[M]e and my large breasted [FF]riends

Before I entered my senior year of college, I was introduced to a girl from my hometown who went to the same college as me. I had actually met Emily a few years before in youth group, but didn’t remember her. She knew a bunch of the same people I knew and we met up at an event the local alumni chapter was having. We quickly became friends and frankly at the time, I felt little to no attraction to her. She was a short girl, probably 5 feet tall and a bit on the heavier side. But she had without a doubt in my mind the largest tits I have ever seen.

We hung out a few times that year at school, but she was super immature. She still acted like a high school kid and was very far behind sexually. She only kissed a couple guys by the time she left for college and had never done anything beyond that. At that point in my life I was not ready to dive into that complicated pool. But shortly that would change.

[ff](mtf), Unexpected Interest [slow build][kink][tender]

Hello, and welcome to my wonderful wall of text. For boarding right to the sexy bits, “***” has been provided for your convenience. If you have the following sensitivities or turn offs, please take advisement that MyPoisonIsReddit is not responsible for any injury or suffering that may occur:

All the consent

D/s, Mistress/Slave

Impact Play

Anal Play

Degradation/humiliation (S*** mentioned)

Biting/Marking

Bondage

The Trans Agenda(TM)

Ironic Catholicism

My horrible sense of humor

This is the story of one of my most recent partners. As a bit of background, I’m a transgender woman. I started hormones a year ago, as soon as possible after my new insurance kicked in and a little after I turned eighteen. I’m tall, average build, and have some gentle curves and perky B cups. My hair and eyes are both a dark brown, and my hair is wavy and shoulder length, with natural red highlights. My genitals are still in their original configuration, although it’s become shorter and plumper, and I have a Midwestern accent that almost never comes out, but my domme tells me it can be sexy when it does.

Lily’s Quest – Part Two [Mf][oral][fantasy]

Hey! I’m back with chapter two of this smutty fantasy story. Looking for as much feedback as possible, so if you leave a comment with your thoughts, I’d be very appreciative. Hopefully, this isn’t too long for you folks.

***

Chapter Two – The Company of Garrello Ostinar

Lily walked down the wooden flight of stairs and into the tavern’s food hall. The hall was filled with about twenty or so folk, most of which were men. Eyes all over the room looked at her, some stealing quick glances whilst others stared obviously. One man, sitting on his own near the front, had a devilish grin painted across his face as he drank up Lily’s petite body. Her insides fluttered with excitement from this new form of attention.

She returned the devilish man with a faint smile, and then walked over to the tavern bar. The only two people seated at the bar were two peculiar looking figures: one a slight-built man wearing a long turquoise cloak, and the other a bulky brutish man, wearing a battered looking breastplate, and a longsword clasped to his waist. Both the men where murmuring amongst themselves very quietly, clearly not wanting to be overheard. Lily thought better of it than to seat herself next to those men, so she sat several seats along.

Lily’s Quest – Part Two [Mf][oral][fantasy]

Hey! I’m back with chapter two of this smutty fantasy story. Looking for as much feedback as possible, so if you leave a comment with your thoughts, I’d be very appreciative. Hopefully, this isn’t too long for you folks.

***

Chapter Two – The Company of Garrello Ostinar

Lily walked down the wooden flight of stairs and into the tavern’s food hall. The hall was filled with about twenty or so folk, most of which were men. Eyes all over the room looked at her, some stealing quick glances whilst others stared obviously. One man, sitting on his own near the front, had a devilish grin painted across his face as he drank up Lily’s petite body. Her insides fluttered with excitement from this new form of attention.

She returned the devilish man with a faint smile, and then walked over to the tavern bar. The only two people seated at the bar were two peculiar looking figures: one a slight-built man wearing a long turquoise cloak, and the other a bulky brutish man, wearing a battered looking breastplate, and a longsword clasped to his waist. Both the men where murmuring amongst themselves very quietly, clearly not wanting to be overheard. Lily thought better of it than to seat herself next to those men, so she sat several seats along.

Who wants noodles? [Group]

So, I’m a guy. A female friend of mine came to visit me in the middle of the night with a girl she had recently met (and for added spice worked at a sex-hotline). They wanted to crash my place for a couple of hours to wait for their ride out of town. They had woken me up so I just sat on my bed chatting with them. My friend came to sit on the bed with me and, before long, there was touching. The other girl was using my computer at the time. Things got pretty heated and after a while the friend saw what was happening and came to join the fun. That’s when it turned bad. The thought that this fantasy of every guy might be coming true hit me like a ton of bricks and … I don’t know. I panicked.
I sat up and said: “I’m making noodles. Who wants noodles?” I jumped off the bed and walked straight to the kitchen, feeling their “What the SHIT!?” looks on my back. Then I just stood in the kitchen looking at nothing and ended up making noodles with added tears. They left soon after.

