A Delicious Jessie Sandwich

The shot glass shook in my hand as I endured the most awkward 10 minutes of my life. I've never been a drinker, but the alcohol was needed tonight to calm my nerves as I sat across the glass coffee table from the husband of the girl whom we were both about to fuck. I wasn't going to get drunk, but a bit of a buzz would help push me over the edge into this act of decadence.

This other man and I sat in his friend's living room, waiting to begin something none of us had ever tried before. I wasn't too well acquainted with the man across from me, but Jessie, his wife, had been a good friend of mine for nearly 10 years. She and I had had an up-and-down relationship that flirted toward romance a couple times before she got hitched. On top of her fun, daredevil personality, it didn't hurt that she was a fit, 5'5" hottie with slightly tanned skin, straight, shoulder-length dark brown hair, firm boobs, a hot set of hips and sexy legs.

A few years ago, not long after their wedding, the couple moved away and, shortly thereafter, had a baby. Over the years, my desire to plug Jessie never abated, but my hope certainly did as we approached our late 20s. That fortune all changed around a year ago when Jessie and her new family were visiting during the week of Christmas.

There I was, the day after Christmas, anxiously waiting for Jessie as she prepared in the bedroom. As fate would have it, one of her friends was taking a vacation for the holidays and had let Jessie's family house-sit for her. Now we didn't have to contend with roommates, parents or neighbors in an apartment complex or hotel. In addition, the baby would be spending the night with Jessie's parents.

The wheels had been in motion for the most memorable night of my life for the past several weeks, if not months. Completely independent from me, Jessie had been formulating a plan to include me in a hot evening of dirty sex. I was excited at the prospect of finally being able to fuck one of my best friends, even if it was adultery. However, the offer came with a deal-breaking catch.

I tried to keep the shot glass from vibrating in my hand, but the only thing I could do to not draw attention to my nerves was take another drink. Finally, what little conversation had ensued between us two men quickly ended once we heard the bedroom door creak. Immediately, we both looked over to the opening door, where Jessie's leg slipped out just before the door swung open, putting Jessie, the sole attraction, in full view.

Jessie clearly had a case of the holiday spirit, as her body was covered in a knee-length red robe with fluffy white trim to go with a matching Santa hat upon her head. I knew in a few moments that all of her festive clothing would be taken clean off of her, but for now, her incorporation of the holidays into our rendezvous was a sexy touch.

The only other attire visible were two bracelets - one gold, one silver - around her left ankle and her six-inch black high heels, from which protruded her red polished, pedicured toenails that matched her manicured fingernails. Her heels clacked on the hardwood floor as she started to make her way toward us boys. Her grin was seductive and eager but it also betrayed her nerves as she strutted to her fate.

It had been revealed to me that the couple had been toying around with the idea of a threesome for some time, and Jessie had convinced her husband to allow me to participate. As Jessie approached us, it was very apparent that neither she nor I had experienced a devil's threesome before. I could only assume her husband hadn't either. Regardless, our lack of experience did not taper our enthusiasm.

My feelings for what was about to transpire were mixed, naturally. While Jessie's being nailed by two guys at once would be as hot as hell itself, being in such close proximity to another guy - not to mention Jessie's husband - during sexual intercourse was at the very least unnerving for a heterosexual man. Those qualms paradoxically both waned and heightened as the object of my obsession drew nearer to me.

As soon as Jessie set foot on the carpet of the living room, she pushed off her robe to reveal matching Christmas lingerie. The halves of the bra, trimmed in fluffy white, met diagonally in the middle of her chest where they tied together in a festive bow, revealing more cleavage than I thought she had. Beside the hat, bra and heels, she wore a bright red thong with matching white trim along the top.

Never more aroused in my life already, I was pitching a tent in my pants before Jessie's robe hit the floor. Since Jessie's husband wasn't making a move, I awaited Jessie's cues as to what to do. Visibly anxious, Jessie suggested we all take our clothes off.

I did my best to ignore Jessie's husband's presence as I disrobed, and it surprised me how easy it was, actually. My eyes were glued to Jessie even before she started to push her thong down her hips and thighs, making me completely oblivious to her husband who was practically right next to me. As I continued to strip down, Jessie let her thong fall to her ankles before she kicked it disdainfully aside, leaving all of her holes exposed.

