Tag: Anal

Afternoon Delight in His Office [M, tF, F] [Anal] [Rough] [D/s themes]

This all started following a submission from a very good gurl who’s a follower of mine:

>I found myself daydreaming the other day. I found a cute little pencil skirt and put it on and I thought how good it would look if I put it on, with my tall black heels and a silky white blouse and visited your office for a ‘meeting’. I thought about being on my knees in this tight little skirt, working my lips up your hard cock all nice and slow. Ruining my lipstick on your hard, glistening cock. Then I found myself wondering what you would do to my little, tight sissy boipussy now that I had gotten your cock all hard…

As your mouth and hands devoured my cock with me leaning back onto the desk… I’d wrap my hand up in your hair, controlling every up and down, forcing your mouth to take more and more of my hard cock into it. I’d lean back and press the intercom button, telling my young, shy assistant to come inside. And there you’d be, on your knees, stroking my cock in your hand, looking back at her wondering what I had planned next. I’d tell her to close the door and come a little closer. Read more »

I helped take her cherry, and I’ve never [M]et her.

This is an absolutely true story.

Wayyyyy back in my AOL days (1990s), I met an 18-year-old virgin online. She was a college freshman who was curious about sex but had virtually no experience. I kept trying to push the conversation in a more sexual direction, but she had (frustrating) limits.

She asked a lot of questions about sex and was quite curious. I kept hoping to ramp it up, but it wasn’t happening.

We’d drift in and out of email contact. Neither of us was into cybersex, and she wouldn’t do phone. She wouldn’t give me her mailing address. I sometimes wondered whether she was real (spoiler: she is).

Eventually it emerged that she wanted a vibrator, but she was afraid to buy one. She wouldn’t go to a store, and she didn’t want a mysterious package showing up at the small college she attended.

The U.S. Post Office has an obscure and ancient service called General Delivery. This is an old-fashioned service where you go to the PO counter and ask whether they have mail for you. It’s addressed like this:

>John Doe
>
>General Delivery
>
>City, State Zip Read more »

[MF] The FWB with the freeuse fantasy

Her profile on POF was very standoffish, one of the types that some people use to troll dudes with. I took the bait and whipped out my fresh banter because I was bored and wanted a challenge. She accepted and as we bantered back and forth she was amused and we traded phone numbers and pictures. Soon after we setup a time for her to be over. It wasn’t as simple as that everyone, but I want to set a quick stage for the events that followed.

She was a big girl, but strong. Imagine Gwendoline Christie but shorter with some D cups, same short hair. She lifted weights, but also lifted food like no one else. She came through my door with her bag of mini bottles and a 2-liter to mix them because this is how my life was at this point, and I accepted a certain amount of crazy and frenzy. She starts hard and we flirt and chat. She had told me she was married and that it was unhappy, but hearing that it had been years of no sexual contact made me feel especially bad for her. So I played my part, made her feel relaxed and at home. Feeling more at ease we would stand and sit closer and closer together. Why was that worded like that? Because she couldn’t stand still and she was anxious. We soon found ourselves within kissing distance. I put my arms around her and slowly went in for the kiss and let her finish the distance. She was a sloppy kisser, lips over mine and her hands started rubbing my crotch. After a minute of making my face wet she started moving towards the bedroom and I followed. Read more »

My first time meeting my sister, the last time ever seeing her… a murder fantasy.

When I first met my sister, I was 22 years old and being introduced to a sibling I never knew existed. My dad had a daughter with another woman while my mother was taking care of me, while I was still just a newborn… my dad was not parent material, so he just up and left us both to have two more kids. But one day, I logged on to Facebook and saw a new message from a beautiful girl with auburn hair and green eyes:

“Hey, this might sound sort of strange, but I discovered you after I did an ancestry search. You’re my brother, our dad had me with my mom around ten months after you were born. I’d like to meet you, would you be available to get together?” Read more »

Losing [M] My Virginity to a [F] Dirty Girl

Retired (early) fellow here, sharing stories about fun and wild escapades. Long story but please stick with me.

