Riding the Jessie Train

Jessie cooed as my right hand joined the other on her back and I slowly thrust into her. I sighed loudly, not really aware of the guys who were watching me. Once I was inside Jessie, I didn't really care who was watching or how many. Jessie's tight, wet twat squeezed on the full length of my cock once I sank all the way into her, making everything in the world right. She was so intoxicating that I began to question the limits of what I would do with her.

I proceeded to make love to Jessie's cunt, leaning over top of her, sliding my hands up and down her back as I pumped in and out of her, slowly at first. Jessie moaned with me and held her head up by mine as I fucked her over that bed for just a few fleeting moments before Jessie reminded me to share.

Reluctantly, I pulled out and stepped back to allow Andrew, now fully disrobed, step up behind Jessie and take his turn. For the next half hour or so (probably longer; I lost track of time), we took turns with Jessie in that order. In all, we each got three goes with her alone. When I got my second round, Jessie stepped out of the thong that had still been around her ankles and let me flip her onto her back, lifting her legs up and resting her ankles on my shoulders.

Jessie put her arms over her head and gripped the comforter as she prepared for my entry, her hair splayed around her head. Sweat glistened on her sexy body while her boobs heaved up and down. She looked at me with those piercing brown eyes as I slid my member back into her used cunt. Leaning forward, I grabbed Jessie's boobs as I nailed her hard right from the start. My balls slapped against her taint as her body shook and her legs bounced against my shoulders. I started to pant and sweat as I plunged harder and faster into her over and over again until I forced myself out of her to avoid cumming too soon.

Andrew and Ben fucked Jessie in the same manner. Halfway through his third session, Ben pushed Jessie up onto the bed and, never taking his cock out of her, slid up with her, lying her head on the pillow. Then he continued to fuck her while her legs stretched out toward the ceiling, her hands holding onto the headboard.

"Fuck me until you cum all over my face!" Jessie yelled as Ben gave her the business. He did just as she said, his body slapping against hers as he pressed up against her, the bed creaking beneath them as they had sex. Finally, Ben pulled out and knelt over Jessie, groaning as he jerked himself off until he came all over Jessie's face.

It was my turn. I couldn't help but admire Jessie's cum bespattered face, even though it was another man's semen. As I lay on top of her, I was careful to not get any of the jizz on me, but Jessie made that endeavor challenging as she wrapped her arms and legs around me, pulling me close against her immediately when I sank into her. Undeterred, I thrust hard and deep into Jessie in rapid succession, smacking my damp flesh against her own. My balls slapped against her taint as the squelching of her wet pussy joined the sounds of our sex, the creaking of the bed and the fan.

With all the stimulation, it wasn't long until I felt my balls tighten. Intensely turned on, I whispered into Jessie's ear if she wanted a double penetration. "Maybe later," she gasped. A moment ago, I don't know if I was comfortable double-penetrating Jessie with one of these guys, but I was too turned on right now to pass up the opportunity or at least not pursue it.

Breaking out of Jessie's cage of limbs, I pulled out just in time to point my cock at her face as ropes of cum shot out. The sweat-soaked bitch quickly grabbed my erupting cock and stroked it fast, assisting me as semen splattered all over her forehead, nose and eyelids. A few shots streaked through her hair near the end until the last couple ropes dripped onto her neck.

Andrew fucked Jessie lying down on top of her as well. For Andrew, Jessie spread her legs and rested them over his hips while she held onto his shoulders. Andrew gave her the full force of his cock for just a couple minutes before he pulled out and shot his load onto her tits first and then the rest on her face to accompany the two helpings that were already there.

Andrew backed away, joining us two other men, as Jessie got off the bed and stood to her feet. Her face was a masterpiece, all but covered in cum that was now dripping down her face and as far as her stomach after a minute or so. Before a single one of us could reach for our clothes, Jessie stopped us.

"Rest up," she said. "We're not done yet." With those words, she winked at me. Even though I was spent, I was getting turned on all over again, hoping Jessie was referring to what I thought she was referring to. I wasn't sure before but I was committed now to some more wicked group sex. I just hoped the guys would be on board too.

