Trying New Things

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The three of us continue to get more comfortable.
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For those of you who may have missed the first two stories in my series, my name is Jessie, and I have always had a particularly high sex drive. However, it wasn't until my mid- to late 20s, nearly four years ago now, that I really pushed the boundaries of my sexuality and enjoyed my first threesome. What made that time all the more fabulous was that it involved my two best male friends who unashamedly gave full vent to their depraved desires on my petite body. Since then, their craving for a Jessie sandwich has not dissipated in the least, much to my amusement, and if not for the fact that one of those friends lived much too far away, we would hook up far more often.

For those of you who must know, I am a thin, 5'5" (and a half!) brunette with brown eyes and slightly tanned skin. I've been complimented on many of my features with different levels of sincerity. I hear a lot about my eyes, though I don't have much to say about them since they're just dirt brown. My hair seldom stays the same, but it's usually about shoulder length or longer, and, while it's naturally straight and brown, I sometimes curl it and very often add different highlights to it, particularly reds. One of the most common compliments I receive is for my mouth, which I can't really explain. I do work hard to keep my teeth straight and white, but the welcoming red lips are something with which I was simply blessed. The oddest one I get is my feet, which I heard for the first time just a few years ago but now more and more guys (and girls) tell me how cute they think my size 5 feet are. All I can say about it is I love shoes and take much thought into my footwear, especially when sex is in mind, so I enjoy the attention.

More than a year went by between my first devil's threesome and the second one, due in large part to the confusing, conflicting emotions I experienced as I came to terms with the fact that a wholesome girl like I had allowed her two best friends to double-fuck her. It was a hot and exhilarating experience, one that I sincerely wanted to relive, but it also felt shameful, like something decent people would never admit to thinking about, let alone doing. In fact, to this day I am still not comfortable to tell even my best girlfriends about some my raunchy group exploits - though the few that I have told think it's entirely sexy. Even as I write this third installment that took place two years ago, I am still on this journey of increasing confidence in my sexuality. For sure, a lot of people would be shocked to know what this professional, educated, attractive (I'm told) woman does behind closed doors!

Not nearly as much time passed until Jason and Leo, my two best friends, were preparing with me for our third threesome. About five months after the second session, Jason was on his way down from my old home up north to my new home down south. This time, it was only that distance that kept us from fulfilling our lust since the wonderful time we had shared that past February.

The first two times occurred when I was back up visiting family for whatever special occasion. There was one other time during that summer where I was in the area, but I think it was ultimately nerves that caused us to fail to pull the trigger that time. On this occasion, Jason decided to take a long weekend just for the sake of traveling down and meeting up with me to team up with Leo, thus making up for that potentially missed opportunity earlier in the year.

Leo and I were eager to get going as soon as Jason arrived late that night, but the long drive had taken its toll on my poor friend. I thought he was going to fall asleep right on my doorstep, and he complained of an awful headache. I don't think he even noticed that I was dressed in black lingerie and matching high heels! Instead of taking him into the living room, I closed up my robe and showed him the guest bedroom. We would still have two full days to fulfill our fancies, so I wasn't too disappointed. I was still a little nervous anyway. I hadn't yet built up the experience I have now, which even still isn't a ton.

Having known Jason for a long time, I knew all he needed was some rest. Surely enough, all three of us were ready to go late Saturday morning. Before the clock had even struck noon, we were all assembled in the living room, my two friends sitting side by side on the couch while I took center stage in front of them.

I always took special care to look my best for these gatherings. It's daunting enough to look good for one boy, so just imagine the pressure of looking good for two. I entered the room to join my still fully dressed partners, myself clad in a little outfit of my own. It was not the black getup I had donned the night before in hopes of a little preliminary fun, but rather what I had picked up specifically for this main event: a very short, pleated red skirt, black open-toe high heels (of course) that were about four inches and a tight white button-down blouse that clearly showed the red and white polka-dot bra beneath, which matched my red thong. My shoulder-length brown hair hung straight down and was dyed a little darker than normal at the time. Thanks to the summer sun, my skin was darker than it had been for our previous exploits, matching well with my brown eyes, which popped, along with my lips, thanks to eyeliner, mascara and lipstick. Leo always told me my eyes and mouth alone were all I needed to seduce a man - or perhaps two men, in this case.

