[M]y first sexual encounter with my Christian childhood [F]riend

This story probably really starts back when I was 13, but really picks up a few years ago when I was 18, skip to the break if you don’t want the backstory. I grew up in a very Christian home where sex and anything around that is supposed to be great, but saved for marriage. So that was how I went through high school, dating a few girls but never going passed 2nd base because I didn’t want to ruin my future relationships.

Now I had a friend named Anabel, who everyone called Anna, that started attending my church a when I was in Grade 8. We both graduated from different elementary schools and but lived in the same area so we went to the same high school. Because we were already friends from our church, we brought our two friend groups together and that combination became my main friend group through high school. Throughout those years, I never thought of Ana romantically, even though I knew she had a crush on me at one point. She was pretty cute, but just not a good personality fit, plus she was one of my closer friends and I didn’t want to mess that up. So we both graduate and begin university at two university’s in the area and I still see her often enough at friends parties and church events.

[MM] Confirming my bisexuality

I wrote up this story for PMs with some people I’ve been chatting with and got good feedback, so I thought I’d share it here :)
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So my first girlfriend broke up with me in my third year of college, about eleven years ago now when I was 21. I’d known for years that I was bisexual but never acted on it in any way so after that I decided it would be a good time to start experimenting & I started looking online. This was still the relatively early days of internet dating so I had a few false starts there (some weirdos out there), but eventually I got talking to this guy a year or two younger than me who seemed cool so we agreed to meet up. He was gay but not out, I told him I thought I was bisexual but hadn’t been with a guy before. I was a little old-fashioned about it I guess because we went to see a movie first. He was a cute, 5’6″ asian guy with a nice smile and a great body (he did some modeling a little later actually, which I’m pretty proud of!) I knew right away I was attracted to him but the whole experience was still so new to me I didn’t really have any clue how to make a move. It was kind of a thrill walking around town with him though, looking to everyone else like just a couple of college guys hanging out, when really we wanted to fuck each other. Anyway we were chatting about movies and I asked if he wanted to come back to my room to watch a DVD. A little clumsy but he said sure so we went back to my place. At that time I had a college apartment with a couple of other (straight) guys, neither of whom I was particularly close with, so I was a little worried about what they were going to think, but neither of them were there when we came in thankfully. The door to my room was pretty solid & had a lock on it so I felt a little more comfortable once we got inside. I put the movie in & we watched about 10 minutes of it before I couldn’t wait any longer to make my move. I was still so nervous because I’d never done this before, I still considered myself just ‘curious’ so I had no idea how I was going to feel if I went for it. What if I saw him naked and suddenly found I wasn’t interested at all? Finally I just put my hand on his thigh and started gently caressing. It felt like I was being so awkward but as soon as he turned and looked at me I could see he was into it so I reached forward and kissed him. I’d kissed a guy before as a high school dare so it wasn’t a completely unfamiliar experience but never anything like this: instantly we went into full on passionate making out like we’d been lovers for years. With a thrill I realized it was really happening and I was about to have sex with a man, and I felt myself get hard in seconds. He started touching my chest over my shirt and I knew I wanted to see his body so I reached over and pulled off his shirt. He was in great shape so I spent a wonderful few minutes running my hands over his body. It was incredible experiencing the difference between a woman’s body and a man’s this way for the first time, feeling his strong firm pecs and hard abs where before I was only used to feeling softness, with him still kissing me gently the whole time. We hadn’t discussed who would be the top or anything like that beforehand, but I got the feeling he wanted me to lead so I pushed him down onto the bed and leaned over him to begin kissing his stomach, licking his nipples, feeling the muscles of his shoulders, and just exploring his whole body. Finally I reached down and felt his hardness through his jeans. Before I even met him I had had the burning desire, if I was going to have any experience with a man, to feel a cock in my mouth. So I couldn’t wait any longer and unzipped his pants, he pulled them off for me and there was his pretty little hard dick. He was only probably 4 inches or so but I didn’t mind, for my first time; I would have been a little intimidated to start out with a monster cock! I moved down and took him into my mouth. I didn’t know what to expect – would dick taste weird? – but he just tasted like good clean firm skin. I ran my tongue up and down his shaft and began gently sucking him. He stretched out on the bed, totally relaxed and I kept working his cock, listening to his quiet moans. Feeling him run his hands through my hair and gently push my head up and down was intensely hot. I felt like I was just starting to get into it when suddenly I felt my mouth filling – at first I thought I was just feeling my own saliva before I realized he was cumming in my mouth. I stayed on and took his whole cock in my mouth and sucked down his whole warm salty load while he stretched out and shuddered. After that I slowly licked his dick up and down for a few minutes until he was soft again. I sat back, not sure what the etiquette was here – I had a hard rod about to bust out of my pants and I desperately wanted to fuck him, but did I have to wait a little until he was ready? Fortunately for me he didn’t want to wait at all, he moved over and took my pants off and started returning the favor. My dick is a lot bigger than his was (about 7″ and pretty thick) but he didn’t hesitate; I lay back and he started jerking me and teasing the head with the tip of his tongue. I had actually never had a blowjob before (first girlfriend didn’t do that, boo!) so this was a new experience for me and although it was hot and he kept me rock hard, it kind of tickled and I didn’t think I was going to be able to cum from it. So instead I looked him in the eye and said “I want to fuck you.” He looked back and said “Ok” and turned over to lay face down, ass up. He had an absolute peach of an ass, great firm ass cheeks and nice strong thighs. I put a condom on my cock and lubed it up, put some lube on my fingers and started probing his asshole. His ass took my fingers with no trouble at all so I just moved over and went for it. I was so excited I thought my heart was going to stop as stood over his legs and lowered myself to guide the tip of my cock to his asshole, and I slowly eased it in. He took the tip with a little moan and I pushed my whole length into him, letting out my own low groans as I began slowly sliding my cock in and out of his ass. Nothing had ever felt so good or so tight. I wasn’t sure how hard and fast to go at first, I didn’t want to hurt him but between moans I heard him say “fuck me”, “fuck me harder” and I began thrusting into him again and again. In a minute sweat was dripping down my chest and I was in ecstasy slamming my cock into his tight asshole, slapping my thighs against his cheeks. I remember even in the midst of all that, realizing “It’s official. You’re a fag now”. In another minute I could feel myself ready to burst and I pushed myself all the way in, balls deep in his ass, and blew a huge load with one of the longest, most intense orgasms of my life. Afterwards, that was that and it was getting late so he headed home. I walked out onto the street outside the apartment, and I couldn’t see anyone around so I got a thrill from giving him a quick kiss and a squeeze on the ass as he walked away. We tried a couple other times to make plans to meet up again but it never came off, but I still think about that night all the time.