[MF] Finally knitting class leads to me getting laid!

Hello, here to share my story. Weeks in the making!

I’m 27M, tall and lanky, blonde hair, blue eyes, somewhat socially literate but pretty shy and dorky. A few ex girlfriends but having trouble meeting people since I left college. Tried online dating with little or no luck. Someone on Reddit (jokingly?) said you can “slay pussy” at a knitting class so I decide to try it! $50 on knitting supplies at Michaels and $80 for a 12 week knitting class (of all experience levels) at a local tech college. Here we go!

I show up for my first class, early. Hoping it’s filled with manic skinny redhead girls who love knitting and are ready to throw themselves at me. The instructor is an old woman. Everybody filling in is an old woman. The classroom is like 70% women in their 50-70s. One other guy, an older man with grey hair. I’ve made a terrible mistake.

One eligible woman walks in. She’s a brunette, short, a little heavy, very cute face, maybe in her late 20s, and a massive chest. She walks in and makes eye contact with me. I eye beg her to sit next to me. Instead she sits in the back. Crap.

I want to share some of my experiences. First story [Group] [MF] [exhibition]

I have been in a relationship for a while now, and recently decided that sharing some past experiences online may be fun. I have always been interested in sex with others, group settings, swinging and the like. As a serial monogomist, I had some experiences, but always wish I had chose to do a little more.

First, some background.

Two re-occuring people will be D and J. D is a longtime best friend (male), J is his HS girlfriend he married quite young. My first story involves my first real slutty girlfriend, T.

T had a lot more experience. She was the first one to let me try anal, wich turned out to be a major kink to me. We had met through Yahoo chat (it was a thing), in the locals section. I miss the anonomous chatting with people who were generally somewhat local. It always turned me on.

T had decent breasts, but had an ass to die for. doggy style her pussy and ass were always exactly the right height. She is one of two people I have ever felt like my dick was truly buried all the way in. Expecially in her ass.

[MF] Getting my first blowjob, after prom, and in a pool.

This got a little long scroll down to the ***** if you’re just here for the sex.

My last story seemed to strike a bit of an unintentional nerve, and that was the last thing I was going for. So let’s maybe jump back to the summer after high school graduation and see if we can all agree that high-school-summer-sex was/is just straight up the best. Also, (spoiler alert mother fuckers!) this ends with just a blowjob. But when you’re 18, sitting in a pool at 2 am, with a girl you’ve crushed on since you were 12, and that warm midwestern night air is blowing through the trees, a clumsy, awkward, and ill-conceived “just a blowjob” can be the bees fucking knees.

I grew up in a suburb of Des Moines in a highly religious family, and even though I was pretty popular, decently well liked, and alright looking, I didn’t actually have sex until I went off to college. It wasn’t that I thought Jesus cared about what I did with my dick, it’s just that I liked my parents (still do) and they kind of expected I wouldn’t have sex in high school- not that I had tons of chances.

Making the most of a tryst. (Part 1) [MF]

The Set Up

 

Coming up on a year ago, my friends and I got tickets to a massive country music festival in the middle of nowhere. It would be a three day partying shit show that happened to have some big name artists playing in the evenings at the heart of the location. Our plan was to tent camp along with ten thousand other festival goers in the summer sun. We made our plans and packed our supplies and away we went. We got in around midnight the night before the festivities began and set up camp by lights of our cars and began some drinking games.

 

