Jessie's First Threesome

Recently I have found much enjoyment sharing my sexual exploits with strangers online, giving me an outlet for a significant part of my life that I have kept a secret to almost everyone. This platform also allows me to protect my privacy, so it's a perfect situation for me. One of the most frequent questions I receive is how I got started down the path of debauchery. Another common request is a detailed account of any particular adventure I have had.

In fulfillment of both of those requests, I decided to post an account of my first threesome, which occurred right after Christmas in 2013. Being a writer by trade, I look forward to using my skill for something beside work. I will admit, however, that my one friend had already written a story of this account and others, so I did use a lot of his wording and structure for the sake of accuracy and saving myself time and effort. In the interest of privacy, I have assured the men involved that I will not use their real names. Also, for the sake of the flow of the story, I may omit certain hygienic and preparatory details. I will try my best not to exaggerate, though I tend to get excited when recounting the fun I have had in the past.

At this point, allow me to introduce myself. For those of you who don't already know, my name is Jessie. I am currently 29 years old and have a degree in the media field. I am a professional woman whom many would never expect to have the experiences I pursue even as I reach my 30s. I know I have good looks, and while I would prefer to downplay my physical appearance, I know how I look plays a big factor in a story of this nature. Therefore, forgive me if I sound conceited from time to time as I continue.

I take good care of my body, so even at 29 I have been able to maintain a thin frame, but I'll never give out my weight on here. I've been told I could afford to gain a pound or two, though I disagree. I am 5'5" with hair that is naturally brown, but occasionally I like to put some red in it. I have brown eyes, as well, and while I wish I had a better tan, my skin is naturally a little dark, thanks to my Greek ancestry. I have no reservations about using makeup and I regularly get manicures and pedicures.

My story begins 11 years ago when I met Jason. I didn't see him as a romantic interest right away, but I really did enjoy his company and grew to appreciate his friendship more and more as I spent more time with him. I guess I wasn't surprised when I found out years later that he had a crush on me all this time. If I'm completely honest, there was something that kept drawing me to him, even though I told myself I didn't like him "that way."

Less than a year later, I met Leo. Leo was a bit less shy than Jason and more confident at the time. Leo asked me out just a few months later. He and Jason were the only truly trustworthy guys I had met to that point in my life, and after having been taken advantage of a couple of times by less noble men, I was ready for a more committed relationship.

My relationship with Leo continued on for several years, but so did my friendship with Jason. One summer, about five years ago, I grew really close with Jason while Leo was out of town for a couple months. I was finally coming to grips with the fact that I did have feelings for Jason, but I didn't know what to do about it. Eventually, I found out that he was just as conflicted about me, and our relationship became very complicated.

Without going into the long story, I decided I needed to commit to Leo, and when Leo moved away to be with his family, I went with him. However, our relationship got a little rocky afterward. We didn't completely break up, but I did move out, and we were more like "friends with benefits" from that point on.

Jason and I still talked all the time, be it through text or email. Our dirty talk had abruptly ended when I made the choice to commit to Leo, but the sexual element of Jason and my relationship started to creep back in after Jason found out about the change in my status. I welcomed it. Had I still lived in the same area as Jason, I wouldn't have hesitated to sleep with him if the opportunity arose. Through all of that time, I never did anything physically sexual with him.

Maybe it was because I lived far away and the likelihood that anything would actually happen between us was low, but by the fall of 2013, our renewed dirty talk had turned into full-blown sharing of fantasies with each other. One thing about Jason is that when he's really tired, he has no filter. Therefore, he says exactly what's on his mind without seeing any reason to hold back. It was under those circumstances that Jason revealed to me his dirtiest fantasy.

Until that point, I didn't know straight guys really fantasized about teaming up with another guy to have a threesome with a girl. However, I'd be lying if I said the thought never crossed my own mind, especially at the height of my separate involvement with Leo and Jason. When Jason told me he thought it would be really fun if he and and another guy fucked me together, I was shocked, yes, but also really turned on.

