Tag: Girlfriend

[M]y childhood [F]riend helped me get over my ex

This one comes from a few years ago when I was nearing the end of my time in college. All through the end of high school and first few years of university, I had the same girlfriend. Ana and I were the super saccharine high-school sweethearts that you normally only see in movies. She was on the swim team, I was on the soccer team, and the two of us maintained genial relationships with almost everyone we interacted with in high school. “Popular” is a loaded term, so I won’t say that that’s what we were, but we were definitely well-liked. People were generally rooting for us to live happily-ever-after and we gave them every indication that we would.

That facade persisted through our first couple years in college. I can’t exactly explain why I fell for Ana so hard in high school, but there was something about her that just felt… intoxicating. Like, I was drawn to her in a way that I couldn’t articulate. It was probably her eyes. As much as I appreciate a well-developed physique, there’s something about *eyes* that enchants me, and Ana had these beautiful blue eyes that transfixed me whenever she looked my way. Read more »

Fucking My Best Friend’s Dad

My family moved from California to Texas four years ago, during the summer before my freshman year. Entering high school was going to be hard enough, but to do it in a completely different town, a completely different state, I wasn’t so sure. Amanda made it easy. I met Amanda the day after we moved in. July, in Texas, is hot; the sun lives here, I swear. The doorbell rang, I opened the door, and there she was. Amanda. Wearing shorter shorts than we wear in Cali, a skimpy little tank top that halfway covered her bikini top. She was 14, same age as me. That afternoon she would become my first friend in my new home.

Freshman year breezed by, thanks to Amanda. We played together, studied together, talked about boys together. Our bodies became more developed, filling out our bikinis a bit more nicely. We were both on the volleyball team, skipping cheerleader tryouts, at least for freshman year. Sophomore year was more of the same. Amanda talked me into trying out for cheerleader. We both made it! More studying together and talking about boys, and practicing our cheers. My first kiss, my first real kiss, was with her. It wasn’t a lesbian type kiss or anything. Neither of us had ever kissed a boy, and Amanda had a huge crush on this guy, I don’t remember his name, but he asked her to Spring Fling. She was freaking out. Read more »

When daddy has a bad day [MF] [Freeuse] [NONCON] [DDLG] [spanking] [Degradation] [impact play] [PAINAL]

As I lay on the bed kicking my feet around in my fuzzy thigh-high socks, I hear the door jiggle. Daddy’s home. I sit up and turn the TV down, beaming at him as he walks in. “Hi daddy!”. He doesn’t look up. He just kicks his shoes off and grunts. Uh oh, a bad day. I try to be the best girlfriend I can be, and get up to help him relax. I walk over and kiss his neck asking if everything is alright. “Fucking no good sons of bitches. Do I have writing on my forehead that says fuck me?” I giggle, “No daddy, you definitely don’t.” He sighs. “I’m sorry princess, it’s just been a hard day for daddy”, he says while kissing my forehead. “How was your day?” ” Well I made cookies watched Halloween movies and had a nap, so it was pretty amazing” I giggle. He chuckles and cups my face. I look up at him smiling. I can see his eyes shift and I feel a sharp slap hit my face. Although it’s normal for daddy to take his stress out on me, I wasn’t really expecting it at the moment. Daddy likes to watch me whimper or squirm in pain, and I don’t mind it really, but it always makes me tear up. Read more »

[MF] How it all started with Vivien

Vivien and I were in the same year at university and became friends there. We were both pretty nerdy there. She is quite a genius and was in our school year 2 years younger than me and most, which I found quite impressive besides her great ambition. To the outside world, she seemed rather cold and dismissive, which many thought was arrogant. I judged this more as insecurity and saw an interesting person behind this facade.

So I did my best to break through this protective wall again and again and loved to tease her, with which I could really drive her up the wall. There were many moments when she blushed and stared at me angrily. Still, she seemed to like my attention and played along with my game.

We spent a lot of time together in our study group and got through the first year at university reasonably unscathed. Slowly a good momentum had developed, I had the feeling to understand Vivien very well and my advances to her became more daring without consciously controlling it. We were both in a relationship with someone else, but neither of us was happy with it. We unconsciously became like substitutes for each other and our conversations more intimate. Read more »

She Stripped For My Groomsman [MFM]

This started a long time past, at a friend’s house in High School. It was late at night, we were young, David’s parents were gone and we were very drunk. Everything began with a pin toy. A bunch of pins held in a frame that retained the impression of anything pressed against them. The kind of thing that executives have on their desk to show that they are whimsical, but not too whimsical. They’re trademarked under the name “Pinscreen.”