[FM] [cheating] My Grad School FWB

So this story takes place a couple of years ago when I was in grad school. At this time I was married for a few years, and had been having some sexual frustrations with my wife. I met Jenny because we took the same train from the city to the suburbs, but at different stops. She went home to her boyfriend, and me to my wife. We became quite good friends over a couple of years, along with a group of 6-8 other classmates that shared the train. The group started hanging out together on the weekends quite a bit, but my wife never came because she worked a night shift on the weekends. So it would give me something to do. We’d go out quite regularly, with nothing untoward happening. Along the way, Jenny broke up with her boyfriend and moved into an apartment by herself in the city. One Saturday the group was meeting up at a Mexican restaurant for dinner and drinks, and somehow due to completely random logistics the plan became for me to meet Jenny by the train station and walk over to meet everyone else. This wasn’t totally out of the ordinary, but not a common occurrence for her and I to hang out alone, just the two of us. Now, Jenny was about 29 when this story happened, and I was like 27 I think. Jenny made great money in her job, and spent a lot of it on high fashion and always looking her best. So I was a little surprised when I met her outside the train station and she was wearing a t-shirt and jeans. One thing I did notice was how her tight t-shirt accentuated her big tits. I always could tell that she was a bit top-heavy, but she dressed very professional and classy, so they were never quite on display as they were that night. We hugged, and I could feel them press into me, and I was instantly hard. I felt bad for sexualizing a close friend, but damn those were some great titties. Jenny was a little bit shorter than me, probably about 5’9″, had a great pair of DD’s (as I would later come to find out), and a body sculpted by being a barre method instructor after her office job during the week (also something I didn’t know at the time). She had short red hair, and a cute face. In reality, on equal terms, she was probably a little bit out of my league, but she was a couple years older, just out of a recent breakup, and somehow we were on the same playing field around this time. It made sense. So we went to meet the group for dinner and drinks and had a few margaritas at dinner, nothing crazy. Randomly, one of the group of friends had some out of state coworkers joining us, a dude and a college student intern girl. Come to find out she was bisexual and a bit crazy, but on first glance didn’t really stand out or anything. So the night wears on, and we decide to go to a college bar for some reason. I have no idea, really, I think it was the one guy trying to show his work friends a good time. So we end up at a notorious college bar type of hang out in our city and are dancing and drinking the whole time. I’m quite drunk, Jenny is quite drunk, intern girl is quite drunk. In my altered state, I figure why not flirt a bit with intern girl? No harm, right? I’ll never see her again. So we are dancing pretty close in a wall-to-wall mass of 20-somethings in this shitty bar, and I get closer and closer, eventually wind up putting my hand in her back pockets while we dance, her grinding on my leg and clearly getting frisky. I kind of lost track of time around this time, and as it gets later and later, people from our group tap out. Again, my wife is at work, so I have nothing to lose as long as I’m back by 7am or so. And at this time I had no real intentions, just having a good time getting super drunk and dancing with some essentially random college girls. Good times, no harm. It winds up being just Jenny, myself, and college girl. We are all three dancing with each pretty closely at this point, mostly with the college girl at the center of attention as it was a little weird for me an Jenny to dance together, we’re just friends. But things are definitely getting hot and heavy, and the booze is in full effect. Then, college girl leans in and asks me if me and Jenny are together, and I respond with a laugh that no, I’m married. She seems shocked, says that Jenny and I were all over each other, and that she thought we were dating. She says something to Jenny that I can’t hear, and then back to me and says she doesn’t want to get in between the two of us and that she’s headed home for the night. Weird. My alcohol laden brain didn’t notice it at the time, but I think Jenny told college girl to scram so that her and I could be together. Well, at this point I am very drunk, very horny, and very much alone at 2am with a cute, single friend of mine whom I know very very well. And we dance. Hard. In the middle of everything it didn’t seem that crazy, but we were grinding hard, sweaty bodies up against each other, my hands in her pockets, her grabbing my ass. The whole thing, it was hot, sweaty, and fun. Even at this point, I thought this was just a little flirty fun, no lines had really been crossed, and that we’d just turn in at some point and go our separate ways. The bar announces last call, and Jenny and I leave. At this point we’re holding hands, I don’t know who started it, but it felt good, and after all that dirty dancing seemed relatively tame. Still didn’t think any lines had been crossed, necessarily. As we leave the bar, Jenny takes me by the hand and says she has something she wants to show me. We walk about a block or two to the beach, and sit down. We talk a little bit about her breakup, she asks me how things are with my wife, and the topic of conversation goes to how hot and heavy things got back at the bar. At this point I figure out what’s going on, that here I was sitting very close (it was cold out, we were snuggling for warmth) to a hot, single friend. And we’re talking about how fun it was to get all up on each other. Light bulbs go off in my head, and I make a decision. Yes, I will pursue this. I made the decision to cheat right then, right