[F][Masturbation][Anal] Young me discovering anal masturbation

Heyy everyone! <3

This story is about me. I was a younger girl in high school at the time. I was just getting around the age where I was sexually piqued. As my body developed, so did my interests in the sexual sphere of life. I spoke to friends of mine who would describe their sexual experiences. It wasn’t that I was desperate to relate. I was desperate to find out more.

A bit less than a week before this story happens, I began masturbating. This came after many fantasies about both boys and girls, and the sexual acts known to me at the time. Primarily, I was a more submissive role in these fantasies. The boy/girl performing the act would often be pleasuring me for many, many minutes on end. Unfortunately, it took me quite some time to discover that I could enhance this experience via masturbation.

I looked up some wikiHow-style articles on the subject. I watched girls talk about it on YouTube, I read articles and even looked at a couple pictures (insane for me a few years ago). I’ll write about my first vaginal masturbation at a later time. For now, I’d like to start with this story, because it was a whole different level. It was a much different experience.

Three licks [MF]

“I was perpetually hard in biology class,” Connor said. “I guess I just love science.”

My fianceé Danielle returned from the bar carrying two dark brews. She slid into our circular booth and handed me one. “I only heard the end of that anecdote,” she said, smiling at Connor. “It sounds like a good one.”

“Connor and I are trading embarassing stories from middle school,” I interjected. “…For some reason, I’d always get a boner when it was time to get off the school bus.”

The conversation made Isabelle, Danielle’s best friend, start blushing. Connor was her new boyfriend, and I guessed it was their first time talking about sex. “Anyone want to share an appetizer?” she asked, blatantly changing the subject.

Isabelle and Danielle are physically similar. They’re in their mid-20s with fair skin and blue eyes. If there’s a genetic lottery for boobs, they both won the Mega Millions. But their personalities are a world apart. While Danielle is bold and adventurous, Isabelle is softspoken and conservative.

To diffuse the tension, I told Isabelle, “Yeah, let’s check out Happy Hour specials.”

A last-minute hotel meeting [FM]

A couple of weekends ago was my final cosplay convention of the year, and it also meant a weekend away with a friend of mine who I hadn’t gotten to hang out with for quite some time. In theory, I was planning to put any “other” activities on hold for the weekend so I could dedicate myself to catching up with her after so long, but old habits die hard…

In a moment of weakness, I decided to make a post on Craigslist in the run-up to the event, although of all the responses I got not too many caught my eye. I did however make some plans for the second day of the event, only to be let down by a rare event – a guy not simply not showing up, leaving me with time wasted and an itch unsatisfied. This kind of thing happens to everyone I suppose. Too irritated to even stay put in my hotel room and masturbate away my frustration for a while, I simply stomped back to the convention to find my friend again with something of a cloud hanging over me.

Unintended mutual masturbation with my little brothers friend [FM]

