re in the middle of watching something when you suddenly get up, get on your knees, and start fumbling with my belt and zipper. You’re in such a hurry that you don’t even pull my pants off, you just whip out my now hardening dick and pop it straight into your mouth. I moan in surprise and you use your tongue all over the head as I quickly get rock hard for you. You help my pull my pants and boxers down without my dick ever leaving your mouth. You take a second to tell me to tap your shoulder when I’m close to cumming, then get right back to work.

Now you really start to work my cock, letting your spit drip down the shaft so you can jerk it while you play with the head. My breathing picks up as I hear you slobbering and bobbing on my cock. You occasionally look up at me and make eye contact as your tongue flicks and circles the head which drives me crazy. Read more »

A hot older man got my [F] number.

Was minding my business the other day lounging at a bar, when a tall, dark, and handsome older man spotted me as I was walking past where he was seated. He took his sun glasses off, smiled at me and started speaking. I said hello back to him and it ended with him standing up from his seat to chat and flirt with me, and him getting my number.

I know he was looking at my body. Complimented my legs, and offered to buy me a drink. I turned it down because I was with friends but I told him I might take him up on his offer to go to dinner.

I want him to be my sugar daddy. I know he was thinking about fucking me and what I look like naked while I was wearing my skimpy bikini. My boobs looked so good that day too. He is easily 20 years older than me (I’m 25).

He could give me what I want, and in turn he’d have access to all of my holes, which I’m sure he wants anyways. Read more »

[F]18 Walked in on my neighbor masturbating, cant stop thinking of it.

My next door neighbor and i are really close – you could even say we’re best friends.

Well, at least on his part… he has a girlfriend he has been with for almost 8 months, which is quite long because he’s 18 going on 19 and she’ll be 19 in January. I don’t see why he likes her so much, she’s really vain and clings to him like glue. A couple weeks ago I went to his house to see him and heard this groaning coming from his bedroom, so I peaked round the door and saw him masturbating on his bed!!! I was so shocked I just ran home. But I called up later to apologize and we had a giggle about it. He’s so amazing :)

Anyway, ever since then I’ve been looking at him in a really new way… all I can think about is us having sex! He has suddenly become really really sexy to me, it takes all my strength not to rip off his shirt and attack him! And I’ve been having sex dreams about him too. He is just so down to earth, and funny, and gentle – I actually think I’ve fallen for him! Read more »

Turning a virgin into a sex-fiend [FM]

There I am, swiping on tinder aimlessly when I match with this cute middle-eastern girl. She looked very innocent and even had a head-covering in some of the photos.

Shortly after we met up at a nearby Cafe, and as the conversation (slowly) turned more risque I learned that she was a virgin. The most she had ever done was give a hand job to her former boyfriend (with whom she also had a bad breakup)

We left the Cafe after a while and I invited her to my place, just to “watch a series on Netflix”. She obliged and we got back to mine and started watching something. I slowly but surely started getting friskier by the minute, and soon we were making out.

I touched her between her legs, and despite being wet she pushed my hand away. I didn’t press it, and instead just started touching her tits and pinching her nipples. She immediately started moaning (sensitive boobs, Jackpot!) Read more »

[MF] The message I sent to my sleeping wife that resulted in her waking me with sex after she read it

(If this seems familiar it is because this is a re-upload of a post I originally made on my main account. I now have a NSFW account so I have deleted the original.)

It’s late, after 1am.
You have not long come back to bed; that’s what woke me. You’ve tossed and turned a bit, and you’re facing me, resting your hand on my bicep. I know you’ve been sleeping poorly recently, so I start stroking your skin because that’s helped to settle you before.

I start with your arm that’s holding me, moving the pads of my fingers lightly across your skin, and you make a pleasant noise; something halfway between a sigh and a moan.
After a short while you roll into your back. I start stroking your other arm, because it’s closer and more accessible. When I run my fingertips over your inner elbow you make the noise again. That noise stirs something in me; I love it, and it makes me want you. But that’s not what I’m trying to do – I just want to help you relax. I stop stroking your arm and move my hand – my fingers – to your stomach; you’ve mentioned before that my gentle touch here has helped you get to sleep. Read more »

Nervous for G[F] to take her first BBC

My GF and I have given each other hall passes and she has been talking to a guy for a while planning it out. She has sexted with him and he is a BBC. At first I was excited to see her take him into her tight little pussy but now that they are about to follow through with it I am having second thoughts. The plan was for us to get side by side hotel rooms so that I could get her all wet and horny before sending her over to him. Then I would get to hear her getting the shit fucked out of her. They also were gonna take some videos to send me while he has his way with her. I thought it would be hot af to watch her suck him off and see how well she handles his BBC but now I’m not sure how I feel about it.

Three years later, I randomly ran into my prom date Jenn, almost had a threesome with her friend Molly, fucked her, and came on her tits [MFF]

From across the apartment complex parking lot I saw an unmistakably familiar figure walking in the yellow streetlights.

“Jenn?” I called out. She recognized me and waved, then walked across the way to me.

“Hey! How the fuck are you?” I asked. She stood in front of me, tall, somewhat gangly, and girl next door cute, brown eyes, shoulder length brown hair, and a distinctive nose. I think objectively speaking she was average looking, but there was just something amazing about her eyes and her smile – reader, you simply can’t explain any of this to someone didn’t feel the same nervous flutters every time she looked at you.

“I’m great, how are you?” she asked in reply, gesturing to my outfit, which happened to be a colorful pink sheet wrapped around my body, flip flops, and a plastic crown of olive branches.

“Oh, um, toga party,” I explained with a goofy grin.

“I can see that,” she laughed. Read more »