A Delicious Jessie Sandwich free porn video

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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 d****d 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.


Now we can fuck her!" Brian announced. It was the only cue I needed as I pulled back on top of Jessie and thrust back into her. Right behind me, Brian began to fuck Jessie's ass, causing the girl to squirm between us as we began to double-dick her. Jessie immediately began to moan, her mouth right against my ear as I leaned over her right shoulder while Brian was below her other shoulder. The heat emanating from Jessie's body had me sweating again already as we only begun to fuck her on that couch.

As much as I loved the feel of Jessie's boobs pressed against my chest, I couldn't help but back off occasionally to admire the sex sandwich we had created. I gazed on in disbelief at those pretty eyes and gorgeous lips, down to her heaving breasts and, most of all, those two stiff cocks pushing in and pulling out of both her holes. I almost went dizzy with the realization that I was actually sandwiching my best and hottest friend, just like I had hopelessly fantasized for years. Nothing was sexier than watching this goddess take two hard cocks in both her holes.

Jessie threw her right arm around me, sinking her nails into my back as I lay back against her and established a rhythm with her husband, sawing in and out of her. Brian and I were essentially taking turns inside his wife, where I would pull out just as Brian sank in and vice versa. Throughout the whole thing, Jessie seemed to be genuinely enjoying herself, as she giggled and squealed as her body writhed between us, rocking as we thrust in and out of her. Her sexy legs thrashed out, causing the bracelets on her ankle to rattle, adding to the sound of pleasured moans, slapping flesh and the creaking couch beneath us.

As much as Jessie seemed to be enjoying herself, there was no way it was more than I was. The sounds, the sights, the sensations, the emotions, even the heat were all more than I was prepared to take in. Once we were in full swing, the threesome was incredibly hot and a ton of fun, all three of us having the time of our lives and Brian and I pumped in and out of Jessie like pistons in a well-oiled machine. At last, Jessie peaked first, screaming as she came, evidenced by her pussy's tightening around me, the heel of her shoe poking into my side and her nails clawing deep into my back. She even bit down on my ear a little as Brian and I fucked her right through her orgasm.

We both pumped back and forth into the same bitch, sawing in and out of her. I could hear her husband grunting beneath her and realized I was groaning myself as Jessie writhed and squealed between us, occasionally laughing as her head and legs swung between two thrusting bodies. I could feel the pointed heel of her right shoe poking my back rather consistently as she reacted to being pressed between and stuffed by the two of us men. At last, it seemed like Jessie was sincerely enjoying her situation. Her one arm still supported her on the couch, but the other hand was clawing and clutching at my back while her legs thrashed about as much as they were able while I sank into her over and over and over again.

I remember distinctly how hot the room became. I briefly pulled back to admire Jessie again and saw beads of sweat on her forehead and between her boobs. It felt like time slowed down again as I viewed her body, the entirety of which gleamed in the dim light from the perspiration. Her sweat-soaked hair was matted against her neck and shoulders and hanging down into husband's face, her arms bracing herself as she took the double penetration. Our eyes met once again during this moment, and I admired her pretty mouth, which hung wide open as she reveled in being the meat in our sandwich. Her breasts heaved as low, pleasured moans escaped from her throat, joining a myriad of other sounds, including the creaking of the couch beneath us as it supported us during this raunchy activity.

That moment of slow motion passed quickly though, and her husband and I kept up our pace as we pushed in and pulled out of Jessie faster and faster. At this point, joining the sounds of our moaning was the squelching of her wet pussy and ravished asshole. I also heard the wild rattling of her ankle bracelets against my arm, as her leg bounced in rhythm with our fucking. The smell of sweat mixed with Jessie's perfume became almost overwhelming as it joined with the sights and sounds of our group sex.

Forcing my cock as deep into Jessie's pussy as I could with each thrust, I focused hard to continue my rhythm with her husband, who pushed even deeper into her ass, separated from my cock in her pussy by only the thin membrane. The two of us held her still and tightly between our bodies so that the sweaty, gasping bitch lay there, getting double-penetrated and crying out with blissful agony with each thrust into her as her legs thrashed in the air, pinned within a mass of human flesh.