Catching up with an old high school classmate over Thanksgiving weekend [MF]

For those in the states, we all know thanksgiving week/weekend is everyone’s unofficial high school reunion as everyone is back home from wherever their life has taken them….and that’s how this story begins….

I was at the bar Wednesday night seeing a bunch of old friends talking about the good ole days and what everyone has been up to, when _she_ walks into the bar, I’ll call her Sarah for purposes of this story. We were always friendly back in school but never really hung out since we had different circles of friends, and I hadn’t seen her since the summer we graduated. Long story short we chatted up for a few, she had grown into a very cute woman , long brunette hair, medium bust, but a great ass that I never knew she had, we said our goodbyes and that’s all I thought of that.

Back out on Friday we ran into each other again, this time with a smaller crowd and got to spend some more time talking 1-on-1. We talked about what we’d been up to , hobbies, relationships and found out we shared similar histories both of us had had long term relationships that just didn’t pan out and hadn’t found the one yet. The drinks kept coming , our chairs kept getting closer and she asked if I wanted to go to another bar that had a DJ and dance floor. Of course I was in.

[MF] Becoming My Landlord’s Pet (Part Fourteen)

My tongue flicked up and down on the asshole presented before me, aided by Michelle’s hand spreading the asscheeks of this stranger, and pushing my head deeper.

Emboldened by the moans coming from the girl in front of me, and curious as to how tight her belt may be, I opted to slip my tongue south and see if I could get a taste of what I imagine to be her dripping pussy.

Instead, my tongue tasted metal and a set of balls.

I let out an audible “ohhh”, that was half whimper and half human. The first time I ever remotely slipped out of puppy headspace as my lips now kissed a set of smooth testicles, framed by the metal cockring. I slowed down. Processing what was before me was so overwhelming that I ceased being able to think and act. The scents and sounds and breasts were all female, so this *puppy* before me having a locked cock was such an unexpected development I had to take a second to realize there was what I imagined to be a gorgeous, thin, and kinky trans female puppy sister with me.

“You two are mischievous, aren’t you?”