The nerves were still there, but my confidence was definitely in better shape this time around, and I felt comfortable with my friends. The first part of group sex was always the most anxious anyway, as I never really knew how to begin these types of escapades. Once I was in the middle of my own living room, I smiled nervously at my men, thinking of something to say for only a second when Jason suggested I stand up on the wooden coffee table that was right in front of me and give them a little show. As I attempted to come out of my shell, I smiled wider and complied with Jason's request, my heels knocking one at a time against the wood as I stood erect before my boys.

It felt a little silly to put myself on display on that little table that acted as my stage, but the boys really seemed to like it, so my nerves began to finally melt away. I started by pulling the skirt down my thighs and was greeted by a shout of affirmation from Leo. I smiled back at him and pushed the garment down until it fell around my ankles, putting my slender, tanned legs and red thong in full view of my two biggest fans.

In an effort to be smooth and sexy, I tried to kick my underwear off my ankle, but it didn't work. I blushed, and Jason and Leo laughed a little, but I kept my nerve, instead reaching down to pull the red garment off the heel of my shoe, on which the skirt was caught. As I bent forward, Jason said, "Loving the view, Jessie!"

I looked up at Jason, smiling as my brown eyes met his green ones, which were more interested in looking down my shirt. While I wish my boobs were more to talk about, Leo and Jason seemed to genuinely enjoy them, which is all that matters to me. Still smiling, I focused on getting the skirt off my foot before I stood back up again and kicked the garment over toward Leo.

Leo wasn't too interested in the skirt, throwing it away quickly as both he and Jason remained fixated on me, waiting for my next move. I looked back and forth at the two of them as I reached up for my shirt and went to work on the buttons, much to the delight of my friends.

Soon, my blouse was completely unbuttoned, and my polka-dot bra was revealed, eliciting more affirmation from the boys. The whole time, I flashed a grin that was trying to be sexy but probably made me look like a moron. I couldn't help but be madly amused and incredibly aroused as I anticipated the fun I was about to have with my two hot friends who had no qualms about using my body to fulfill our mutual lust.

For the moment, I left the blouse unbuttoned and hanging on my shoulders. I felt a little uneasy because I wasn't sure what to do next. I wish I could have confidently teased my men like a pornstar, but this was real life, not a film. I decided to simply step down from the coffee table and ask the boys to undo their pants, figuring it was as good a time as any to get the party started.

The boys immediately granted my request, quickly unzipping their flies and pulling their waistbands away from their hips, giving me two, long, hard cocks upon which to gaze. Jason followed up by pulling his shirt off quickly. It was plenty obvious that the boys were no less excited than I was! My pussy began to get really wet thinking about what those two gorgeous dicks would be doing to me in just a few moments.

Dropping to my knees, I took a hold of both cocks, one in each hand. Even though it was our third run at group sex, the boys appeared to still be a little uncomfortable with each other, so I had to tell them to stand a little closer. It didn't help that, until recently, they had viewed each other as sexual competitors over me. It's amazing how many problems can be prevented when we just learn to share! Anyway, despite their obvious discomfort, they did as I asked and scooted a little closer. I mean, I know they are both very much so heterosexual, but it's not like I was asking them to kiss! Beside, let's be honest: with the way I was dressed and what I was going to let them do to me, I knew they were putty in my hand, a fact I found to be truly endearing.

I wrapped my fingers around both members as I knelt in front of them on the floor before the couch and leaned forward. I couldn't make up my mind which engorged cock I wanted to play with first! They traded off pretty well, Jason's cock being a little longer but Leo's being a little thicker, both attached to young, thin, athletic bodies. I was in my glory but I needed to make up mind and start somewhere.

I didn't want Leo to think I was favoring our guest, so I opted to suck his cock first, all the while sliding my right hand slowly up and down Jason's shaft. I was delighted to feel how hard Jason was and equally excited by that thick, hard dick of Leo's as it passed my lips and filled up my mouth while I held it in place at the base. Both boys were groaning and moaning in no time as I began to confidently pleasure them at the same time.