I never felt more alive in my whole life. The incredible sensations of feeling my cock slide beside another inside this hot woman would soon be more than I could take. We boys grunted harder and harder while Jessie was practically screaming at this point. Turned on only more, we sawed in and out of the writhing, sweating, moaning brunette between us harder and faster, rocking her entire body as she was helplessly caught in this hot, wet, delicious sandwich.

We continued to fuck her in unison on that couch, which now was probably on the verge of breaking and would probably be stained with sweat, as the temperature must have exceeded 90 degrees. We could only hope the family that lived here wouldn't notice any damage. Of course, in that moment, I don't think anyone could have cared less. We were having the time of our lives.

If not for the circumstances, the heat would have been unbearable for me as sweat leaked out over my entire body. I was even slipping against Jessie's damp body occasionally, but I would quickly straighten myself out and go right back to hammering her pussy and doing my part in this threesome. Jessie's body, of course, was slick with sweat from all three of us, but she had always enjoyed the heat, so it suited her all the better. She continued to cry out as she clutched the couch and my back while her legs bounced wildly on either side of me, her anklets rattling crazily and, for some reason, turning me on only more. If she hadn't been enjoying the double penetration before, she most certainly was now. I know I sure as hell was. I never wanted it to end.

The threesome continued for several more minutes as the sounds of slapping damp flesh, squelching holes, rattling jewelry and creaking furniture joined our cries and moans of intense pleasure to fill the room. We continued until I could hold out no longer. "Let's cum on her face!" I shouted with newfound confidence. No fantasy I had of double-penetrating Jessie was complete without giving her a double facial, so I wasn't going to take any chance of missing the cherry on top now that I was fulfilling that fantasy. We all quickly disassembled and got off the couch, Jessie suddenly vacant after having had both her holes stuffed to capacity. The girl dropped to her knees on the floor, and Brian and I stood up on either side of her, jerking ourselves off as we pointed out dicks at Jessie's grinning face.

Jessie closed her eyes and her mouth as she awaited her reward for which she had worked hard. I moaned loudly as my cock finally erupted, blasting Jessie in the cheek first and then unloading all over her pretty face. As if the experience wasn't close enough to perfect, Jessie's husband began to cum just a second or two after I did. He too was aimed at that beautiful grinning face. Her husband and I were soon painting Jessie's face in unison, in the same manner that we had fucked her body.

Time seemed to slow down again. I looked down with utter satisfaction as cum shot from both our cocks simultaneously and splattered all over Jessie. My cumshot covered her cheek and chin first, while her husband splashed onto her chin, nose, eyelid and other cheek. Still cumming, I moved my aim to blast her other eyelid and then her forehead, while my counterpart continued to plaster the side of her face and then moved down to her neck. A couple of my errant shots went into her hair. By the time we were finished cumming on her, we had covered her whole face while leaving some residue in her hair, and still more jizz was dripping down her neck down to her boobs.

As soon as I was satisfied, I exhaled heavily and collapsed in the easy chair behind me, while Jessie's husband headed off to the bathroom, I think, probably to clean up. As I took a minute to catch my breath and cool off, I sat in utter disbelief at what had just transpired and admired yet another hot sight I had helped create tonight as Jessie slowly stood up and wiped the cum from her eyelids, grinning from ear to ear as she did. As she strutted over to me drenched in jizz and sweat while dressed in only her high heels, jewelry and a smile, she assured me that tonight was everything she had hoped it would be and that we would be doing this very same thing again.

As I admired my sufficiently fucked, cum-covered friend that night, I couldn't know how my life had changed. Had it not been for Jessie's willingness to live up to my fantasy, my sex life would have looked much different over the course of the next few years. Since then, I had the confidence that led to incredible experiences with other women, including multiple gangbangs with a young lady friend of mine, two threesomes with a mature woman who had once been my boss at work and even one incredible night where I fucked two sisters back-to-back. Even out of all that debauchery, though, my first threesome with Jessie sits atop my most enjoyable experiences.

That first episode with Jessie was everything I had hoped it would be. I wished so badly that Jessie had never moved away. Maybe then it wouldn't have been more than a year before Brian and I double-penetrated her again, this time in a motel. About six months after that, I took the initiative to drive down to their place to join them for some raunchy fun. We double-fucked her twice that weekend, which was the first time she took double-vaginal penetration, a big step for all of us.