Things heated up quickly after Jessie removed her thong, exposing her ass and pussy to me for the first time. Soon, her husband and I were naked, our cocks free at full mast, and Jessie was giving orders, looking very sexy while still wearing the hat, jewelry, heels and bra. I could barely take in how hot she was in that moment, having really no idea yet what I was in for.

We wasted no time, getting right to it as Jessie's husband obediently lay on the ground, his erection poking straight up. For the next couple minutes, Jessie ignored me as she knelt down beside her husband and stroked his cock before leaning forward and putting it in her mouth. It felt a little uneasy at first to watch my friend suck off some other dude, even if it was her husband. However, I paid my attention to Jessie, to her pretty mouth sucking the length of that dick and her hat and hair's bouncing around as she did so. I quickly learned that focusing on Jessie made it much easier to become aroused rather than uncomfortable.

Once she had her husband's cock nice and lubricated with her spit, Jessie stepped up and prepared to mount him. In that moment, I felt a bit of jealousy rise, but that feeling faded quickly. As her husband's cock poked her vagina, Jessie lowered herself onto her husband's cock until she slid down to the very base as she leaned forward and propped herself up on her husband's chest.

Jessie's husband groaned as Jessie rotated her hips, grinding him briefly, leaving me to just watch. Then she lifted herself up, only to drop back down before doing the same thing again and then again, only more quickly. It was a little awkward but really hot also to see my good friend in her sexy Christmas outfit as she bounced up and down a stiff, hard cock, her knees on the carpet on either side of her husband's hips. Her husband held onto her thighs and thrust up into her, going balls deep as they fucked right in front of me.

Turning her head to face me, Jessie smiled devilishly and looked up at me with those piercing brown eyes just below the hem of the Santa hat. She seductively beckoned me over with her finger while she grinned wickedly from ear to ear. I almost forgot to breathe as I stepped forward, making my way to the couple that was already in the throes of intercourse.

Involving any other woman or with any other circumstances, I almost certainly would have not participated in this activity. However, I knew passing off this opportunity to someone else would haunt me for the rest of my life. As Jessie reached up to stroke my cock as she rode her husband faster and faster, I was committed. Her contact with my dick finally marked my first real sexual experience with the girl of my obsession.

She slid her soft hand up and down my shaft slowly at first, occasionally rubbing the tip with her thumb, making me moan. As she adjusted to beating me off, Jessie stopped riding her husband and let him hold her in place and fuck her instead. Then she shifted toward me and took my cock into her mouth.

The second Jessie's wet tongue touched my cock, I moaned loudly and put my hands on Jessie's head. I pushed forward gently to fit as much of my dick into her oral cavity as possible, and she started to suck me off. As she licked my shaft, Jessie reached down to undo the bow on the front of her bra, allowing it to fall off her body as she took a cock in either end of her. Now revealed, her perky boobs shook with her body and hair, the puff ball at the end of the hat swinging around wildly amid the intercourse as her husband thrust repeatedly into her pussy while I enjoyed a blowjob at the other end. I could hear Jessie's body slap against her husband's as she took the base of my cock back in her hand and started to slurp on my cock. She looked good with a pair of cocks in her, and the main course was going to look even better.

Jessie's lips and tongue played with my cock for several minutes, preparing me for the real fun as I started to clench my hands, pulling on her hair. After sucking the entire length for a little while, she focused on the head and tip, flicking her tongue against it and licking it gently. Then she went back to stroking and sucking me off, as all the while her husband was slamming into her from underneath.

Finally, Jessie pulled her head back from my cock with a gasp but continued to stroke it as she went back to grinding on her husband. Those piercing eyes met mine again as her beautiful mouth uttered the last words I'd hear before the real pleasure began: "Fuck my ass!"

What had sold me on this opportunity was Jessie's specific mention of the fact that double penetration was something she had wanted to try since her college days. To be completely honest, sandwiching Jessie was something I had always wanted to at least watch, if not do, though I previously would have never admitted it to anyone. That kind of thought was something I'd often fantasized about for years. In my mind, nothing was hotter than the thought of Jessie's sexy little body sandwiched between two dudes who were filling her holes and stretching out her taint.