Brittany’s New Puppy: Beginnings [f] [bst]

Brittany awoke not with a bang, but with a whimper. Softly groaning to herself, she slowly slid open her eyes, rolling over onto her back to stare up the ceiling.

Light streamed through the window, causing her half closed eyes to squint even further. With a great force of will, Brittany forced herself to roll her head and open her eyes just enough to acknowledge the time. 9:53.

She sighed, knowing that with this new found information her body wouldn’t allow her to rest for long. Though it was a Saturday, Brittany’s mind couldn’t justify wasting the day lounging in bed. She was a doer, and the furthest thing from complacent.

Sitting up slightly so her head was just barely resting on her pillow, Brittany noticed that the house was unusually quiet. Her still groggy head spun for a few seconds before remembering that her sister was receiving an award for a writing competition, taking both proud parents along with her. At 19 Brittany had just begun her college experience, and wasn’t overly concerned with winning any awards. She was content to simply stay afloat.

Sex with a Stranger while on a Relationship Break [fM] [oral] [mast] [squirt] [cheat]

Tim and Sasha had been dating for six years and their relationship was glorious. They had the kind of sex that made their friends jealous — couldn’t keep their hands off each other. But, as with all things, time wreaked havoc on the relationship and by year six, they were in a state of never ending drama.

A break up was inevitable, but they were attached at the hip and couldn’t end things.

While Sasha was in Texas for a work conference, she texted Tim and told him she’d hit her limit with his indecision and needed a break. He told her he understood. Of course, that wasn’t the answer she wanted to hear. She wanted to hear him say he was still fighting for the relationship.

“Fine, then,” she responded.

A few hours later, after she cried her eyes out, Sasha broke into the minibar and drank nearly every airplane bottle she could get her hands on. She headed down to the hotel bar and ordered a Diet Coke.

A man approached. Someone from the conference who worked in the LA office. He was smooth, well dressed, handsome, in shape. All the things Tim wasn’t. And, of course, he was a high level exec.

Marine gang-bang in Puerto Rico when I was a slutty Corpsman [Group]

Hi Y’all,

Here on Thanksgiving I thought I’d share a story (long one, jump down for the good stuff) of a very memorable Thanksgiving that took place when I was in the Navy. For those that don’t know I was once a Navy Corpsman back in the mid 90s (yes I’m old). One of the places I was stationed was at Roosevelt Roads Naval Air Station in Puerto Rico (when it was still open, don’t ask me my opinion of Puerto Rico unless you want a very honest opinion). I worked at the Naval Hospital and lived in nearby Fajardo in a pretty nice apartment tower called Dos Marinas.

One of the least popular things to do in the Navy is pull Duty. Duty means you have to show up to work as normal and once your day ends you go on Duty which means you sit and become the hospital answer desk for 12 hrs until the hospital comes to life again the following day. If who you work for is nice they’ll let you get some rest once you come off Duty but in my case I had to go back to work as at the Internal and Flight medicine clinic. That next day happened to be Thanksgiving but there was a group of Marine helicopter pilots off the USS Wasp needing some physicals. The Wasp which is essentially a Marine troop carrier had pulled in for refueling and R&R. Because of this I knew there were going to be a ton of Marines everywhere looking for fun and as a burgeoning slut I wasn’t about to miss that opportunity.