Then there were both Thanksgiving and Christmas of that same year that the couple was in town and made time for some more ungodly group sex. After that, it wasn't until July that they were back in the area, and we met up in a motel again for an especially hot session. That was the week we borrowed my uncle's boat and attempted to have a threesome in the middle of the lake. While Brian and I did manage to give Jessie double penetration out there, Jessie got really nervous, and the weather conditions were too difficult for us boys to actually fuck her properly. Otherwise it would have been a fantastic story to tell.

It was easy to forget that Jessie was a wife and mother through all this debauched shit. We knew it couldn't last forever, nor should it have, especially since the couple had a c***d. After nearly a year since that last attempt on the lake of not even seeing each other, I kind of figured our dynamic had run its course. The topic didn't really come up, and we all seemed to just go back to our normal lives.

It turns out we had at least one more session in us. In the past spring, I was confiding some personal issues with Jessie, who, in an effort to boost my spirits, suggested she and Brian come pay me a visit. I thought for sure she was joking, especially since we hadn't even referenced our sexual history in months. But before I knew it, she was asking me what weekend was good for me!

This time, I had my own apartment, so I could host. I suggested they just spend the weekend at my place, but they decided to stay some 40 minutes away at Jessie's parents' house to avoid suspicion. It was also free daycare, which I had forgotten to consider. Depraved sex wasn't going to work if a toddler was around.

Saturday night, however, Jessie's alibi to her family was she and her husband would be spending the night at a friend's place. It was the truth, actually, just not the whole truth. The couple showed up right at 8 pm. Jessie looked as good as ever, even if she had put on a pound or two since our first devil's threesome. It was warm out, so she wore cut-off Jean shorts and a brown sleeveless tank top, both of which were pretty ordinary, but she also added brown high heels, open-toe, of course, just for me, I'm sure. Her nails were a light pink, both on her toes and fingers. Her hair hung loose around her head, a little shorter than the last time I saw her almost a year ago and having a distinct red tint this time. Of course, her eyes and mouth were as pretty as always.

We caught up in the living room for a bit, but it wasn't long before the sexual tension mounted and led us to the bedroom. Within a couple minutes we were all naked, except that Jessie left the heels on per Brian's and my request. Brian then lay out his hot wife on my bed, ready to share her one more time. Again, I wondered if he still didn't know about the times I had had sex with his wife without him. Yes, by now it was times, plural. I just couldn't help myself around Jessie.

We boys took a few minutes to warm Jessie up, like we always did. I started with her toes and worked my way up to her pussy, while Brian started with her mouth and moved down to her breasts. In no time, my best female friend was writhing on my queen-sized bed and begging to have both of our cocks.

I got on my back, and Jessie got on top of me, taking my dick into her pussy. She ground on me for just a bit, her boobs and hair hanging down toward me. Then Brian slipped in behind her and impaled her ass, so that Jessie was stuffed in both holes for the first time in too long. As Jessie held herself up between us and moaned, Brian and I began to slowly slide in and out of his wife.

Even though it had been a while, it was close to the tenth time we had done double penetration, so Brian and I were able to pretty quickly work together and alternate thrusts into Jessie. Pretty soon we were sawing in and out of her hard and fast, our flesh slapping against hers steadily and consistently while she laughed and moaned between us. Jessie held herself up the whole time we fucked her in that position, which we did for several minutes until she came. Once Jessie's orgasm subsided, we all decided to flip the sandwich over and finish off that way.

We boys elected to stay with our respective holes to save time and effort with hygiene. Our setup worked well for us, since Brian loved screwing his wife's ass, which I think she let him do only in double penetration. I, on the other hand, could stuff that pussy all day long. Anyway, now Brian was on his back in Jessie's ass, while Jessie kicked her sexy legs straight up in the air, her heels pointing to the ceiling as I lay down between them on top of Jessie's breasts, sandwiching the bitch as I slipped my cock into her constricted pussy.

