Sexploits Ch. 10: Jessica Pt. 02

No girl has impacted me like my friend Jessie, and no sexual experience has affected my life more than the one I shared with her on December 26, 2013. Yes, we did slip up earlier that year when I took her in during a snow storm. It wasn't our intention, but we ended up having sex that night, the result of nearly 10 years of unresolved sexual tension. By then, Jessie had been married for a little while, so we both knew it was wrong and swore to never let it happen again. We meant it too, so I figured my involvement with the hottest girl I'd ever met had peaked with that one regrettable event.

What neither one of us anticipated was that Brian, Jessie's husband would be one to share. Then came that fateful date, when the couple, who had moved away not long after Jessie and I slept together, was back home visiting family for the holidays. It was six months after Jessie had a baby, which, if nothing else did, seemed to rule out any possibility that we would stumble again. There wasn't possibly a scenario that would serve nothing better than ruining someone's life.

Still, Jessie and I remained best friends even after the incident, although things were kind of touch and go for a while. But it wasn't long until we were confiding in each other again, and soon thereafter, we were comfortable with sexual topics again. One such topic was a fantasy I had had for several years that Jessie wrestled out of me via text one night when I was very tired and not exercising my best judgment. Of course, I never would have imagined what the outcome of sharing that fantasy would be. Had I known, Jessie wouldn't have had to work nearly as hard to get my confession, and just maybe our ill-advised incident from earlier in the year would have never happened.

So there I was, the day after Christmas three and a half years ago, sitting in the living room of some strangers' house that Brian and Jessie were house-sitting. The baby was with Jessie's parents, so it really was the perfect setup for something this incredible to take place. With me in that living room was Brian, someone around whom I had never been totally comfortable, and that was before the past winter. I remember wondering if he had any idea I had slept with his wife. That guilt and shame plagued my conscience in that moment, but it wasn't the main reason I was nervous. The nerves were because of the excitement of knowing Jessie was in the bedroom down the hall getting herself ready to be the center of attention of two men. Fantasizing about it was one thing; anticipating the actual act came with a brand new set of feelings.

None of us had ever participated in group sex before and none of us had admitted to ever thinking about it until I did to Jessie that one night a couple months back. It was something I would have admitted to no one else but Jessie, and I'm still kind of shocked I did that much. To think that that moment of shameless honestly had me moments away from fulfilling my wildest fantasy! No other circumstances would have had me in this situation. It had to be two men, it had to be heterosexual, and it had to be Jessie.

At last, after what felt like an eternity of awkwardly waiting in the living room with the husband of the woman I had obsessed over for years, the door to the bedroom swung open, and out stepped just the right leg of my best friend, but it was enough to get me hard right away. Just the sight of that six-inch black high heel shoe, those pretty, pedicured toenails complete with red nail polish and nothing covering that sexy, slightly tanned leg was all I needed for my heart to go wild in my chest. It got only better from there.

Once the thin 5'5" babe was in full view, she took my breath away. I had never seen anything hotter in my life, and it was going to keep getting better. She was draped in a red knee-length robe with fluffy white trim and topped off with a Santa hat, all of which was a very sexy incorporation of the holidays. I was dying to see what was underneath. In addition, she wore the black heels and two bracelets - a silver one and a gold one - around her left ankle, and her fingernails matched the shade of red on her toenails.

Of course, Jessie could have been wearing a burlap sack and would have still had me ready to fuck her. For starters, her shoulder-length brown hair was slightly curled out as it hung down, perfectly done. Equally perfect was her makeup, just the right amount to brighten her face without being overdone. Her gorgeous deep brown eyes pierced to my soul, and, perhaps her sexiest asset, her flawless mouth, complete with bright white teeth and red lips, was curled in the most arresting and wicked smile I had ever seen. Some girls are so hot that they just beg for a cock. Then there are girls like Jessie who are so hot that one cock just isn't enough, and that's what this fantasy was all about.

My throat went dry as Jessie made her way to the living room where we boys sat. Her high heels clacked against the hardwood floor, the only sound in the otherwise silent house. I could tell Jessie was just as nervous as I, though she was hiding it pretty well. As soon as she set foot on the carpet in front of us, she pushed the robe off, her nerves be damned, revealing the sexiest lingerie I had ever seen.