[MF][anal] having my asshole fucked and filled with cum for the first time

hey everyone!
This story is about the first time I, obviously, had cum on my face.
For backstory, I was 16 (he was 18) when this happened. we were in a car after a movie. we had been rubbing each other a little during the movie, but not much. He basically asked if I would give him a bj, and he would eat my pussy in return.
keep in mind that i’d never had real sex or anything before this point. so, we drove over to his house. it was a 7-9 movie, and his parents were gone. we immediately went to the bedroom. he said “do you want to do something really naughty?”, or some word of that nature. being the 16 y/o girl I was, very wet and ready at the time, I was pretty much up for anything. he told me that he wanted to do anal.
so you can imagine what it was like, here are a couple details.
I’d never showed anybody my vagina before. he wanted to see my butthole? it was embarrassing. I was super insecure about that part of my body for obvious reasons.
My butthole was SUPER tight. I knew because I had tried to finger myself a couple times before, but it was hard and pretty painful so I gave up. I also knew the feeling – it felt like I had to shit the entire time. so I wasn’t a fan of the feeling, but it sounded naughty so I said “fuck yeah”, albeit nervously.
I ran to the bathroom, emptied my bowels, cleaned my hole up a bit, and went back in. he was playing some sort of catchy rap music. he told me to get naked and bend over. I took off my leggings and my panties, nervously bending over and exposing my asshole. he admired it for a minute. then, he spat on it a few times, getting it nice and wet.
this was my first time, but not his. i’d played with my pussy/ass before, but this was on a whole new level. he started by licking it. the perfect combination of rimming and eating the inside made it feel incredible. he then started fingering it, middle finger first, slowly in and out. I was a bit more relaxed, so it went in and out easier.
“ready?” he said. “no”, I replied, smiling a little. he knew what I meant. He grabbed a little lotion, applying it to my butthole, and began rubbing the hole with the tip. he slowly moved in, making gradual progress. he seemed to hit a “wall” a couple inches in. he stayed at that depth for a few minutes. as he would take his cock out, a couple farts would occasionally leave, which were super embarrassing, but neither of us minded that much.
we were eventually to the point that it was mostly in (about 5″). it felt incredible. it still felt like I had to shit, but I kinda liked that sensation, and I could tell it was mutual. he fucked straight for about five minutes, really managing to open my ass up. by this point, I got used to the queefing that was occurring (still embarrassing!).
he informed me, on taking it out, that it was “wide open for me”. I could feel air flowing in and out, my ass exposed to the outside air, which felt kinda good.
he told me that he was gonna cum as we relaxed for a minute, my ass still in the air, him rimming it a bit, fondling with his fingers, etc. I told him he could, but I didn’t say where, so he assumed I was okay with it. he stuck the cock back in my ass, rubbing my pussy, and came. that went on for about fifteen seconds. I could feel it sliding down the inner edges of my ass. it felt very good, and it seemed to fill me up.
he then told me to “fart it out”. I went into the bathroom and sat on the toilet, and he followed me, which was embarrassing again but I didn’t protest. he also requested that I turn around, so he could see it come out of my ass. for a good five minutes, I farted the cum out.
honestly, it was one of the most shameful and embarrassing experiences I’ve ever had. but that was the fun part. i, the shy seeming yet slutty girl i was, loved the feeling of being shamed and embarrassed like that.
thanks for reading! xoxo if you have any questions, comments, or wanna talk/rp, pm me!

Fucking Kristy in her Bed – Pt.2 [MF] [affair] [cum] [piss] [anal] [oral] [mast]

A week after Derek cheated on his long term girlfriend, Heather, with his gym friend, Kristy, he felt horrible angst. Would she tell? Would he be able to live with himself?

Derek and Heather frequently ran into Kristy at the gym and they continued to run into her for weeks and weeks. Kristy and Heather always got along and his worse fear is they’d bond and Kristy wouldn’t be able to hide the truth from her new friend a moment longer.

Eventually, Derek caved and texted Kristy.

“I’m such a hot mess,” he wrote. “I am so nervous that you will tell Heather. I believe you when you say you won’t, but I just need to hear it again.”

“Why don’t you come over and I’ll tell you to your face,” Kristy responded.

Derek knew what this meant — they were going to fuck again. And honestly, he couldn’t wait. He’d been thinking about fucking Kristy for almost a month. He’d become a little obsessed with her, jerking off to those slightly revealing Facebook photos of Kristy in bikinis or low cut dresses.

“Congratulations on Your Promotion”

“Greta, Mr. Fraser would like to see you in his office today. I have scheduled you in at 4 PM, please do not be late.”

“Oh fuck!” I can’t help but think to myself. When it’s Friday and the boss of the company wants to see you that afternoon, that’s never a good sign. Not to mention that my pervert of a boss has been after me since I started 7 months ago. I knew I shouldn’t have accepted this job when he was flirting during the initial interview, but how could I turn it down? The money was just too good to pass up, especially for an entry level accounting position!

When my husband and I moved to New York, it was a struggle. He’s a writer, but the truth about being a starving artist isn’t nearly as glamorous as you’d think. I had just finished my Bachelors in Accounting, but being a tall blonde woman, people tend not to take me seriously. The fact that my breasts are 34D’s doesn’t help. People don’t see a smart woman when they look at me; they just see a bimbo, which is what I’m sure Mr. Fraser thought when he hired me. But I work hard, and I thought I was doing well, apparently that is not the case though, since I’m afraid I’m about to be fired.