The only thing about the fantasy that made me at all anxious was Jason's specific mention of double penetration, which was really a deal-breaker for him, I think. While I totally got a guy's appeal of a girl's getting filled up in both holes, I couldn't imagine it was really all that enjoyable for anyone in real life. For straight guys, they would be way too close to each other, and, for the girl, it sounded painful. Sure, being a girl who is all about pleasing my man, I had let Leo, on occasion, fuck my ass to his heart's content. The more experienced I became with anal, the less painful it was for me and the more I started to genuinely be turned on by it. However, having both holes filled, I could only assume, would bring with it a whole new level of discomfort.

Like I just said, though, I have always been all about pleasing my man. Just like I was happy to let Leo give me anal, a significant part of me was instantly ready to give Jason what he dreamed about, especially since he had never gotten to have sex with me despite a decade of desire to do so. The obstacles, however, were the physical distance between us and finding a second man. Leo was the obvious choice, especially since I no longer wanted to have any type of sexual intercourse with anyone I didn't trust completely, but I couldn't imagine Leo would go for it. Not only was he fiercely heterosexual like Jason, but there had naturally developed a sexual rivalry between the two boys.

In recent months, people have told me that few men would turn down a devil's threesome with me. Perhaps the odds weren't stacked against Jason as much as I thought - not that Jason even knew how seriously I was taking his fantasy. I decided to suggest a threesome to Leo with the excuse that I wanted to try something new to spice up my sex life. After all, we weren't in a committed relationship anymore, so I didn't stand much to lose.

Leo was actually very open to the idea, and thus my excitement grew. The only obstacle now was the literal distance between Jason and me, but having grown up in the same area in which Jason was still residing, a lot of my family lived there too. It wouldn't be too hard to arrange a private get-together under the pretense of visiting family for the holidays.

Jason didn't bring up the threesome fantasy again on his own because he couldn't believe he had confided that thought to me! I played along for the next few days, not mentioning it while I secretly made arrangements on my end to give my friend the fun time with me he deserved. Once Leo and I were set to visit back home for Christmas, I told Jason when we'd be up, so he was happy that we'd be hanging out again soon. It was then that I suggested to him that he, Leo and I get together for an afternoon and give Jason the opportunity to live out his fantasy of having a Jessie sandwich.

I can only imagine what thoughts ran through Jason's mind as I gave my good friend the green light to sandwich me just like he had always fantasized. He kind of downplayed it at first but very carefully did not refuse the offer, naturally. He insisted that no other girl turned him on to the point that he would carry out such a depraved act like double penetration, as if he were defending himself, which he had no need to do. I later found out that he frequently watched double-penetration porn (which I recently have gotten into myself) but he always imagined I was the girl in the middle. I was flattered and further determined to give both boys the time of their lives.

The last piece of the puzzle was a location at which to do the deed, and I figured a motel would suffice, since I would be staying with my parents, Leo with friends and Jason had roommates. However, I still had a lot of friends back home and found out that one of them was going out of town with her husband. Now I saw a better option and messaged my friend to see if she'd let Leo and me house sit for her. She gratefully agreed, having no idea what depraved acts would be committed there.

Over the course of the next couple months, I researched double penetration online. It was discouraging at first because I didn't find a lot of real and positive feedback on the subject, and I began to grow dreadfully nervous. However, through persistence, I came to the conclusion that with a lot of patience, a lot of foreplay and a lot of lube, a sandwich threesome would be a lot of fun for all of us.

The day after Christmas in 2013, Jason came over to the agreed upon location in the mid-afternoon. I was back in the bedroom getting ready while the boys awkwardly chatted in the living room over a couple drinks. They wouldn't get to see me until I was fully ready and presented myself to them in the living room, and I have to say that I knew they wouldn't be disappointed. Jason especially, who had secretly obsessed over me for more than a decade and never so much as got to see me naked, was in for a treat.