The people at work would have never imagined what I was doing in this moment! My head bobbed up and down one friend's prick while my thumb flicked against the tip of the other friend's, giving me an exhilarating feeling of being in control of two stiff erections and holding these strong men at my beckon call. After about a minute of polishing Leo's knob, I switched over to Jason and proceeded to give him the same treatment. Leo wasn't too disappointed that my mouth had left him, given his moans as I stiffly jerked him off instead, his cock slick with my saliva. Meanwhile, my hand gripped Jason's cock, which I held up to my face before flicking my tongue out at the tip of his penis a few times. He grinned and moaned, playing with my hair and begging me to take him inside. With an uncontrollable smile, I beamed at him and then opened wide to fit as much of his long manhood as I could, making him sigh with pleasure as I started to suck him off.

Jason's moans were music to my ears as I fixed my eyes on Jason's hard chest and stomach muscles while my head bobbed up and down, slurping on his shaft. Leo signed and cursed beside him as I stroked his cock at the same pace at which I was sucking Jason. It was safe to say they didn't mind being right next to each other anymore! In fact, I think Leo even inched a little closer, so as to allow me to improve my grip on him while I simultaneously pleasured those two gorgeous phalluses. I felt more and more empowered each time either one of them moaned, tensed or squirmed from the treatment I was giving them.

After a few minutes of sucking Jason's dick, I switched back to Leo and continued in like fashion for a little while longer. Admittedly, I was prolonging the foreplay a little due to the nerves I felt leading up to the main event. Looking back, I don't know why I was still so nervous, since the first two times had been nothing short of blissful. I think more than anything the anxiety was caused by the fact that I had yet to rectify in my mind what I was doing, having sex with two boys at once, which is something good girls don't do and what 99 percent of the world would be shocked to find out I was doing that moment.

All that said, I still enjoyed blowing them both off, my mouth grinning and eyes beaming no matter which of my two sexy friends I was sucking and which one I was beating off. One thing was for certain: those rods were going to be good and ready for my other holes once I had worked up the nerve.

Another moment passed as the boys praised and affirmed me. Then I pulled my mouth and hands away from them and stood up. As I did, I lowered my shoulders to allow the blouse to slide down my arms and fall off my body to the floor beside my feet, leaving only my underwear on my body. My friends, who had been quite vocal a minute before, watched on in silence as I bared more skin for them, nearing closer and closer to the next stage of our evening.

Next, Jason took the remainder of his clothes off, and Leo followed Jason's lead. With both boys beating me to total nudity, my qualms seemed to finally dissipate to the point that I was suddenly eager to get those two sexy guys inside me. As my friends stood up in front of the couch just inches in front of me, their erect cocks seemed to be begging for a piece of me, flattering me as my confidence at last began to soar. With my newfound boldness, I reached around my back and grasped the hooks on my bra, preparing to bare my chest to more than one man at a time for just the third time in my life.

I couldn't control the grin on my face as my bra joined my shirt on the floor, two sets of eyes now glued to my bare boobs. Now in my glory and brimming with confidence, I slipped my thumbs into my bright red thong and pushed the garment down my thin, tanned legs until it fell on its own around my ankles. The boys broke out of their silent stupor to cheer me on now that I was totally nude, expect for my shoes. I smiled and flung my hair back quickly before bending over, my boobs and hair hanging down toward the ground as I carefully pulled my undergarment around my cute heels before tossing it aside, all the while as my boys continued to sing my praises.

Without hesitating, I turned away from the boys and dropped back to my knees, leaning forward over the small coffee table in front of me, holding myself up by my elbows. Jason and Leo needed no instructions. As I looked up, I giggled while Jason walked over in front of me and Leo stationed himself behind me. Leo, having been able to settle in first, got to work before Jason did, crouching down behind me and quickly easing a finger into my pussy, which was already getting wet with anticipation. I looked over my shoulder while Jason played with my hair, both of us watching Leo slide his finger back and forth, in and out of my pussy, making it eager for something bigger and harder to penetrate it. As he fingered me faster, I threw my head back forward and moaned, while Jason took my head in his hands and kissed me. A moment later, one of his hands slid down to my breast and gave it a good squeeze. Leo followed suit, briefly grasping my other boob while he finger-fucked me. It was quite a neat feeling to have two different men fondling my boobs - not to mention while I had a finger in my pussy and a tongue in my mouth! They were masterfully preparing me for the debauchery that was about to ensue, stimulating my entire body that I was ready to be sacrificed on the altar of their wicked, depraved, endearing lust.

