[FM] Halloween Night and my first anal experience!

It was my Junior year of High School and I was not a little virgin anymore, at least not in the biblical sense. I had a taste of sex, and I knew I wanted more. So I did what any rational girl would do, I found myself a yummy boy toy to play with. I have always had a thing for unattainable men. All the girls lusted for him, and I made him mine. He knew the deal and was kinky enough to fulfill my very dirty desires. Nick was a 6’ foot Senior, Sicilian, dark and handsome, and on the hockey team. He drove a sexy blue Mustang that purred just like my pussy did for him. As a quick reminder, I am 5’0, very petite, have perky 32C tits, and a very tight ass.

The Principal’s Wench [M40/F18] [nc] to [con] [Mdom/Fsub]

It was the summer before my Senior year of high school and to my surprise our ancient dowdy principal had been replaced by a handsome newcomer to our small town. Not only was he tall, but he had a ruggish handsomeness with a muscular ease to his movement. I’ve always had a thing for older men, but something about the confidence he exuded made me want him even more.

Our town has a small basketball league that many of the local men participate in, my stepfather included. It was here that I first met Mr. O’Connor and sized him up. You can tell a lot about a man by the way he plays basketball. Is he confident or shy? Does he know how to handle a ball, or is he a team player? Mr. O’Connor definitely knew his way around a court. I suspected by the bulge in his shorts, he could handle my plays just fine.

High School Crush justified [MF]

Sometimes there are crushes that have a profound effect on you for the rest of your life. Now in most cases sometimes we end having a bunch of questions unanswered leaving you to wonder and fantasize.
One day, I’m sitting in a bar not too far from where I was living at the time. I was watching the Yankees game and enjoying the beautiful weather we were getting.
The game went to commercial and I make my way outside to smoke a clip of a joint that I had stashed.
As I’m smoking, I look up and see familiar eyes.
Jay was making her way into the same bar and embraced me immediately. Her energy was genuine and I was happy to see her.
We made our way to where I was sitting and we caught up on everything since high school.
She looked phenomenal, she still had some of the best legs I had seen in my life. I had countless fantasies about pinning those same legs down as I stuffed myself deep as I could.
Never the less, she didn’t need to know. We keep talking and one drink turned into several as the time flew. I looked up and it was 1230.
I was having such a good time I invited her back to my place as I didn’t wanna have to worry about closing and incase I got blasted I could just go to sleep.
We get to my apartment and immediately get back to drinking as she was trying to convince me that house music was sexy.
As we go back and forth I managed to grab her and pull her close. Somehow I ended up sucking on her lips and gripping her ass.
Passion, frustration and liquor don’t mix.

Student Seduction [Mf] [Teacher/Student] [Age Gap] [Creampie]

In a place full of scrawny, pimple-faced teenagers, Amber Lopez stood out like a sore thumb.

Like her classmates, she was just eighteen. Whilst the youth in her eyes was undeniable, so was the fact that she had a body that was all woman.

We first met outside my office on a scorching Friday afternoon.

I was immediately caught by the sunlight that reflected off her honey-brown eyes as she turned and faced me. She brushed her wavy strands of dirty-blonde hair aside, revealing the rosy cheeks on her impossibly smooth, caramel skin.

She wore a white shirt that was connected by a singular button in the middle, leaving her large tits to peak out from the seams and her ridiculously tight body on display. Her little plaid skirt barely covered the thick thighs that sat on top of her long, luscious legs. Every inch of her was flawless.

I had never wanted to kiss someone more than when I watched her soft, pink lips form a devious grin. When I looked back in her eyes I could just make out the devilish hint that hid behind their feigned innocence.

Hooking up with the hot punk high school girl from the grocery store , Part 2 (M22/F18) (Age gap) (slow build) (oral)

I woke up in the morning with Liz shaking me. She was holding herself up on one arm and looking down at me with her beautiful face.

“Sam, are you awake? Wake up.”

I gave a very groggy, “I guess I am awake now…”

“I’m hungry.”

“What time is it?”

“Like 9am.”

“Let’s go back to sleep. We went to bed so late.”

“No, I’m starving. Come on”, she starting shaking me violently even though my eyes were closed and I was pretending to be asleep. “I know you’re not asleep…giggle.” She climbed out of bed and stripped off my big tshirt she was borrowing, so she was standing there in just a tiny pair of black panties, as she reached down to pick up her bra. My eyes opened wide and she said, “Oh, I see, now your eyes are open,” trying to cover her tits a little bit.

“You gave me a good reason to open them.” She had a thin body, pale skin, nice firm little tits that really were proportional to her body, and a small, but nicely shaped ass.