Jessie strutted off to the bathroom to clean up the mess on her face and freshen up, meaning we guys were going to have to wait entirely too long in either silence or with Ben's inappropriate comments. It turns out, the silence didn't really bother me, and Ben's talking was easy to ignore as I was intently focused on getting myself prepared to perform once Jessie came back. I wanted to be ready to go so as to not miss this opportunity. I decided I really wanted to Andrew and Ben to double-stuff Jessie while I watched, since just the thought of seeing that act was doing a good job of getting me hard again already. Sitting back and watching Jessie get sandwiched was a long-time fantasy of mine and one I hadn't been able to fulfill despite having double-fucked her twice myself.

After 20 minutes or so, Jessie reemerged from the bathroom. She looked as sharp as she did before only her hair looked a little less fresh. Otherwise, she had cleaned off the cum and sweat and had reapplied her makeup. She was still naked, of course, except for high heels and earrings. We guys were all still bare too.

"Which of you guys is into double penetration?" Jessie asked, making my heart flutter with delight and anticipation. "I know you are," she added, looking directly at me. To no one's surprise, Ben raised his hand and voiced his affirmation to do the dirty deed. If I were shameless enough to do something, Ben certainly was too.

Andrew, on the other hand, stayed silent, but Jessie said to him, "I'll come back to you. You owe me this much." I never found out what was being implied there. Maybe it referred to the fun she just gave us or maybe she was referring to something from when they dated years ago.

We mutually agreed that Ben and I would take Jessie first, since we were eager to do it, while Andrew was a little uneasy. As we got into the bed, Ben asked me if I'd double-penetrated Jessie before, based on her comment to me a minute earlier. I answered that I'd done it with her twice now. I think I earned his instant respect if I didn't have it already. "Wow," he said, "just congrats, man."

I let Ben, who, needless to say, was hard again, lie down first. I then encouraged Jessie to give him her ass. In a double penetration, every position is good, yes, whether ass or pussy, on top or on the bottom. However, my clear favorite was on top, in Jessie's pussy. Jessie gave me no resistance and straddled Ben, who held onto her waist as she planted her feet on either side of his hips. Then she grabbed his cock, positioned it and then pushed the head into her asshole before letting go and slowly sinking her down until she was sitting on his balls.

Ben and Jessie cried out from the sensation, and Jessie leaned back, propping her upper body with her arms while Ben ground up against her and adjusted to her tight asshole. Ben's hands moved up to Jessie's boobs while Jessie looked up at me and welcomed me right in by beckoning me with her hand and lifting and spreading her legs. I can't even describe how hot she looked, and that sight wasn't even the best thing I'd see that day.

Wildly turned on and without hesitation, I climbed between Jessie's legs, hovering over her and not giving a damn if my legs accidentally made contact with Ben's. After you've double-fucked a girl a couple times, you get over some of the homophobia while remaining confident in your sexual orientation. Brazenly, I pushed my cock into Jessie's pussy, which was tight still even after being ravaged earlier. Once the first inch was in, I put a hand on each of Jessie's ankles and then slid to the hilt inside her, knowing I had bottomed out in her once my balls touched her stretched out taint. Less than an inch separated Ben's and my testicles, but it was enough distance for me to remain comfortable.

Jessie practically screamed as she was sandwiched for, to my knowledge, the third time in her life. If anyone was close by, Jessie's scream was heard, but no one ended up disturbing us. I smiled at Jessie as I began to thrust in and out of her cunt, and she smiled back, mouth agape and eyes gazing endearingly into mine as she balanced herself on Ben's cock in her ass and held herself up by her arms.

Ben took a minute to adjust to Jessie's asshole with my cock stuffing the hole right next to it, so I got kind of a head start at fucking Jessie. To help his case, he slid his hands from Jessie's boobs to her hips, giving him a better grip on Jessie as he sought to plunder her ass. Once Ben started to stroke in and out of Jessie's ass, I let go of her ankles and lay down on top of her, my chest smashing her boobs as I pushed her back against Ben's chest, my head over her left shoulder. Ben kept his head over Jessie's other shoulder, and now we had Jessie firmly secured as the meat in our sandwich.