With Jessie's words, nothing stood in my way. I knew better than to over-think the situation. I needed to just do it. Jessie and her husband came to a stop from their fucking as I stepped behind Jessie. Her pussy was completely filled with her husband's cock, but she helped me find the alternate entrance by lying down on her husband and spreading her ass cheeks nice and wide with her hands. I squatted down behind her, my gaze transfixed on the vacant dark hole.

My mouth went dry as my breathing fluctuated. Meanwhile, my heart pounded anxiously in my chest. I was still completely turned on, though, and with my rock-hard cock in my hand, I leaned forward some more, aiming for that tight asshole that would forever etch this night into my memory.

Jessie was breathing faster too while she held her ass open and her husband pressed her in place against himself. I was just moments away from fulfilling my dirtiest fantasy and, even though the time elapsed was probably about 10 seconds, it felt like another five minutes before the head of my cock poked Jessie's ass, guided by my hand. Jessie whined quietly when my tip made contact with her flesh. I swear I could feel my cock get even harder as I continued to look steadfastly at my lover, whose twat was filled to the hilt with another cock already while I attempted to fill the neighboring hole simultaneously. I pushed forward just enough to wedge the head of my cock into her before releasing my cock and taking another deep breath.

Her eyes wincing shut, Jessie cooed as I thrust forward slowly, entering her asshole inch by inch. I had to grab the base of my dick a couple times to help push it in, but there wasn't too much resistance despite her tightness. Her breathing became more ragged, and her red nails dug into her husband's shoulders as more and more of me filled her. I could feel the hard cock on the other side of the membrane that separated Jessie's ass and pussy. The feeling was weird and incredible at the same time. The pressure added by the other cock was only enhancing the experience of plugging Jessie's asshole.

Again, actual time and my perception of it weren't matching up. That first thrust into Jessie probably took only a few seconds, but it felt like much longer as I took it all in. I slowly exhaled a few times, balancing myself on her ass with one hand as I sank deeper and deeper into her until, at last, my balls rested on Jessie's taint and my body made contact with her ass. Jessie cried out either in pleasure or pain; I couldn't tell. I put my hands on Jessie's hips and held onto her as my cock adjusted to the pressure inside her. It was a tight fit, but the sensations were amazing even before reality sank in.

I had been entranced with Jessie's asshole, but now that I was to the hilt inside her, I looked up to see that Jessie was looking back at me. I could see just the corner of her mouth over her shoulder as she grinned, clearly madly amused, but those beautiful brown eyes really caught my attention as I gazed back at my beloved, naked friend. It was at that moment that my situation finally took hold of me.

The past few minutes had seemed to be in slow motion, but upon making eye contact with Jessie, it was as if the play button had been pressed to return us to live action. I looked away from Jessie's face and looked down to see again that I was balls-deep in her asshole. I leaned over to check out her stretched-out taint and stuffed pussy, a sight that drove me wild with unquenchable lust. Not only was I inside Jessie, but she was stuffed in both holes! Her tight pussy and asshole filled to capacity raised the bar for the hottest thing I'd ever seen, and the sights and sounds were going to get only hotter as the activity progressed. Meanwhile, Jessie looked beyond pleased to finally be filled by two guys at once.

Up until this point, not one of us had either moved or spoken. The only sound was our heavy breathing and a couple giggles from Jessie as we all adjusted to the pressure and prepared for one hell of a fucking, which this girl needed. Leading up to this moment, I had worried how I would perform with another guy involved, but I had underestimated Jessie's sexiness. Having her body as the meat in this sandwich made me wholly willing in that moment of time to give myself over to this sinful act of depravity.

With renewed gusto, I inched my cock back until only the head was still inside Jessie's ass. Jessie moaned softly as the veins of my cock slid against her insides. Then I pushed forward, steadily sinking my whole length back into her, which caused a gasp and a louder moan from the girl as she lowered her head and again sank her nails into her husband. I held onto her more tightly and began to fuck her ass just as her husband began to stir underneath her.