there. See, my wife and I were in a verifiable dead bedroom after just 2-3 years of marriage, in our mid-to-late twenties. Sex was about every other month, and only begrudgingly. This from the girl who fucked me the very first time we met, and exhausted my entire condom supply in the first weekend we met. Down to nothing. So I was frustrated, depressed, confused, and felt just a little shitty about myself from all the rejection. And here I was. So yeah, I made the call in my mind, that I’d do this. She was laying down, I leaned in and said something to the effect of “let’s pretend this isn’t real, just for tonight, and it’s all a dream, then we can wake up tomorrow and return to normal.” And with that we kiss, gently at first, and then more passionately. My heart was racing, and I realized we were not nearly as drunk as I first thought, it had been a long night and the alcohol was wearing off for both of us. We made out right there on the beach, and I’ll be damned if it wasn’t romantic as fuck. And, at this point, still not all that irrecoverable as far as lines crossed. Making out isn’t not cheating, but it isn’t that bad either. Jenny gets up, grabs my hand again, and leads me back to the bar. We are in a tunnel under a road, and I stop her and spin her around again, kissing passionately. But now, we have a little bit of privacy in the tunnel and more mobility as we’re standing. So I reach up her shirt and start to massage her surprisingly huge tits. I ask if this is OK, and she says yeeees, like letting out a sigh. My hand wanders down to her jeans where I unbutton the top button, and spin her around so she’s facing away from me. I’m nibbling on her ear and neck while I reach down in her panties to feel her wetness. To my amusement but not necessarily surprise, she is cleanly shaven (smoooth) with a little landing strip and wet. I mean, dripping wet. I was surprised by this, and made a comment, and she replied something like “well what do you expect, you’re hot!” And I was so instantly turned on by this because it was a woman expressing attraction to me again, something I hadn’t been getting in my marriage. And it set something off inside of me, I grabbed her hand and shoved it down my pants to feel my rock hard erection as I pet her soaked pussy. I only brought my hand out for a moment to taste, and that drove her wild. She reeled away, spun around, and fixed her pants, kissed me deeply, and took my hand again and led me to a cab about a block away. The cab ride to her apartment was awkward, as it was a moment to collect ourselves and fully realize what we’re doing. Nothing happened in the cab, and as we got to her apartment and she led the way we just chatted casually about nothing. We knew what was going to happen, but it seemed very relaxed. As soon as we got inside her apartment, though, the switch flipped again, and I pushed her down onto the couch and quickly got her pants and panties off. I immediately dove in, lapping up her wetness and taking in the whole experience. I love eating pussy, and she had a fantastic pussy to eat. I was thrilled. We clumsily kicked off the rest of our clothes and made our way to the bedroom. Now we’re both naked, but I am fixated on going down on her, and continue licking her up and down, managing to get first one then two fingers inside her. Around this point I can see she’s really enjoying this, and I start to make a come hither motion with my two fingers while I suck on her clit. I mosey on up to her ample breasts and suck each of her nipples for awhile, and manage to hit just the right angle with my fingers and now my palm against her whole labia and clit, quickly going up and down, pressing just hard enough. She loses it, convulses, and squirts all over the bed. And she was a gusher, making a huge wet spot from her orgasm. My mouth was latched on to her nipples while this was all happening. Her body relaxes, then she sits up, and asks what was that? She apologized for squirting, saying that had never happened before. I told her not to apologize, it was beautiful, and I had a ton of fun giving her that first experience. I moved up and cuddled her gently, as she came down off her orgasm high. We were chatting a little bit about how crazy this was, and this and that. Then she says “your turn” and gets up, and tells me how much she likes sucking cock, and how she’s really good at it too. I’d kind of forgotten about my own pleasure being so wrapped up in her orgasm, but now stood at attention and received the best, sloppiest, deep-throatiest, blowjob I’ve ever received, before or since. This woman was a real pro at this, and was very very motivated to return the favor. As I filled her throat up with what was probably a huge load, in what has become one of my most replayed spank-bank moments of my life, she stared at me deeply in the eyes with a huge grin on her face, and sucked me dry. It also struck me how absolutely cute she was, and how awesomely dirty. She sits up, we cuddle, and she tells me how if I were her boyfriend she would ride me everyday. We share some kinks and fantasies, hers being used freely like a sex doll, and mine in taking her from behind in the school library, between the shelves. But at this time, we’re both pretty spent, and it’s nearing 5am when I could catch a train back home. So we kiss one more time, and I hastily dress after realizing that I had just cheated on my wife. She’s laying in bed, I kiss her one last time, and throw the sheets off one last time to see her gorgeous naked body, and leave. I ran to the train, missed it, and caught a cab home. Got home just in time to beat the wife, who had no idea I was out all night. Me and Jenny didn’t fuck that first night, just didn’t come up, but if there’s interest I’ll tell the story of the first time we fucked and did anal, ass-to-pussy, and creampie. She was fun, and I’ll never forget Jenny. We filled a need each of us had in that one specific time in life. She’s married now to some dude, and lives in a different state. We lost touch along the way. And me, I’m still married.