I put one hand on Jessie's shoulder, not far from Ben's head. My right arm slid under the pillow. We boys did our best to avoid contact with each other, but each of us stayed focused on Jessie in between us, which, as always, evaporated any anxieties that come with a devil's threesome. Now that Jessie was pressed between us, our cocks buried deep inside her, filling both her holes, we were ready to give our bitch the fucking she needed. I had already been slowly stroking in and out of her cunt, but my lust grew more wild as I felt the other cock begin to pump in her ass. After a couple experiences with double penetration, the feeling of that other cock on the other side of that membrane didn't weird me out at all anymore.

It took us a couple minutes to angle our hips right and get used to thrusting into Jessie's constricted holes, but once we had it down, we were sawing in and out of Jessie firmly and steadily while all three of us grunted and yelled. With each passing moment we thrust faster and faster, our balls taking turns slapping against Jessie's taint, which was nice and taut, thanks to our cocks' filling her holes and her legs held up and spread out. Eventually, Jessie bent her legs at the knees so that her feet hung down behind my back while she continued to prop herself up, but my access to her cunt remained unhindered.

I was in my glory as Ben and I took turns in Jessie's holes. By now, Jessie lay flat back against Ben, her head on the pillow, arms out and hands gripping the comforter while her legs continued to dangle over my hips. Her body was soaked with a combination of her sweat and that of two other men as she slipped and squirmed, being pressed tightly between us. As sweat dripped down my forehead, I pushed myself up, sliding my hands onto Jessie's boobs and looking down at her. When her eyes opened in mid-moan, she saw my gaze at her and lifted up her head slightly, smiling. She squeezed the comforter and continued to smile through our double penetration of her, which delighted me.

My eyes then scanned down past her pretty gaping mouth, from which leaked sexy moans, down to my hands on her boobs, which had drops of sweat glistening between them. I continued to her shining stomach and finally to her spread legs and stuffed pussy that was taking a steady pounding from my stiff member. Still thrusting into her, I leaned back to get a glimpse of her cute taint and pummeled holes, of Ben's and my cocks sawing in and out of her.

At that moment, I wanted desperately to see the whole pictures. While being on top of Jessie and in her pussy in a double penetration was surpassed by nothing, I at least wanted the opportunity to just sit back and watch all of Jessie as she was stuffed in both holes. I looked over my shoulder and asked Andrew to take over for me, but he was hesitant at best. Jessie then pushed herself up, forcing my hands down to her waist near Ben's hands, and she threw one arm over my shoulder as she looked at Andrew and told him to get over here. It's not like he didn't like what he saw, after all; his full mast dick was out for all to see.

Before Andrew even committed, I let go of Jessie and pulled out of her sopping pussy, which made a sucking sound when I exited. Meanwhile, Ben never stopped thrusting into Jessie's ass, only picking up his pace once I freed up the hole next to it. When I got off the bed, Ben grabbed Jessie's boobs again and really hammered away at her ass, making her scream as she fell back onto his chest, clutching the blankets again and digging her heels into the mattress. Andrew was still being reluctant as he and I watched Jessie take an anal pounding, but both Ben and Jessie called Andrew out until he stepped up to the bed and got involved.

I pulled up a chair and almost came just from the thought of what I was about to see. Jessie grinned wickedly as she propped herself up again and watched Andrew approach. Andrew got between Jessie's legs, at which point Jessie lifted her legs and spread them wide, and Ben slowed down to a stop from his fucking temporarily. As I sat down, I struggled even to breathe as Andrew's erect cock pushed into that pretty pink pussy I had just been inside.

Jessie threw her head back and screamed as Andrew slowly slid his member into Jessie's pussy, which I knew from experience was nice and tight, thanks to the cock in her ass. As always, they took a minute to adjust and position themselves, but before long, the boys were giving an honest effort to fuck both of Jessie's holes. I had to refrain from touching myself for a little while so I wouldn't cum and then not be able to enjoy the situation quite as fully.

Watching Jessie get double-penetrated was everything I had ever hoped it would be. At last, I didn't have to see just her upper body or just her backside or just her legs and feet. I could see all of it at the same time, including her taint and filled sex holes. As the two men took turns thrusting into her, Jessie held herself up between the two of them, letting her head fall back, her hair in Ben's face, as she spread herself out and let both men have sex with her simultaneously.