Her Christmas-themed teddy certainly didn't detract from her knockout appearance, as she sported a red thong with fluffy white trim and a matching bra that covered barely half of her breasts, which, created more cleavage than I thought possible. Her boobs weren't huge, but the right size for her frame. The halves of the bra came together on her chest in a festive bow that begged to be undone. Her lightly tanned skin shone gloriously in the overhead lighting.

At this point, I forgot Brian was even there. All of my attention was glued on Jessie, who smiled somewhat anxiously while all of us must have been too nervous to make any type of move. Finally, Jessie suggested that we all take our clothes off. There was no need to draw it out, as we were all eager to get to the main event.

Jessie waited for Brian and I to stand up and begin to disrobe. I had never before stripped naked next to another man, especially while sporting wood, but it was surprisingly not all that uncomfortable for me. Like I said, I was so entranced by Jessie that I hardly noticed another man's presence. Beside, this was my fantasy, so I needed to deliver.

Once both Brian and I had undressed, Jessie followed suit by removing only her thong for now. I literally shivered as her hands pushed that small piece of cloth away from her hips and down those slender legs, eventually letting it fall around her ankles. Next, she stepped out of the thong and directed us to the couch, having us sit on either side of her. Brian took a seat on Jessie's right side, while I sat down on her left. With only her body separating us boys, Jessie took each of our cocks in her hand, stroking up and down, handling two cocks at once for the first time in her life.

Jessie increased her pace, beating both of us off faster as she grinned from ear to ear. I couldn't believe my best friend was giving me a handjob while her husband sat on just the other side of her! She didn't keep her hand on me for long, however, as Brian pulled her toward him, guiding her head toward her cock and forcing her soft hand away from my manhood. As she began to obediently suck her husband's cock, I wasn't upset that she was no longer paying attention to me. Instead, I took the opportunity to play with other parts of Jessie's unbelievably sexy body.

Jessie was now lying on her right side, blowing Brian, and I lifted her left leg, while the other leg remained on the couch cushion. I contemplated moving right in on the pretty pink pussy of hers, but what I really wanted to do, as odd as it may sound, was lick her feet. I had already told Jessie years ago that I thought her feet were sexy in the right shoes, and those open-toe heels she was wearing certainly qualified. Considering the circumstances, I figured now was my best chance to go for it, whether her husband was there or not.

I pulled Jessie's left foot up to my mouth and started by licking the tips of her perfect toes. I brushed my tongue back and forth a few times, giving each toe a dab before tracing up the top of her foot and slowly moving up to her ankle. All the while, my friend's head bobbed up and down as she polished Brian's knob, as if she were oblivious to what I was doing to her at the other end.

My mouth made it's way to Jessie's ankle, then up her leg and eventually to her thigh, inching closer and closer to my prize. Jessie continued to suck her husband expertly, but her body was twitching more and more as I made my way up her leg. Finally, I reached her glistening vagina and decided to rub her clit with one finger while continuing to taste my best friend's body.

The second I began to lick Jessie's pussy, Jessie slightly pulled away from Brian's cock and moaned loudly as she kicked her left leg straight up into the air, the bracelets clattering against each other as Jessie allowed me full access to her cunt. Her moan was so sexy that it encouraged me to just lap up her juices faster and more feverishly. Then Jessie took Brian's cock back in her mouth, her head bobbing up and down again, so that she was both giving and receiving simultaneously.

Eventually, Jessie got to her knees and straightened herself out, incidentally pulling away from me. Before I could get back at her sweet pussy, she turned around so that her head was by me instead. With those perfect eyes locked on mine, my pretty friend sucked my cock while the puff ball on her Santa hat swayed back and forth. Meanwhile, Brian had set up behind his wife and began to finger-fuck her while she blew another man.

I could hardly contain my moans as Jessie's pretty wet mouth slurped on my manhood. While her husband slid his finger in and out of her harder and faster, Jessie began to moan around my cock but continued uninterrupted. At last, after several more minutes of foreplay on the couch, Jessie lifted herself off the piece of furniture and strutted to the middle of the room, where the first helping of the main course would be served.