I’m Sara, a 26 year old female and I was watching a movie with my little brother John and his best friend Alex who are both 18 while I was home visiting the weekend after thanksgiving. It was about midnight when we started watching the movie. To give you a little bit of an image, we were all three sitting on the couch, I was on the left side of the couch with Alex to my right and my brother was on the far right side. I’m about 5’6″ 120 lbs with long dark brown hair and porcelain pale skin. I had on some comfy black boy-shorts and a loose fitting white t-shirt. Alex is about 5’11” 170 lbs with short styled dirty blond hair with a nice fit body with an olive complexion.
About half way into the movie we all got under one large thin fleece blanket and shortly after my brother and Alex fell asleep. I stretched my legs out over Alex and got comfortable intending to fall asleep myself in the near future. As I laid there, my feet innocently in Alex’s lap a rather sexy scene came on the screen. I thought Alex was asleep but he must have just been sitting there with his eyes closed. As the girl in the movie continued to moan I felt something under my leg, it didn’t take me long to realize it was Alex’s dick. I could feel it easily through his gym shorts, it felt pretty big but then again it was against my calf so it was hard to tell. Suddenly my heart started pounding, I didn’t know what to do! I was kind of excited and nervous at the same time. I felt Alex trying to rearrange himself so his dick wasn’t pressed against my calf and panicked and pretended to be asleep.
We both sat there for close to 45 minutes pretending to be asleep, afraid of the other noticing what the situation here was. The movie had ended a while ago so it was dead quiet. Alex had rearranged himself so that his dick was tucked up in his waist band. I was incredibly wet just from sitting there, I found myself wandering what Alex’s cock must look like. He was a very attractive guy in good shape and his dick felt pretty big! I shifted myself as if I were rolling over in my sleep and slid my ass down closer to him, almost in the fetal position with my face facing the back of the couch causing my feet to angle back towards his cock. When I my toes brushed across the tip of his cock since it was sticking out of his waist band. This had my heart racing and my juices flowing, I continued to pretend to be asleep though. My toes were now just at the base of his cock. After laying there for a few more minutes I started to feel a little movement just above my feet.
I slowly peaked out of my left eye to see Alex sitting there looking at his phone but I could’t see much else. I was almost positive he was touching himself but couldn’t tell for sure. I slowly moved my foot up a little so it was resting against the base of his cock, I could feel his warm balls under my foot. It felt like he was moving when I first moved my foot but now he was completely still. Both of us were being as still as possible, I don’t know if was just me being incredibly horny or not but I felt like I could feel the sexual tension in the air. After maybe 5 minutes I felt him moving again, he was definitely running his fingers over the tip of his dick. I was soaking wet after realizing what was happening, I slowly moved my hand over my panties and they were completely soaked! I’ve been really wet before but never wet enough to completely soak through my panties.
My body was buzzing with excitement! I wasn’t sure if he knew I was awake or not but I was pretty sure he though I was asleep. I know my brother was asleep, he was snoring lightly but consistently on the other side of the couch. Alex set his phone down on his leg to adjust his shorts, which he pulled the waistband of down further, I suspect to reveal more of his dick. On his phone I saw a video playing of a compilation of cumshots on hot young girls. I got to watch maybe 3 or 4 before he picked his phone back up. I couldn’t stop thinking about his cock and wondering what his cum tasted like, God I would have done anything to have a guy cum all over my body right then. I adjusted myself a bit, trying trying to strategically move the blanket so I could see him better. It worked! Now I could clearly see his face and upper body, one of my legs was now outside the blanket holding it down so it didn’t block my view. He pretended to be asleep for a few minutes before I felt him masturbating again, this time I could see that he had his shirt pulled up a bit and I could see his and moving under the blanket. God he was sexy, I could see his lower abs flexing as he leaned forward to bit to see his phone. He looked over at me several times to see if I was awake, I was just barley peaking so he couldn’t tell I was watching him. I guess it took him a while to decide I was actually asleep, he knew my brother was asleep thanks to his snoring and pulled the blanket down a bit. My body was buzzing and my heart pounding as I got my first glimpse of his very nice, thick and very engorged dick. I couldn’t help but start rubbing my clit now, it was incredibly hard to stay quiet and not let him notice. My eyes moved back