I was awkward around girls in high school and had a couple of dates, but I was still a virgin when I graduated. So off I went to a small college that fall, enrolling in a rigorous liberal arts program that required you to live in a dorm your first two years. All of the freshman and sophomore students, as well as a few upperclassmen, lived in a cluster of four dorms and shared the same dining hall. Many of the classes were held in rooms in the dorms, and the social atmosphere was strong. While the dorms were same sex, rules about visiting were not enforced except if campus security caught you, which was a rarity. So as you see, it was a tight-knit environment, and it engendered a lot of hanky-panky. Read more »

[FF] My exs first girl/girl experience

This story involves the same ex I talked about [here](https://www.reddit.com/r/SluttyConfessions/comments/ewv8l9/atm_with_my_ex/?utm_source=share&utm_medium=ios_app&utm_name=iossmf), and a girlfriend of a former friend of mine.

So after the first year of just oral and anal sex, my ex Erin decided she wanted to lose her virginity. Doing that with her fully awakened her inner slut. Suddenly, she was down to try anything. She also got aggressively submissive, if that makes sense. She loved being dominated, tied down, had a huge rape fantasy kink, became an exhibitionist to the point that we fucked in public more than once, and would generally try whatever to get both of us off.

She also would get insanely horny whenever she got drunk.

One night, we decided to go to a friends birthday party. It was your typical college house party until the birthday boy got a little too hammered and then it all dissolved into a shit show. Erin spent most of the night trying to reassure the birthday boy’s girlfriend that everything would be ok, holding her during the worst of that guy’s total fuckboy meltdown, and giving her the occasional kiss. Read more »

Fulfilling a Fantasy [Gay] [MM]

Sex with a man. It’s a fantasy some straight guys have but few act on it. For quite a while I have thought about going through with it. I didn’t really have a fantasy guy picked out, except for one aspect… his cock. My fantasy guy had a big cock. I figured if I was going to go through with the fantasy I would go big or go home. I would talk to guys online and it would get me hot, but as soon as I blew my load that desire to try it out for real slipped away. Heather and I had talked about these fantasies at length; the idea of me hooking up with another guy was as big of a turn-on to her as her being with another woman was for me. Sometimes we would bring ass play into the bedroom and I went as far as buying a strapon for her to wear. Still, nothing happened beyond talking. I had pretty much concluded that it was always going to remain a fantasy, one not to be acted upon. Read more »

My Good Friend [MM]

First time posting as I was looking for a place to discretely share some real-life events that happened between a long time friend and myself, and this looked like a good place for it. I’m not a writer, so I apologize in advance for any grammatical errors or bits that just don’t read like they should. I hope someone reads this and finds some enjoyment from it. Read more »

[MF] my [f]irst time being tied up and fucked in the ass

Apologies in advance for bad formatting, I’m posting on mobile.

Anal always seemed like such a terrifying concept to me. If I’d have known how fucking good it was I would have taken the plunge much sooner.

To set the scene I am a 28 [ f ]small tits, banging ass and tight body and also a closeted freak. And the real hero of this story, let’s call him Lee 34 [ m ] athletic with the body and cock of a god. Read more »

I[F] had sex with my professor[M] in his office [long]

I am a university student, second year. I’m a short brunette and have a healthy weight but was blessed with D cup breasts and a great ass. He is tall, has dark hair and a very fit body. This story happened just a few days ago and I needed to share it.

For weeks, there already had been some tension building up between us. Being the only active student in his class made it easier to have a closer bond with him. He is 9 years older than me and very attractive. He spoke with such passion during class that I couldn’t help but fall for his charm. I pretended having trouble with an assignment to get his phone number and started texting him about it. Soon enough we were talking about other stuff and flirting instead. I asked if I could come by his office to show him a draft of my work and he agreed. I had many unclean thoughts racing through my mind already. All about him using me in the dirtiest ways… Read more »