A [F]ormer GFs sister tried to force [M]e to “put a baby in her”

So I’m a pig. I was known for a long time as the guy who would fuck your girl. Or if I was messing with a girl I would try to fuck their friends or family members.
I was dating this girl like 15 years ago. I say dating because she took a liking to me and I needed a place to stay. There wasn’t anything wrong with Melanie persay, I just wasn’t at a place in my life where I wanted to be exclusive with anyone. But she wouldn’t take no for an answer. Thinking back on it I was a huge asshole, she paid for everything and kept me fed and clothed and would stop by the costume shop every week on the way home from work to grab an outfit to roleplay with me. She was short brown hair and matching eyes. Petite build and had her shit together.

[FM] Christmas tree

Let me start with I had no idea it was a date lol Everyone I had spoke with about going to the movies with my “buddy” told me so. I was extremely nervous it had been soooooo long since I’d been on anything close to a date. This wasn’t just any guy either, we met at my old job and hit it off immediately. He’s funny, charming and intelligent the triple threat as I would jokingly say about and to him. I asked a coworker to style my hair for me, went home right after took a shower and did my makeup. I must’ve gone through at least 4 different outfits before I found one that was comfortable and cute, I even sprayed a dash of perfume hehe. He comes over to pick me up in his awesome car, I could hear him from a block away. He gets out and opens the door for me (big points), we hug and omg he smelled incredible almost intoxicatingly so, he had styled his hair and wore a nice outfit, I knew then omg it’s a date!! We headed over to the theater, it was pretty packed that night since it was inside of a mall, we sat at the top row in the center. Half way through the movie he leans over and put his around around me, I snuggled in closer. My heart was pounding out of my chest at this point, my mind whirling, what’s going to happen next? We both look over at eachother and the moment just felt right we both lean in for a passionate/lustful kiss, our first. We proceed to makeout through pretty much the rest of the movie with tons of heavy petting. When the movie ended he extended his hand out to help me up and pulled me in for honestly to date the most precious kiss I have ever received. I thought I was dreaming for a second. He drove us back to my place which has a decent sized parking lot for guests, we couldn’t find any close spots but that was okay. We ended up towards the back of the lot in front of a condo with a medium sized Christmas tree in the window. It was a chilly November evening and the fog was rolling in so the lights from the tree looked magical as they twinkled on and off. Once we had parked he put on some chill step as background music and we started making out again. I recall the windows fogging up in the car from our heavy breathing, so we opened the sunroof slightly. It had been years since I felt this kind of fiery passion. He was grabbing my boobs and playing with them as we made out, he even started sucking on my neck mmm. His hand traced down my body from my boobs to my pants he began rubbing my pussy above the clothes. I wanted him bad, I needed his fingers inside of me, I was squirming so much. So I unbuttoned the top button of my pants and he put his hand in, moved my panties aside to stick a finger in my wet slit, he felt amazing. In and out his technique was perfect I felt like I could cum quickly from it but I wanted to have my fun with him. He had nice jeans on, I could see his rock hard cock through them, I had to see it in person, i wanted him to feel as good as I was. I unzipped his pants and pulled out his cock and started stroking him, I was so excited and turned on (it had been forever and years of neglect from the ex) I was pulling and tugging a tad too much on his cock I felt like I might rip it off. He felt amazing in my hand, I wanted a taste so badly but was hesitant, was it too soon?? We had been kind of messing around for a bit but mostly through sexting, this was the first time we got to play in person. The strokes got tighter and faster, and he was two fingers deep inside of my dripping pussy. He came all over my hand, his hit cum felt amazing. I moaned loudly as I came at the same time as he. We cleaned and sat there for a while to catch our breathe, I hadn’t had so much fun in a very long time. We talked for a while after, it was getting pretty late and he needed to head home. So he offered to drop me off at the front and waited until I got inside to head out. I quickly ran to my room to watch him drive off, such a cool car and an amazing man, I sighed to myself thinking, “what a night.”

I (M24) just had sex with a trans woman for the first time ! (she fucked me) [MT]

I’m a bisexual guy. But I’ve never had sex with a trans woman before, although I was always curious. Today I reached out to this trans girl on Grindr I’ve messaged before and she told me to come to her place. I decided to finally go. In case you want to know, I’m pale white, 178cm (5’11”) tall, skinny, long black hair and a cute young face, with some light beard.

She opened the door for me and she was already topless. She had a nice pair of tits that looked real. She was pretty, brown skin, long black straight hair, had some tattoos. Similar to a cis woman and all shaved.

She put on some music and took me straight to her room. She was very straight to the point, just how I like it. She took her shorts off and I saw her dick, that looked kind of small at first. She didn’t have any tan lines. She quickly got hard and her dick grew to about 15cm (6 inches). We laid on the bed and she told me to suck on it. And that’s what I did.

I [M] fucked a milf [F] inside her clothing shop

There is a small clothing shop, a couple of blocks away from my house. I go there preety often. The shop’s owner is a smokin’ 37 year old milf with big tits and a fat ass. We already knew each other because I visit the shop often. She usually dresses really young for her age. This time she wore a pair of see-through leggings and a red thong which was very visible. I looked around for a couple of minutes when she approaches me:

– Hey there, how you doing, can I help you?
– Yeah I’m good, I’m looking for these exact same pants but a smaller size if you have.
– Sure, let me check.