I was almost overwhelmed by the foreplay and was practically begging Leo to shove his cock in me before long. Eager to fulfill my request, Leo pulled his finger out of my cunt and then put one hand on my lower back as the other pressed his penis against my sex organ, which was now plenty wet. With one smooth motion, Leo pushed himself into my twat while Jason and I watched over my shoulder.

Now with both hands on my ass, Leo slowly thrust forward while I watched that cock penetrate me until his balls touched my clit. I shuddered, and we moaned in unison as our bodies joined together. Leo commented on how wet I was and immediately began to pump in and out of me steadily within seconds of entering my temple.

Once Leo was in full swing making love to me, Jason turned my head back toward him. "Sorry," I said with a grin. "You know now how worked up I get when I'm having sex." Jason smiled, his cock in hand. The poor boy had waited nearly a decade to get his cock in me, and now that we finally had a sexual relationship, I wanted to give him every opportunity to make up for that lost time. I loved how he, as well as Leo, enjoyed unselfishly watching me have intercourse with another man and how eager they were to share me in our newfound group dynamic. "Put that beautiful cock in my pretty mouth like you always wanted to," I said to him in a sexy voice that sounded much more confident than my previous attempts.

Jason slowly moved his cock toward my mouth, which I held open for him. He had to be careful, as Leo was pushing my body forward over and over again with his hard thrusts into my vagina, making it more difficult for Jason to aim his manhood into my open end. To help out, I held onto the edge of the coffee table, my body propped up by my elbows, and tried to hold as still as possible as Jason finally slipped his phallus past my lips and teeth.

Both boys moaned, Leo clutching my waist and Jason just standing still as I let Leo push me forward and back again, and so making me suck up and down Jason's cock. Occasionally I had to push my long, brown hair out of my face, but other than that, there was little I needed to do, as Leo quarterbacked this play, pumping in and out of my pussy, his balls slapping against my clit as my body rocked back and forth between the boys who penetrated me at either end.

"Sliding you back and forth like a slinky!" Jason exclaimed as I sucked his cock while his counterpart pounded my pussy. Eventually, Jason grabbed my hair and pulled just enough to turn me on but not hurt me, and the boys split-roast me for several more minutes, making me their sexy bitch while my mouth slurped on Jason's cock and my pussy devoured Leo's prick as my friend behind me slapped against my ass over and over again.

After a few minutes, my friends agreed to switch, giving me a moment to catch my breath. I offered to simply swing myself around for them so that they could stay put, which I did, stepping over to the other side of the coffee table before assuming the same position as before with my knees on the ground and my elbows on the coffee table, which creaked a little louder this time after having had my body rocked back and forth on it for a little while there.

"Let me taste that gorgeous cock, Leo," I said before looking over my shoulder at Jason. "And you, show me just how bad you've longed for this pussy." I was as wet as the boys were hard, and they effortlessly slid into either end of me, filling my mouth and pussy. Jason sank his nails into my waist, and Leo held my head in place, and then they just went at it. I was at their mercy, and I loved it.

Jason and Leo didn't bother syncing up. Rather, they held onto either end of me and pumped in and out of the respective hole they were responsible for at that moment. They got really into it too, moaning, cursing and shouting as they pummeled me at either end. It was hard to imagine we were really still just getting started! Their affirmation, not to mention the fact that I was getting fucked in both ends, was so arousing that I was getting closer and closer to cumming already the louder and louder they got, rocking my tight body between their perfect frames. I was oh so close to that orgasm when Jason, who didn't know better, slowed down in my twat and pulled out. I would have cried out in disappointment had it not been for the fact that Leo was doing his best to drill his cock into my throat! A second later, it became apparent what Jason was doing: preparing me for the main event.

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