Fucking My College Best Friend [M19/F18] [BigTits]

I didn’t lose my virginity until my freshman year of college. I obviously felt very subconscious about the whole situation, understandably. All anyone talks about in high school and college is who is fucking who, and I hadn’t fucked anyone, so I was anxious about it.

It wasn’t for lack of chances. I’m a tall, athletic guy, not overly ripped or anything but toned and relatively well-hung (not that it was public knowledge). But overall, there wasn’t a reason why I was still a virgin, other than just not taking advantage of opportunities I had when I was younger.

Shortly after I arrived at school, I became good friends with a buddy of mine who had attended high school at a rival school close by but was a couple years older than me. I had played against him in sports and knew who he was, but once we got to college we realized we got along pretty well and ended up renting a house along with a couple other buddies to get out of the dorms. A few months later, I finally started hanging out with his sister who was my age.

Cuddles and Sex with My Stepsister Part 1

The sound of lightning snapped outside of my window. It was raining hard outside and had been all day. It was now 10 pm and I was laying in my bed with the lights off and watching television. A horror movie was on as it felt like the perfect movie for a rainy night. It was a B-movie featuring a monster that seemed to target only high school teenagers, especially girls. Many of the girls were half-naked or completely nude when the monster attacked. It was a silly movie but entertaining.

There was a knock at my door. “Hey, can I come in?” My stepsister Darlene said.

“Sure.”

Darlene opened the door and stepped into my room. My stepsister was wearing very short shorts and a t-shirt. Her curly blond hair fell to her shoulders and strands of it hung in front of her face. She closed the door behind her and walked over to my bed.

“What are you watching?” Darlene asked me as she looked at the television. The monster was inside a girl’s house and was silently climbing the stairs. There was a shot of the girl in the shower. The camera zoomed in on her tits.

[MF] She (F18) wanted to give me (M18) the college experience

I’d had the biggest crush on Emily for a couple years now. The idea that an “older” woman would even give me the time of day, much less show any interest in me, was so captivating I found her near impossible to resist. In truth, she was only about 3.5 months older, but that put her a year ahead of me and when you’re in high school, it seems to make a difference.

Emily and I rarely had classes together over the years. I never had the courage to make a move on (aka talk to) her until we were assigned as lab partners my junior year of high school. Our conversations went from minimal to light conversation to flirting fairly quickly, with her tousling my hair every chance she could get (“it’s always so soft,” she’d marvel). I’d stammer through a response, enjoying the physical contact but still fairly insecure. To add to the complexion, she was dating a kid on my basketball team who I wouldn’t consider a friend, but when you’re in the moment, chemistry on your varsity team is important and I didn’t want to jeopardize that. All that said, it didn’t stop us from texting fairly often. One night towards the end of the school year, she texted me late.

Caught my son jerking off into my panties, and then…

A few years back, I started to find several pairs of my panties in my son’s hamper when I was going to do laundry. They were obviously used and very messy and I honestly didn’t know how to react.

This was before we were intimate with each other the way we are now, if you’re at all familiar with my post history.

Anyway.

In the end I did nothing and hoped that he wouldn’t do it again, that it was just sort of a one-time thing, something he did out of curiosity and that I wouldn’t need to talk to his father about it.

His father was a very abusive man who I have since left, but I was heavily under his control back in those days, which meant I always reported everything that went on in our house back to him.

Unfortunately, that was a foolish hope and of course my panties kept popping up in his hamper, all sticky and wet. And the longer I didn’t say anything to him or my ex-husband about it, the harder it became to say anything at all.

I was an adorable redhead’s (26F) first after her divorce [MF]

A few years ago I met with a gorgeous redhead from whisper. I had seen a post of hers when I was on the east coast for business, we started chatting and flirting, hit it off, and decided to meet for a date at the beach boardwalk. Turned out she was very recently divorced at 26, and I was her first “real” date ever, since she started seeing her ex when they were sophomores in high school. They had never really been on a proper date before, which meant I ended up being her first date she’d ever been on.

When I saw her walking toward me in a cute little red dress, she was actually cuter than the pictures she had sent me, which is rarely the case. She was clearly nervous, but a good conversationalist and obviously also quite smart, which I appreciated. We got some sort of board walk snack and sat on a bench and talked, with the conversation quickly moving to BDSM since she hadn’t been able to do any of that with her ex husband and she was curious about it. Between the conversation and how good she looked, I started to get pretty hard under my pants. I was wearing jeans and evidently my cock was pressing hard against the fabric along of the upper part of my pant leg, because she kept glancing down and I could tell she was getting a little flustered. I noticed and asked if she wanted to go find somewhere to park that was more secluded. She asked “and what?” sort of teasingly, and I just responded “I’m sure we’ll figure something out.”