She bends over to look for another pair. Her ass was right in front of me. The thing and the ass crack was clearly visible. She accidentally rubbed her ass against my leg.

– I found a pair. You should go and try it
– Great. Thanks!

After I tried on the pants:

– So, are they good.
– I’m afraid they are a little tight on me. Don’t you have another pair?
– I’m afraid I dont.

[MF] coworker success story

I posted in another thread about not knowing if my coworker was into me after asking me for lunch. I wasn’t sure as she left the company and told me right before she left.

Boy… was I surprised.

We went for lunch like she asked and after about 1.5 hours, she asked if I would like to come over for coffee. I happily obliged as I still wasn’t sure if she was into me or not. Our conversation over lunch was mostly about work and what we remember doing together when we did work together those seldom times.

Let’s call her V.

V opened the door and welcomed me in. Her cat came to say hi and I went to pet her. Then she asked a question that kinda gave things away and I gave me the hint that she was somewhat into me. She asked “are you always good with cats? I hope you can handle mine”

Sitting at my desk [FM]

Sitting at my desk thinking about last night. How hard your cock was. How it felt trying to fit it down my throat. The struggle and gag it gave me, how wet it made me, the tears it gave me.

I can’t stop thinking about the way your hard cock felt when my pussy lips slid down it, the feeling as I inserted it. Sliding up and down, grinding back and forth.

The way you flipped me to my back and started to slam into me. The closeness, the feel of your breath against my neck. The long hard thrusts.

The way you flipped me again, raised my hips and entered me again with that hard cock. Leaning over me telling me how much you wanted my ass. Pounding into me as I rubbed my clit, I cum, my pussy gripping and pulsating around your hard cock.

You turned me to my side holding my left leg up straight. I can’t stop thinking about the deep thrust. The way you looked down at me. I reached around and inserted my fingers into my pussy with your cock feeling you slide in and out. Watching your face, hearing you moan, feeling my pussy pulsate as I cum again.

[M]y first threesome with my adorable theater geek girl[f]riend and her best [f]riend

[•Story 1](https://www.reddit.com/r/gonewildstories/comments/ctbqf8/winning_over_the_adorable_freshman_theater_girl_mf)

[•Story 2](https://www.reddit.com/r/gonewildstories/comments/cwwcvj/making_my_adorable_freshman_theater_geek_gf)

[•Story 3](https://www.reddit.com/r/gonewildstories/comments/czprap/taking_the_anal_virginity_of_my_adorable_freshman)

[•Story 4](https://www.reddit.com/r/gonewildstories/comments/d3gibq/my_adorable_freshman_theater_geek_girlfriends)

[•Story 5](https://www.reddit.com/r/gonewildstories/comments/dt341q/denying_orgasm_to_my_adorable_freshman_theater)

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This one starts off rather recently than the stories before, a little over two months ago on the first friday night of the school year…

“FUCK *gasp* FUCK *gasp* FUUUUCKKKK!” Rocky belts out as I’m fucking her hard from behind. “imgonnacum imgonnacum IMGONNACUM!!!”

“You cumming on daddy’s cock?” I grunt out to her.

“YEEeEsSss DAdDdDdyyy” Rocky howls back.

I take my index and middle finger and insert them into her pretty little asshole causing her to lose her mind. She mumbles, grumbles, and whimpers as she slowly came on my cock. I was sent over the edge by this and with my final blows I cum inside her pussy filling her up real good. I pull my cock out and observe the [creampie](https://youtu.be/KSXJfqkT36M) I made while giving her ass some spanks. I lay beside Rocky and engulf her in my arms and kissing her all over. We lay there snuggling post-sex for a few minutes before Rocky gets up to clean herself off as I get up to change into my PJs as we fall asleep together shortly after.

[MM] Got fucked by a friend of my Boyfriend

My boyfriend Ali is friends with a lot of guys that he’s met/hooked up with in the past prior to us dating. Every so often I get to meet one of them when they have some party or something. According to my boyfriend, one of his friends who’d I’d met at a movie night at his house (Lets call him Josh) commented on how nice my ass was to my boyfriend. This led to them talking about me some more and my boyfriend revealing some details about our fuck sessions, as well as showing Josh some nudes.

According to him they both got pretty turned on and ended up jerking off next to each other (No touching was involved). My boyfriend and I had never discussed it, and initially I wasn’t okay about him having done that (Even though I got rock hard and imagining it turned me on).

Well it finally happened (again) [MM]

Less than 20 minutes ago I had a cock in my mouth. Now I consider myself straight, and before you go telling me I’m not, I’ve only ever dated women, and very good looking women at that. But lately I’ve been striking out left and right, and too busy to try to set up any long term relationship prospects, and I haven’t had any action in months.

The last girl I “dated” (if you can even call it that) was a 10. There’s no other way to put it. She was WAY out of my league, and frankly psychotic, so I knew it wouldn’t last, but I relished the times I got to explore her flawless body. I wish that was still going on, but alas. Anyway, I haven’t gotten so much as a second look from a female since then, which is possibly the most frustrating thing of all time, so as you can imagine my pent up sexual energy has been mounting daily.