There was not a single objection from either guy about what was to take place this afternoon, but that's not to say they were ever relaxed around each other. I can't imagine how uncomfortable they felt as they waited together in the living room for me, but I didn't want to rush my preparation for the most outrageous thing I had ever agreed to do.

Carefully, I put on my make up after slipping into Christmas-themed lingerie, over which I put on a matching knee-length red robe with white trim. A few days before, I had gotten a fresh manicure and pedicure, so my nails were looking perfect. The last thing to do before topping off the outfit with a fun little Santa hat was wearing the six-inch open-toe high heels that were jet black. I knew Jason, at least, would like them, since he always complimented me on my high heel shoes.

Following a series of deep breaths as I looked into the mirror, I made sure everything was perfect. I had slightly curled my hair, which still reached my shoulders. For this occasion, my hair was brown then, fairly close to its natural color. My nails and lips were all a matching red, a color that not only went with the season but always looked good on me, I thought. Finally, I picked up a silver and a gold bracelet and, just as I was about to put them on my wrist, I decided to put them both around my left ankle. I figured they'd be sexier down there. Then I put my shoe back on and, with a couple more breaths, finally turned around and reached for the doorknob.

The living room already seemed pretty quiet before I opened the door, but it went obviously silent when the boys heard me emerge. At first, I just slipped my leg out, the one with the bracelets around the ankle. Then I pushed the door wide open to put my whole body in view for the boys. As aroused as Leo looked, Jason seemed as if his jaw was going to fall off and his eyes were going to pop out. I couldn't help but grin, as I always enjoyed being the object of male attention. Pleasing one of my best friends for the first time made it only better.

With admittedly fake confidence, I strutted across the hardwood floor, my heels clacking against the surface with each step. As I set foot on the carpet of the living room, I only hoped that the boys couldn't tell how nervous I was as I awaited my fate. Yes, I was really excited to fuck two guys at once, but having never done it before, I had no idea what to expect. What helped is that all three of us would be figuring it out together.

I got really anxious at this point, a mix of nerves and excitement. Without giving it much thought, I pushed the robe off, letting the garment fall around my heels, revealing the cute little red outfit I had on underneath. I couldn't help but notice the huge bulges in the boys' pants. I had seen Leo in that condition more times than I could count, but it was a first with Jason and, well, with any two boys at the same time for me. The excitement of having sex with two men at once peaked at that point, and I began to release my inhibitions. Uncertain of what to do next, I suggested we all take our clothes off. I guessed there was no need to draw out formalities, since we were all a little uneasy anyway.

The boys tried to ignore each other as they stood practically side by side and disrobed right in front of me. Leo constantly glanced up at me, while Jason's eyes remained transfixed on me from the moment I exited the bedroom. My heart fluttered with being the attraction as I anticipated the impending fun. Once the boys were mostly undressed, I joined them by using just my thumbs to push my thong down past my knees. Then I let it simply fall to my ankles before kicking it aside, careful to keep my high heels intact.

With my ass and pussy now exposed, for the first time to two men at once, the atmosphere got pretty hot pretty quickly. The boys were now completely naked, their erections poking out as if reaching for me. I couldn't help but notice Jason was a little bigger than Leo. Both boys were cut, and I was well-accustomed to Leo's six and a half inches, but I had never seen Jason's rigid seven inches. Both were engorged and thick. I have never been one to put too much stock in penis size, since sometimes it could even be uncomfortable. However, I had a perfect set right in front of me, and I was sure Jason knew how to use it as well as I knew Leo did.

Still wearing the hat, jewelry, heels and bra, I started to direct the party. Like I said before, significant foreplay was going to be a must in order for all of us to enjoy the debauchery with which we were experimenting today, so I had us all start by sitting on the couch, I in the middle and the boys on either side of me. Apparently my frame between the two of them was enough space for these heterosexuals, and it would have to be as we would all be in close quarters for most of the remainder of the afternoon.