Jessie cursed and then planted her hands on the carpet on either side of her husband, holding her body up halfway between the two of us as we only began to double-penetrate her. I held myself up by her hips as I hovered over her ass, leaning over her and sinking my cock into her asshole a few more times before getting the hang of it. Meanwhile, her husband had started to steadily thrust in and out of Jessie's pussy as Jessie tensed up, threw her head back and moaned. Her hair brushed my shoulder as she jerked back, and she kicked her left leg back up into the air, her knee still against the carpet as she flexed her ankle. The heel of her shoe pointed up at the ceiling as the anklets rattled slightly. Her jerking movements caused the Santa hat to sit on her head crookedly. For now, though, it remained on as her husband and I looked to establish a rhythm.

Before we guys could really get going, Jessie grew more comfortable with her predicament and started to fuck us instead. She lowered her leg back to the ground and started slowly rocking her body back and forth on our cocks but quickly grew more eager and slammed back into us hard and fast. I continued to support myself on her hips while her husband held onto her shoulders as she slid up and down the full length of our cocks. My balls continuously slapped against her taint as I stayed still and let her polish my knob with her shitter. She cried out with sounds of both joy and agony as she took us deep into both her holes.

I held my breath as I watched Jessie fuck us. Her Santa hat finally fell off, leaving her clad in only her high heels and anklets as her body thrust back and forth, being penetrated in both her ass and pussy simultaneously. The bitch rocked her body with remarkable stamina for a couple minutes, moaning and panting as she did.

Jessie couldn't keep up the fucking, though, and, after a while, I think the discomfort became too much for her. She slowed down, gasping for breath and whining a little as she sank down onto her husband after doing an otherwise terrific job of pleasuring two men at once. I took this opportunity to begin fucking her ass again, thrusting in and out of her steadily while her husband grinded up into her other hole.

Before her husband or I could really get going, Jessie requested that we get on the couch and change up our position. I was anxious that she wasn't enjoying herself, but neither one of us guys was going to argue over positions, so we did as she wished. The experience was hot and wild on the sole fact that Jessie was getting nailed like a whore, but it hadn't quite reached that next level. However, the formation Jessie was looking to try next was straight out of the fantasy that had played over and over again in my head for several years.

Once Jessie gave the next instruction, I pulled out of her ass with new excitement, eager to take Jessie from another position. Jessie stood up and directed her husband to sit down on the couch. Then, Jessie sat down on him, her feet on the floor, her body facing away from him. She first positioned her ass over his cock, and using her hand and his, pushed the cock into her shitter and slowly sank down until she was sitting on his balls. The couple stayed still as Jessie summoned me over, that wicked grin magnetizing me to her.

As I stepped up, she lifted her left leg straight into the air, inviting me in. Enjoying the incredibly hot view, I stepped over her right leg, and she rested the other leg on my shoulder, her anklets rattling with the movement of her leg. Just the contact of her leg on my flesh made me shudder with excitement as I guided my cock toward her pussy with my hand. She was so close to me that I could feel the heat emanating from her body.

Finally having Jessie's twat would be the culmination of years of sexual frustration. The fact that she was being double-penetrated was just icing on the cake. Holding herself up with her right arm, Jessie reached up and clutched my back with her other arm, allowing me to shove the head of my cock inside her, neighboring her husband's cock that was already deep in her asshole. At first I tried to avoid contact with her husband, but that distraction was already causing me to lose wood, so I stopped worrying about it and focused on the girl.

Jessie's pussy was so wet that my cock slid effortlessly inside her, despite her tightness and even with her asshole stuffed. I could feel the hard dick on the other side of the membrane, but I had let go of those qualms and actually welcomed them now. Within seconds, I was balls-deep in Jessie's cunt as my body slid up against hers, coming together like two puzzle pieces. Her body was already slick with sweat from our previous endeavor.

I couldn't contain my moan of pleasure as I took in the fact that I was inside Jessie's twat. Being pressed up against her made the experience all the more intense, as Jessie's head was up against mine, her mouth at my ear, her boobs pressed against my chest while I ground up on her. The sound of her heavy breathing filled my ear, joining the sound of my own. The heat from her body was already making me sweat while my heart pounded so hard that it almost hurt. Jessie sank her nails into my back and her leg slipped down onto my arm as she adjusted once again to being double-stuffed.