and forth from his face to his dick, which was now starting to glisten his precum started leaking from it. I watched him touch his finger to the tip stringing precum onto his stomach as he pulled his finger away. I could feel myself getting close as I watched him play with his now precum soaked cock. Right as I came I let out a small moan, it wasn’t very loud but it was definitely noticeable. He stopped immediately and looked at me, I was terrified of him realizing I was awake and wanting him to at the same time. He whispered “Sara are you awake?” I didn’t know whether to answer or not. We both laid there not moving, after what seemed like an eternity he slowly started rubbing the now red throbbing head of his penis and pulling the blanket down more until most of my lower body was revealed and from his lower thighs up, I pretended the blanket moving woke me up a little and moved a little spreading my legs. I saw him staring at my legs and up to my shorts that were obviously wet, I saw the moment he noticed and almost came again just from the look on his face. “Sara?” he whispered. “Can you hear me?” I kind of mumbled “Hmm?” Alex asked “Are you awake? What have you been doing?” I didn’t say anything but spread my legs a little more and slid my ass even closer to him, I was now laying on my back, the blanket was pretty much completely off of me and when I slid toward him it pulled my shorts tight on my pussy which was very VERY engorged. I swear I hear him moan. He started masturbating again and that when I felt his hand lightly touching the inside of my thigh and working its way up my leg. When his hand touched my shorts and he felt how wet they were I heard him whisper “Oh my god!” I sleepily opened my eyes and said “Alex? What are you doing?” He started to trip over his words trying to explain. “You can lay down behind me if you like, I know you would be more comfortable” I said. He hesitated for a moment before sliding down behind me, I sat up so he could slide his arm under me and get comfortable. “Were you awake this whole time?” he whispered. I didn’t say anything but I let out a little moan and kind of snuggled into him. I felt him start getting hard again, his dick was still tucked into his waist band. My shirt had moved up my back as he laid down behind me leaving it exposed, I could feel his warm cock against the small of my back. I didn’t move or say anything, I was starting to like the fact that he might think I was asleep. I could feel him ever so lightly moving back and forth, it wasn’t long until I could feel is precum on my back which was incredibly hot. “Sara? You sure you’re not awake?” He asked again. Do you mind me do this?” I just kinda adjusted myself pressing against his cock a little. I could feel it pulsing now. He slid his hips down dragging the tip of his dick down my back, I could feel his precum as he did it. He pulled my shorts down a little revealing my ass. “This okay?” he asked. Again I didn’t say anything and just ever so lightly pushed my ass against him. I pulled my shorts down a little more so that my whole ass was out, I felt him pull his shorts down letting his cock out and he pressed it between my ass cheeks and his stomach. It felt huge! I was so turned on!
He started slowly moving his hips, sliding his cock against my ass. It was so hard not to make any noise but I loved him not knowing I was for sure awake. I could feel precum running down my back, it was the sexiest thing I’ve ever felt. He slid down a little farther and slid his cock between my legs, I had to adjust my legs a little so he most likely knew I was awake. I peaked without opening my eyes fully to see a very hard and swollen cock sticking out and I could visibly see precum dripping from the tip and I could feel it running back down his shaft onto my pussy and legs. I tightened my thick around his dick. Alex pushed my forward a little so that the tip of his dick was sliding back and forth over my clit. I couldn’t help it and let out a moan. I could feel him getting closer so I kept moaning really softly. Each time he pressed forward I could see the head of his dick and precum was starting to pour out faster and faster. I reached down grabbing the head of his dick, it was absolutely soaked between both of our juices and he grabbed me tight. I could feel Alex tensing up and could feel the cum building up in his cock. He pulled back so that the tip of his dick was pressing against my pussy, I could feel him trying to push it in. I wanted him to more than anything but I’m not on birth control. I squeezed tight and thankfully he had a big dick or as wet as I was it would have just slid on in. I felt his dick start pulsing and he started thrusting harder and harder, I felt hot cum spraying against my pussy and legs, I was amazed to feel him keep cumming. It was so much that it was running down my legs onto my knees. After a few more pulses I could feel his that no more cum was cumming out of his dick and he sat back relaxing his muscles. We stayed like that for another 30 minutes or so as I basked in his cum and replayed the hottest thing that has ever happened to me in my head.