Brian and I went right back to it, fucking both of Jessie's holes hard and fast as we all bounced on the creaking mattress. All of us were moaning, but no one louder than Jessie, who clutched the sheets beneath Brian with one hand and my back with the other. Her legs alternated between wrapping around my waist and kicking up in the air as her body writhed between two thrusting male frames. Her high heels scratched my back, but I didn't care. Our sweat mixed and mingled as the room filled with the scent and heat of three bodies in the throes of intercourse, the sound of Jessie's squelching holes now joining the myriad of other sexy noises that overtook my ears.

At last, I could hold off no longer. I pulled out, and Jessie, reading my mind, said, "You want to cum on my face, don't you?" that wicked grin plastered across her face. I smiled and nodded, never imagining during the first near-decade of my friendship with Jessie that I would ever hear her say something like that. By now, Brian had pulled his wife off him and laid her on her back on the bed. I kneeled beside her head, and Brian beside her chest, opting to cream her tits while I blasted her face.

Brian unloaded first this time, I watching on as his cum splattered across Jessie's boobs. Seeing Jessie take a load of cum on her tits was the last thing I could handle. I moaned loudly as my cock exploded, unleashing a sizeable load on Jessie's nose, lips, chin and cheeks. As I finished, Jessie grinned, which allowed some of my semen to seep into her pretty mouth. I had successfully avoided her eyes, so she was able to open them and look back and forth between Brian and me as she continued to smile following being satisfied by two men like the sexy bitch she was.

Jessie, her hair and makeup a wild mess, kicked off her shoes and got up to clean up and get dressed as cum streamed down her face and tits. It was definitely a good look for her, one I had thought I would never see again. As her add swayed back and forth away from me, already all I could think about was when I could have another taste of that irresistibly delicious Jessie sandwich.

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1 year ago
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4 years ago
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2 years ago
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3 years ago
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Watching Jessie part 7

Watching Jessie It was Wednesday before lunch time when Terry. Who was Frank my bosses wife walked into my office and shut the door. She was a hot sexy black woman. I stood up from my desk as she said “hi sugar". I couldn’t help but stare at her in her short tight red dress. Terry knew that I liked looking at her. Terry started to tease me for spending Saturday night with her husband instead of her. I responded by saying that I would have much rather been with her but I didn’t think Frank would...

2 years ago
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The Softening of Jessie Part 7

Jessie sat on his bed looking at the new underwear his mom had bought him. Something wasn't quite right about it but he didn't know what. His mom was so supportive and understanding of his sensitive chest and his sudden weight gain in his lower section. He should be grateful that he has such a wonderful family. "What the heck. Let's try these bad boys on and see if they fit." Jessie stripped down and looked at the selection of underwear in front of him. The logical choice, he...

3 years ago
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The Softening of Jessie Part 22

Jessie grabbed the phone and gave Ashley a call. "What's up Ashley?" "Hey, I wanted to see if I could spend the night at your house. Jason is having some of his friends over and I don't want to be here with those boys." "Jason invited friends over for the night and didn't include me huh?" Jessie replied. He knew that his friendship with Jason was strained but it still hurt to be not included. "Yeah...sorry, but I'll hang out with you tonight. I promise I don't snore. Besides we...

2 years ago
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3 years ago
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2 years ago
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The Softening of Jessie Part 16

"What are you thinking Ashley?" Jessie asked. He knew she was always full of great ideas. "Well, seeing that you enjoy wearing your pantyhose so much, why don't we just buy you some shorts? Then you can keep your nylons on?" Ashley plainly stated. She knew it would not be hard to convince her feminine friend to take this leap. "I don't know. Are you sure you that people won't be able to tell I'm wearing pantyhose? I don't want to take the risk and look like a sissy, cause boys...

2 years ago
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The Softening of Jessie Part 35

The two headed over to the miniature putting course. Jessie was so happy with how the day was going so far. He was befuddled as to why he could not remember how throw a baseball, but the fact that Jason seemed to genuinely like him again more than made up for that. It was just like the old days again and he was hoping it would stay that way. "I'm going to use the restroom real quick," Jessie told Jason. "Oh ok. I'll join ya. I gotta go too," Jason responded. As they headed to the...