For now, the robe and thong remained the only clothing Jessie had discarded while she waited for Brian to join her on the floor. I got up too, of course, as I was eager for what was coming up, but Jessie intended to start off with her husband. Brian lay on his back in the floor, and Jessie knelt beside him, doing what she did so well and sucked his cock. I felt a mix of arousal and jealousy from seeing my best friend blow another man, though I had no right to be jealous, since that man was her husband and I was the lucky bastard with whom he was sharing his wife.

Next, Jessie mounted Brian, her back facing me as she looked down into her husband's eyes and put her hands on his chest. The same feelings of arousal and jealousy filled me as my gorgeous friend proceeded to ride her husband right in front of me. After a moment, Jessie turned her head back to me, those eyes peering just under the hem of that Santa hat and filling me to the brim with desire for her. As she still fucked her husband, she beckoned me over, inviting me to join.

First, as I stepped up to the couple, Jessie took me in her hand and beat me off as she continued to pump her sexy body up and down her husband's cock. I simply stood still and sighed with pleasure as I watched my hot friend stroke me while she rode her husband steadily. Her ass slapped against Brian's flesh as she went up and down again and again, all the while sliding her hand up and down my shaft and occasionally rubbing her thumb against my tip.

Next, Jessie leaned over and stuck my member back in her mouth. In order to focus on sucking me properly, Jessie desisted from riding Brian, who in turn grabbed his wife's hips and began to thrust up into her himself while Jessie slid her head back and forth on my dick, making me moan even louder. Taking her hand off my penis, Jessie reached around her back and finally removed her bra, freeing her boobs and allowing the garment to fall to the floor. Now all her best parts were exposed, and the remaining shoes, anklets and hat only enhanced her sex appeal.

Jessie's hair and boobs rocked up each time her husband slammed into her from underneath, but the lady's body stayed in place as she continued to blow me, her hand now back on my balls. At last, she pulled her head away from me, going back to stroking my cock fast and with determination, as those eyes gleamed devilishly at me while she uttered words that sent chills of excitement down my spine: "Fuck my ass!"

It was finally time to fulfill my most secret and depraved fantasy, one I had never shared with anyone until the night I shared it with Jessie. To me, there was nothing hotter than a sexy girl's getting double-penetrated, and no girl was sexier than Jessie. Now that she had been worked up plenty, she was ready to provide us the main course, which was a delicious Jessie sandwich.

Brian came to a stop beneath Jessie and helped lower her down so that her boobs were pressed against his chest. In the process, Jessie let go of me, and I saddled up behind her instead, my eyes fixed on the vacant dark hole that was my duty to fill. Just underneath her asshole was her pussy that was already stuffed by her husband, so there truly was nowhere else to go. Dropping to me knees while my heart seemed ready to burst, I guided my cock between those lovely ass cheeks and prepared to give Jessie the treatment she had always needed.

Up until then, I had never been inside a girl's ass before, so I wasn't sure what to expect. Jessie and Brian stayed still, and Jessie reached back to spread her butt for me as I pushed the tip of my cock against her dark hole. Once I began to wedge in, Jessie cooed, and I stopped breathing. It was a tight fit, not only because it was her ass but also because her neighboring pussy was already stuffed. Thankfully, having the other guy right there wasn't as unnerving as I had always imagined. I was far too excited to be double-fucking Jessie to let another ball sack knock me off my game.

Inch after inch of my manhood penetrated Jessie's ass, causing the girl to cry out louder and louder as she buried herself into her husband, who continued to hold her in place. I was already sweating a little as I pushed as hard as I could until, at last, I was all the way in. I felt like I was dreaming, and I certainly had had this dream before. It was real life this time; both Brian and I were actually balls-deep inside his wife!

I don't know how long we all silently stayed still. I'm sure it wasn't as long as it felt, but I know that I, at least, was somewhat in awe of what was happening. Before doing anything else, I just kept scanning up and down Jessie's incredible body, especially her stuffed holes and stretched-out taint. I swear I got even harder at that sight, as if that were possible.