I remember the heat emanating from both boys as they sat on either side of me. The sensations coupled with those rock hard erections right within my reach made me wild with anticipation. Without a word, I took one cock in each of my manicured hands, Jason in my left and Leo in my right. I immediately began to stroke them both, eliciting a moan from Jason and a sigh from Leo. I grinned seductively and looked first at Leo and then lingered on Jason, who really quivered as his patience with me was finally beginning to be rewarded.

My pace increased a bit, my hands going quickly up and down both shafts, from the tips to the balls. Leo groaned and put one hand on my left shoulder, pulling my head down toward his cock and incidentally forcing my hand away from Jason. I just went with it, leaning over onto my right side between the boys and putting both hands on Leo's cock, now simply holding it in place as I opened my mouth.

On my other side, Jason didn't appear to be too upset that I wasn't beating him off anymore. Instead, he made the best of his situation by lifting up my left leg while my other leg rested on the couch cushions. Jason spread my legs, giving him a full view of my pussy, which was really starting to get wet now. Soon, it would be wetter than it had been in a long time, as excitement began to win out over nerves.

As I sucked on Leo's cock, I expected Jason to begin playing with my pussy. To my surprise, he actually started out by gripping my ankle and pulling my foot, still clad in the high heel, toward his mouth and began to delicately lick the tips of my toes. I remembered how Jason had admitted years ago that he had a fetish for my feet - just mine, he had said - and how wild it drove him to see me in the right high heels. It was another one of those things he had confided in me when he was really tired. I can't say I didn't have Jason in mind when I specifically chose these sexy shoes. I thought his fetish was really cute, actually, and his licking my feet was really sexy.

My head bobbed up and down Leo's cock while one of my hands held his stiff boner in place and the other now rubbed his balls. Leo ran his fingers through my hair, which came out from the Santa hat, while Jason's tongue brushed over each of my toes before sliding up to the top of that foot and tracing upward. He continued up, licking my ankle, then my shin up to my thigh, drawing closer and closer to my sweet center of sin.

The farther Jason's tongue came up my leg, the more I started to twitch and grow excited as I awaited what came next. All the while, though, I diligently blew off my other friend, who continued to play with my hair. Finally, Jason reached my pussy, sticking one finger on my clit while his tongue poked into my twat and began to lick me. I briefly pulled my head away from Leo, instead stroking his member furiously while I moaned and kicked my left leg straight up into the air.

My brain swirled with the sensations and excitement of my current situation. Never before had I been the object of obsession for two individuals at once. On one end, I was in control as I went back to sucking off my good friend, and, at the other end, another friend was eating me out, so that I was pleasuring and being pleasures at the same time. Focusing on blowing Leo was a little more difficult while I was receiving oral at the same time, but somehow I managed. It was like doing 69 only better because I had more range of motion.

After a few minutes, I was getting really worked up, and I'm sure the boys were too. I eventually shifted to my hands and knees, which forced Jason to pull away. Before he could get back in, I decided to switch sides, turning around so I was facing Jason's engorged cock. I spread my legs just enough so Leo could get in there and begin to fuck me with his finger while I went right to work sucking on Jason's cock.

Jason cursed and begged me to continue. The guy had waited a long time for me to blow him, so I happily looked up at him with my bright brown eyes just under the fluffy hem of my festive hat while my mouth slurped up and down his rigid cock. At the other end, Leo knelt behind me and put one hand on my bare ass while vigorously sliding his index finger in and out of my pussy, getting me nice and wet as we began to finalize preparations for the main course.

We fooled around on the couch for just a few more minutes until we were all incredibly horny and ready to get to the headlining event. I gave Jason one more drawn-out lick up the entire length of his cock, looking him in the eyes the whole way, before pulling away while Leo was still fingering me at the other end. I slowly pulled away from Leo, trying to stand up in a sexy manner and tried to showcase my ass for the guys as I got up and strutted back to the middle of the room. I started to direct again, and the boys eagerly complied. I think they were both so turned on at this point that they hardly noticed each other there or they were just eager to double-team me.