3 years ago
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Dealing With JessieChapter 6

It was summer, and the days marched on. Jessie didn’t resign, but she turned all the household finances, though none of her money, over to Gary. He took the department head’s job at the high school. He put his house up for sale, and, being in an upscale low property tax suburb it went quickly. He bought a new sofa bed, a clothing rack, and a small bureau for the cellar. There was a small bathroom with a shower and basin so he wouldn’t have to go upstairs for any of that. Jessie signed up for...

2 years ago
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Dealing With JessieChapter 9

So it had off to Denny’s where they ate and went back home, where he’d been told someone had pooped in the pool. They’d gone to bed, had some more fun, and Jessie went to sleep. He didn’t; she was a lot sicker than he thought. He wondered if the psychiatrist knew more than he’d shared. Jessie’s comment about semen slurping almost pushed him over the edge. Edge of what he didn’t know; at the moment he was ready to just walk out but what really scared him had been her emotional disappearance....

2 years ago
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The Softening of Jessie Part 4

Jessie woke up in the afternoon the next day. Ahhhh, Saturday morning...no school, got to love it. He rolled out of bed and stretched a bit. The fabric of his "borrowed" delicate, soft top felt much nicer on his sore chest than his rough, course t-shirts. "Man, Jason really did a number on me," he thought. With that, Jessie groggily went into his bathroom, sat down and peed. It struck him a bit odd that he was sitting to pee. After all, he couldn't ever remember sitting down before to...

2 years ago
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The Softening of Jessie Part 13

"What did you buy mom?" Jessie asked with a sense of excitement. Amanda handed her son the bag, noticing his curiosity. Jessie pulled out some of the contents. He noticed three bras with underwear attached in matching colors. "Matching bras and underwear mom?" "Yes dear, I was lucky to find some underwear that came with the bras so that you match," Amanda replied as she made little attempt to hide the bra panty sets. In Jessie's state of mind she knew she would not have...

3 years ago
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Jack Jessie part 2

Amy let herself into the house. She and Jessie had been friends since grade school, and knocking had fallen by the wayside. “Jess! Saw you were home alone, and came to hang out!” Amy was puzzled, there was part of a pizza on the coffee table, bottle of wine, and moaning coming from the back of the house. “OMG! She brought a boy over, and got her cherry popped!” Amy thought giddily. “I gotta sneak a peak, and see who it is.” So she quietly made her way down the hallway to Jessie’s room, and...

2 years ago
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The Softening of Jessie Part 17

As the two sat at the food court eating lunch, Ashley couldn't help but how much her friend had changed. He now sat there with his nylon covered legs crossed in a very feminine manner and spoke with an unmistakable high girlish tone. Wow, how could he not know what was happening to him? "How does your bra feel Jess?" Ashley asked out of the blue. "It feels good. My chest doesn't jiggle all around like it was before. I think that the bra may actually help my swelling go away by...

2 years ago
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The Softening of Jessie Part 18

"So you want to know about different kinds of panties, do ya?" Ashley asked her inquisitive friend. "Yes, you might think it's kind of weird, but I seem to have forgotten. I know I wear panties everyday, but I guess I never paid attention," Jessie replied. He felt a little odd not knowing about something he felt he should have. "Okay, let's see...these are called boy short panties. They are just like the boring old underwear boys wear, but they are frilly'd and lacy'd up a bit,"...

2 years ago
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Teenaged Jessie enters my bed and my heart

Her mother was a drunk who was usually so plastered that she staggered around the house in her baggy house dress, falling over the furniture till she passed out. Her father was abusive, not sexually but he often hit her and pushed her around and verbally abused her. He frequently brought other women home to fuck while his wife was passed out on the couch. He did not pay any attention to his daughter being around. Several times she had seen him roughly throat fucking some slut that had...

4 years ago
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The Softening of Jessie Part 19

"Here Jessie, let me help you over to that bench," Scott said as he sent the elderly couple on their way. "Good thing I was walking by here... I was just in the nick of time!" he joked with Jessie. "Scott right? Thanks for stepping in there. I was about to go off on those two. The old guy should feel lucky I didn't pound him into the pavement!" Jessie emotionally replied. "Well you do have spunk, that's for sure," Scott stated. He found the whole feisty, tough girl thing a turn...

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