Jessie lowered her legs under Andrew's arms and around his waist. In response, Andrew leaned forward over her left shoulder and began to slam into her even harder while Ben tried to match Andrew's thrusts. The boys sawed in and out of my beautiful friend, whose legs bounced in rhythm with the men's thrusts. The air was filled with the sounds of the squeaking bed, slapping flesh and moaning voices, while the smells of perfume, sweat and sex helped paint the picture as well.

Jessie took the team-fucking so well that she could have been a porn star for all I cared. Amid the threesome, she looked over right at me and laughed demonically in amusement. "Do you like watching me get double-stuffed?" she asked me. In response, all I could manage was a nod, since mouth was entirely dried out. By now, I couldn't help but masturbate as I watched this Jessie sandwich. Just like food, looking at it only made me want to consume it, and all of a sudden I wanted to be back inside her. It's not like I was going to complain though: I had front-row seats to the hottest, albeit most degenerate, sight I'd ever seen.

After several minutes of intense group sex, the boys decided to switch holes. They pulled out for just a moment, flipping the used whore onto her hands and knees. Ben immediately stuck himself in Jessie's twat before putting his hands on her shoulders and letting her sink down on him. Just as Jessie's clit reached Ben's balls, Andrew's cock was already pushing to the hilt inside Jessie's ass as he held her hips.

The boys grunted, and Jessie moaned shrilly as she took two cocks all the way inside her so that she was completely stuffed. I jerked off harder, holding off an orgasm probably only because I had already gone once today. Within seconds, Andrew and Ben were taking turns in Jessie's holes again, double-penetrating her while her body remained propped between the two of them. They pumped harder and faster into Jessie, rocking her body back and forth as they nailed her. I watched for just a few minutes until I realized we had the opportunity to stuff all of Jessie's holes. Without warning, I got up and headed to the bed.

There wasn't really a way to carry out this idea comfortably. I'd inevitably be in close proximity to both Ben and Andrew, but I just couldn't pass up this chance. While the other guys continued to roughly pound the squirming female, I stood beside the bed, next Jessie's head - and Ben's head - and offered Jessie my cock.

I looked down steadfastly at Jessie's face as she, without a word from anyone, dutifully opened her mouth and let me stick my prick in it. From up here, I could really distinctly hear the slapping of sweaty flesh and the squelching of Jessie's poor, overworked sex holes, not to mention that the bed sounded like it was going to break beneath the three of them. I noticed how sweat was dripping all over Jessie, how her hair, once so pretty and styled, was now a matted, dirty mess. The gross but hot sound of two men slamming into her sweat-coated body was really something to hear.

Also overpowering were the smell of sex and the heat generated by all this fun. It was a lot to take in as I watched Jessie impressively suck my cock even though she was already struggling to keep up and catch her breath with the pounding she was taking. I was careful to not look below or above Jessie's head, but my eyes did travel down her body to her other end where two male bodies were thrusting into and smacking against her as the three of us men plugged all her holes. Occasionally, I'd look as far down as her feet in those high heels, which bounced slightly on either side of the other men's legs as the bed creaked up and down beneath them.

Eventually, I was doing the work along with the other guys, sliding my cock in and out of Jessie's pretty mouth, against her wet tongue. Jessie stayed as still as she could and just let us fuck her. Most of her effort was concentrated on holding herself up and not suffocating on my cock while each of us guys pushed in and pulled out of our designated hole over and over and over again.

At last and with no warning beside a loud moan, I started to cum. My body had reached sensory overload and could no longer take the sounds, the smells and, most of all the sights. I shot off once inside Jessie's mouth and then pulled out, letting her gasp for air, and launched off a few more good shots onto her left cheek before letting the rest splatter within her hair. Since I'd had one orgasm already, this one wasn't as impressive, but I was still surprised at how much cum I'd managed from being so wildly turned on. I tried to ensure none of my cum was wasted on the sheets or, worse yet, the man beneath Jessie, but I avoided checking.

I backed away, and, about a minute later, Ben came inside Jessie's pussy. Most likely Ben's orgasm on one side of the membrane pushed Andrew over the edge on the other side, and both boys were cumming inside Jessie's holes, moaning loudly as they finished double-penetrating her. Jessie was laughing, feeling two men explode inside her for undoubtedly the first time in her life. Meanwhile, I was sitting back in the chair, cooling off and taking in the sight of the two men grinding against my hot female friend as they shot off inside her together.