Eventually, I began to pull back enough so that only the head of my cock was still inside Jessie. Then I slowly thrust forward and began to gently screw her ass in an effort to get this double-penetration threesome going. Brian followed right behind me, he too sliding very slowly back and forth inside his wife while I did the same in her ass. In response to the double-fucking, Jessie cursed loudly and sank her nails into her husband's chest before pushing herself up in order to angle herself just right, halfway between us two men as we slowly worked up to a shared faster pace. Still moaning, perhaps from pleasure but probably pain, Jessie kicked her left leg back, her knee remaining on the carpet as the heel of her shoe pointed to the ceiling. I continued to hold tightly to her hips while Brian had a firm grip on her shoulders, holding the sexy woman in place between us as we adjusted to this brand new position.

Just as I felt I was ready to really pummel Jessie's ass, Jessie began to rock her body back and forth, doing the fucking instead while Brian and I responded by staying still. In just a minute, Jessie was humping both our cocks in unison at a surprisingly fast pace. The young lady actually laughed a little, amused if nothing else, as she fucked two cocks at the same time, taking us both to the hilt inside her holes. My mind didn't even know what to think as it swam with all the sensations of this truly unreal experience.

Jessie kept going faster, to the point that her Santa hat finally fell off, allowing her gorgeous hair to shift about as she rocked herself back and forth, being penetrated deep in both her ass and pussy each time she slid backward. I could see that she was already sweating, and her breathing had become ragged as she rode those two cocks with determination. All the while, she switched her gaze back and forth between us two boys, those endearing eyes and that wicked smile both melting my heart and driving it wild with lust as she fucked Brian and me with remarkable stamina.

As admirably as she was performing, Jessie eventually slowed to a stop, as it appeared the discomfort had become too much for her. She whined as she lowered herself down, lying on top of her husband as he and I remained stuffed fully inside her. As the brunette beauty caught her breath, though, my lust would not allow her to stay at rest for very long.

I got it started again by slowly sliding in and out of Jessie's ass, and Brian followed right behind me by pushing up into his wife's cunt. However, we only began to increase our pace when Jessie requested a change of position. My initial reaction was worry that Jessie was too uncomfortable and that this endeavor was going to be a failure, but, at the same time, I was eager to try a different position.

I pulled out first, and Jessie hopped off her husband. As she got to her feet, she stumbled a bit, her high heels not helping the fact that both her holes had just been stiffly fucked. Once she gained her balance, Jessie made her way to the couch, looking sexy as hell in only her shoes and those bracelets around her left ankle. Again, Brian took his position first, sitting down on the couch as Jessie turned, facing away from Brian, who took hold of his wife's waist and guided her down toward his still-erect cock.

Brian and Jessie both took hold of Brian's cock, and Jessie lowered herself slowly to accept the prick gently into her ass while her feet were planted on the floor. In a moment, she was sitting in her husband's lap, her ass stuffed with cock. Next, with her hands supporting her on the couch, Jessie grinned sinisterly at me and lifted her left leg straight into the air, spreading her pussy and inviting me in. She looked so hot in that position that I swear I almost fainted.

I hurried over to the couple on the couch and quickly stepped over Jessie's right leg, wedging her thigh between mine and Brian's. Then, as Jessie held herself up with her arms spread out on the head cushions of the couch and her left ankle resting on my shoulder, she and I looked on with indescribable excitement as I pushed my phallus against her tight opening and began to sink in.

It was a tight fit, thanks to Brian's cock on the other side of the membrane that separated Jessie's ass and pussy, which made the sensations all the more incredible. Jessie and I moaned in unison as I sank deeper and deeper into her until my balls joined Brian's sack on Jessie's taint, the bitch now double-stuffed once again, only this time in the hottest position imaginable in my opinion. Words fail to describe the reality of my experience in that moment.

The following moment was filled with heavy breathing and groaning as we all took a minute to adjust to our position. With a little shifting of our bodies, we soon had Jessie comfortably sandwiched between the two of us boys, who were ready to give her the stiff double-fucking her sexiness required. With Brian's hands on Jessie's waist, I wrapped one arm around the leg that had been on my shoulder and put my other hand on Jessie's right arm, which was outstretched along the couch. We were all set to go.