The toy was on the desk of his father’s office when Anne found it. She became obsessed with it. Hands, Face, ears. She loved making impressions in the cold steel pins. I think they felt new and exciting against her skin. Anne escalated from her own skin to mine and eventually to David. She started with his hands, but moves up to his ears, then his face. He was obviously uncomfortable, not with the attention, but with how to handle the attention. David didn’t have a girlfriend. He’d never had a girlfriend. Having Anne this close, focusing on him, touching him, was leaving him flustered. He kept looking over at me for guidance. I was happy to just watch things unfold. Read more »

A Convenient Affair Ch. 5 Party Favors [M38/F44] [Cheat] [Con] [Affair]

*Sorry for the long wait, I’m going to try and get on a better schedule! As always, any feedback is welcome and appreciated, hope you all enjoy!*

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Nicholas stepped into the house, both arms lined with bags from the store with all the items Tina had requested for the party. He shot her glances as he struggled to open the door a little, watching her sit there and just talk away on the phone with Stacey. As the bags hit the floor, Tina threw a look back at him for him to be quiet since she was on the phone. Nicholas shook his head. *No, no I don’t need any help at all h*e thought. He smiled to himself a little, thinking about all the help he had gotten from Lee just the other day, that innocently seductive image of her still on his mind.

Tina had hung up the phone after a bout of cackling, she got up heading towards him. She was carrying a box.

“Got a fun little package here today,” she said, shaking the box. Nicholas just looked at her, reaching for the box as she handed it to him. Read more »

Change Happens: Chapter One (Part One of Two) 21+ {F36/M38] [Straight Sex] [Busty] [Huge Boobs] [Creampie] [Quick Sex]

Chapter One: The Same Old

I knew what she was thinking. “She is a slut or a prostitute,” was what most people thought about me when they first looked at me. After all, I was used to it, built the way I was and the way I dressed. I was practically asking for it.

I waved at the woman as I passed her by the oranges in the produce section. My heels clicked and clacked on the tile floor, and I smiled at the poor produce clerk as he looked at me. When I passed, I heard the familiar noise of something dropping.

‘Poor guy,’ I thought to myself.

Another woman stared at me with eyes that could bore a hole through metal. Again, I just shrugged it off. I couldn’t help it.

I loved my body. What was the saying? If you got it, flaunt it. Well, I had it in spades. Long dark black hair and an athletically toned body that I took care of every day at the gym and at home.

I ate healthy because I wanted to keep my figure. I hardly drank and never smoked in my life. The payoff was a body I loved, and so did my husband, Jeff. Read more »

My girlfriend’s mom seduced me…again- Part 1 [55f] [18M] [Cougar] [Femdom] [Interrupted] [Deep Throat] [Girlfriend/Mother] [Seduction] [Part 1]

Chapter 1
It had been almost a week since my cock was inside my girlfriend- and her mother. Five days of working at my summer job as usual, talking on the phone with Lexi at night. When her mom Crystal would answer the phone, she was her usual warm self, completely nonchalant- as if she hadn’t gagged on my cock last weekend. Lexi was also completely normal, planning our movie date this weekend without a thought to how our universe had changed- as if seeing her mom’s tits (not to mention seeing Lexi eat her mom’s pussy) hadn’t completely turned everything upside down.

I had thought many times that maybe I hallucinated the whole thing- that would be a far easier explanation for what had happened. I almost convinced myself that was the case, until Lexi ended our phone conversation the other night with “I can’t wait to feel your cock in my ass again this weekend. I hope you’ve been saving your cum for me.” Nope- not a dream. Read more »

26 [MM] I lost a bet to my friend and had to show him my pics/vids of my girlfriend, and ended up blowing him while he viewed them

Last weekend I was hanging out with one of my friends, playing video games and having a few drinks. He was telling me about a girl he had been seeing for awhile and we talked about my girlfriend for a bit. Being very competitive he challenged me to a bet, where if I won a game he’d show me the picture she had sent him the other day if I’d offer the same. I was a bit hesitant but he talked me into it.

I lost a close game and ended up showing him a picture of my girlfriend in lingerie biting her lip seductively. He took a long look and told me I was lucky and how he thought she was attractive. I liked hearing it so I asked more about what he liked and he went on. Excited by it all I challenged him to a rematch offering up the folder where I had all the pictures and videos of her saved. He offered something similar. Read more »

My Landlord Part VI [MF] [Vanilla] [Hand Job]

*I really advice you to read the previous parts first.* [*The parts I-III are over there*](https://www.reddit.com/r/dirty_boy69/comments/wxc08b/my_landlord/?utm_source=share&utm_medium=web2x&context=3)*,* [*parts IV-V are over there*](https://www.reddit.com/r/dirty_boy69/comments/xl044a/my_landlord_ii/?utm_source=share&utm_medium=web2x&context=3)*. Enjoy your read.*

The next morning I woke up with a raging hard dick between my legs. I had a severe case of morning wood. Luckily my landlord’s daughter, well, meanwhile more my girlfriend, was laying next to me. And she was awake too. So I began to kiss her neck.

She immediately knew what I was up too, turned herself around and pulled back the blanked: “Lay down on your back. Just enjoy yourself. Let me do the work.”

Then she gave me a gentle kiss. A gentle kiss that turned into passionate kissing while her hand was sliding up and down my rock hard dick. She knew what spots she had to hit, but she made it all even better a minute later: She wrapped her lips around my glans while she was squeezing my balls.

My cock sliding in and out of her mouth felt awesome. I came closer and closer to an orgasm. Moaning was leaving my mouth. But she stopped before I jumped over. She stopped before my balls emptied themselves down her throat. No, not to keep me blue balled, she wanted to feel my dick inside her. Read more »