Annie and Jess, high school besties [ff] [anal] [oral] [mast] [fist] [pee] [spit]

Annie and Jess, 18 year old seniors in high school, spent almost every weekend together. They’d order a pizza on Friday, do their nails, talk about boys they liked, give each other mud mask facials, and eventually, change and snuggle up and go to sleep.

But you’d be fooling yourself if you didn’t think there was some sexual tension between them. They’d always linger a little when they hugged. In bed, they’d run their fingers through each other’s hair and breath on their necks as they snuggled.

Neither one was courageous enough to make a move, though, until one night, Jess’ parents went out of town and Annie came over. Annie, horny as all get out, wanted to fool around.

“I wish I had a boyfriend,” she said. “I’m super horny.”

“Oh my god, me too,” Annie said as she went to Jess’ dad’s liquor cabinet and opened it.

“What are you doing?” Jess asked.

“Shhh, it’s okay. I just want to try something.”

Annie pulled out a nearly full bottle of vodka and took a small sip. She handed the bottle to Jess, who also took a sip. They took a few more small sips, giggling, blushing nervously.

Callie Piss Drinker [mf] [mast] [pee]

Callie and Alex were friends who had this insane sexual chemistry. But since they had been friends for so long, neither party pushed the envelope.

They’d talk about every lewd thing on the planet, from how big were his loads to how often she masturbated. If she needed a guy’s opinion on something, Callie would text and ask. He never held back and she never held back and that’s how they were able to become so close.

But the tension was INSANE. They’d often end their chats and run off and masturbate thinking of what it would be like to actually fuck.

One day, during a heavy snow, they went for a walk. She’d just been with a guy the night before and he fingered her asshole without asking. It rubbed her the wrong way. Alex asked for every detail, which she shared and he memorized in order to jerk off later.

Halfway through their walk, Alex grimaced.

“What’s wrong?” She asked.

“I have to pee really bad and I thought we’d be at the bar by now but all this damn snow …”

“Go pee in the woods,” she said.

Snapchat Sex [mf] [mast] [cum]

Jenna and Mark were friends on Facebook, but they never met in person. It all started when he liked a comment she’d left on a shared friend’s post. After a string of liking one another’s mutual comments, he friended her.

One day, Jenna saw Mark online and messaged him, full of tears. “I’m getting a divorce,” she said with a sad face emoji.

They spoke for hours, eventually moving to the phone. She was beautiful, but her voice really sealed the deal. Mark had developed a crush on her.

“We haven’t had sex in two YEARS,” she said.

“Wait,” Mark said. “You have a one year old. How is that possible?”

“He wanted another kid. Thought it’d save the marriage, but we couldn’t stand the sight of each other, so … he took care of himself while I waited and then he finished in … me.”

“That’s the saddest thing I’ve ever heard,” Mark said.

Old Friend Becomes a Play Toy [mf] [oral] [anal] [mast] [piss] [cum] [selfpee]

Jake and Claire had been friends for ages. When he got dumped, he called her in tears. Claire came over with a bottle of wine and they sat and talked and she assured him everything would be okay.

Some months passed and Claire picked up the phone to check on her friend. He was still in a funk, which was to be expected, but Claire knew something had to be done. She had to bust him out of his depression. And she knew the best way to do that.

A few hours later, there was a knock on Jake’s door. Claire had bought him a puppy! Just kidding. It was Claire and she was in a trench coat.

“Hey there,” she said. She pushed him to the side and stepped into the living room.

“What are you doing here?” He asked.

“What am I NOT doing here?” She said.

“Huh?”

She dropped her trench coat to reveal her body to him. She was wearing a red silk piece of lingerie — see through. He could see her nipples. Rock hard. Her pussy. Waxed bald. Her flat stomach, her amazing legs.

The Lonely Freak Delusion – [Ff][inc]

I can almost guarantee that every adult you know is operating under the same basic misunderstanding. Let’s call it the Lonely-Freak Delusion. All of them, your boss, your parents, your friends, share this delusion: they all think that *they* are uniquely, or at least unusually, messed up, while everyone else has got their shit together.

This conclusion is so obvious, so natural, that it takes concerted effort and training to overcome it. Everyone you know is fucked up, just as much as you, and yet they *all* think that everyone else has their ducks in a row.

Let me show you: here is the subway and here comes the train, kicking up little puffs of dust in its wake. The doors slide open and we glide silently into the carriage. It’s late on a Saturday afternoon and most of the seats are vacant. This is George. He is 37 and works in the building trade. He wants, more than anything, to share his wife of ten years with another man. Sometimes he thinks of particular men: his boss, his best friend, his father, but mostly the men are faceless. Just cocks with which to ravage and degrade Jenny, his wife and his best friend in the whole world.

The Youth Hostel Dorm [MF, oral, mast]

*I have started a little sexy story blog, and this is my first post. This is also my first post here, so be gentle. Constructive criticism welcome. Link to my blog in the comments if you’re interested in reading more.*

It was 1am when Samantha got back to her room, but all the beds were empty. The hum of the fan in the bathroom replaced the intimate sound she’d come home to last night– the sleeping breath of her youth hostel bunkmates. They had hired the room for three nights, the six of them quickly getting to know each other better by sharing this little space. But it looked like tonight they were all out later than her, except for the one person having a shower.