Riding the Jessie Train

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Long-awaited follow-up session leads to more debauchery.
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dpingjessie
dpingjessie
1,144 Followers

It was late afternoon, and Jessie and her husband were on their way from dropping off their son with Jessie's brother. As they took care of the kid, I checked into a Motel 6 that was just five minutes away from my apartment. I waited in the room for about 20 minutes before the two of them walked in together, Jessie smiling as she pulled off her long, heavy coat that not only kept her warm in the 10-degree weather but also covered up her outfit that would have been inappropriate for most occasions. I smiled back at her, already getting hard from just seeing her, knowing what was about to happen. Her husband and I, meanwhile, barely acknowledge each other.

As soon as Jessie's coat hit the floor, I was stunned. Her outfit may not have been quite as arousing as the Santa get-up she had sported last time, but her attire was very boner-educing regardless. She wore a tight, white halter top that almost covered her belly button to go with a dark gray pleated miniskirt that left little to the imagination. For shoes, she donned silver six-inch high heels that showed off her bright pink pedicured toenails, which matched her fingernails. Topping it all off, around her wrist and ankle were the same bracelets she'd worn last time, in addition to just the right amount of makeup on her face that was framed perfectly by her brown hair, which she had curled just slightly to curve around her cheeks and bend outward as it approached her shoulders.

Jessie walked straight to the queen size bed in the middle of the room and sat down on it. Meanwhile, her husband had the sense to turn the fan on all the way up to mask some of the noise that would be coming from our room. Even though it was just now turning dark outside, there was no way of knowing who would be around to hear our escapades, even through the cement walls. The first couple minutes were awkwardly silent, but Jessie broke the silence with a line that she had clearly rehearsed ahead of time and probably stolen from a porno.

"Do you know what my favorite cookie is?" Jessie began as she reached for the hem of the halter top. She immediately answered the question for us: "Oreo." She smiled wide across her face, holding in a giggle. Her voice cracked a little as she spoke, betraying her nerves. Also I'm not sure, but I think that reference more suitably depicts two black dudes with a white chick, and Jessie, being only slightly tan, was the darkest one in the room. Anyway, despite Jessie's lack of confidence in delivering, she said it well enough to turn me on just a little more than I'd already been. Even if her actual use of the line wasn't flawless, after this session, I'd always remember it as if it were.

Not hurting her attempt to be sexy was that she was pulling off her shirt as she sat on the edge of the motel bed. Unlike last time, there was no delay in Jessie's presentation. She had arrived to the motel already prepared, and we didn't feel the need to consume alcohol to push us on this time. I'm not sure I could have carried through the first time without those couple shots I took, even though I almost never drink. This time, though, with the sights and sounds of the Jessie sandwich her husband and I enjoyed more than 13 months ago forever etched into my brain, I had all the motivation I'd ever need.

The anticipation of what was about to happen was arguably greater than last time, being free from the anxiety and most of the awkwardness. While the thrill of doing it the first time held an element that could never be matched, the build up to this follow-up session was almost unbearable in the best way possible, now that it was finally occurring. Over the past 13 months, I wanted nothing more than to relive the blissful experience of double-penetrating my favorite friend of 10 years, and this time I knew exactly what to expect and had no fear of disappointment. Of course, it was still a little weird leading up to it, as I would probably never be completely comfortable around Jessie's husband - or, in the context of intercourse, any other man for that matter. However, those qualms very obviously didn't end up deterring me last time, and they most certainly would not hold me back this time, given my determination.

Double-penetrating Jessie had always been a fantasy of mine, but now that the fantasy had been fulfilled once, the burning desire to sandwich Jessie only grew. I had already been a little obsessed with her beforehand, but now that fixation bordered on desperation to do it again. On this freezing day in early February, I stood in that motel just moments away for abating that frustration. My heart was racing and my mouth was dry even before we undressed.

It was no surprise what was about to happen next as Jessie threw her top away, revealing a white frilly strapless bra. Interestingly enough, none of us in the room had actually once specifically mentioned that we were convening for a double penetration threesome. To this point, Jessie's Oreo reference came the closest to a definite allusion. After carrying out the debased act once, it was just a matter of saying where and when for the second time. The "what" was mutually understood.

We had all thoroughly enjoyed the raunchy, ungodly group sex last time and agreed immediately to do it again. However, different circumstances stalled the follow-up session. First of all, there was the initial awkwardness that comes with banging a girl in a devil's threesome after almost a decade of mostly platonic friendship. On my part, like I implied already, I never felt comfortable with Jessie's husband to begin with. Getting carried away with teaming up on his wife only complicated that issue, especially when I was forced to communicate with him over the months.

Naturally, I had no qualms with talking to Jessie about doing terrible things to her slender 5'5" frame and actually, over the months, often attempted to steer our conversation toward the subject, in part because it turned me on and in part because I hoped to expedite a fresh session. Unfortunately, Jessie was less eager to talk about it than I was. She insisted that she loved the experience and had no regrets, but her quickly dropping the subject made me suspect that she felt uncomfortable or dirty - even guilty.

After a couple months, Jessie finally did admit that she had felt a little awkward moving forward after such outrageous behavior, but she was telling me now that she had gotten over whatever guilt and shame there was. We started planning as early as March of last year, which was when Jessie communicated that she and her husband were ready to add a little excitement to their marriage again. It was just a matter of a time and a place.

Therein lay the reason for the delay. Almost a full year passed between Jessie's first text to me stating she was ready for another double penetration and this moment where she began to disrobe in a cheap motel as she not-so-confidently quoted porn. First, Jessie and I lived more than 500 miles apart, and sometimes that obstacle felt like the least of them. We both had good jobs and firmly rooted lives in other states, not to mention Jessie had a child. When she did visit, she always stayed with her parents, a situation that didn't present an opportunity for disgraceful sex. I, on the other hand, had two roommates at home and had no excusable reason to take off work and head hundreds of miles south to join a dude in banging his wife - though I started to consider it a few times. Most of the time, her husband just couldn't get off work. At least Jessie worked online from home, so her job was never an issue. Otherwise, we might still be waiting.

The stars had kind of aligned for us when Jessie's husband and I fucked Jessie in unison that first time. It wasn't until near the end of last year that we realized we needed to just make it happen, but even then, for one reason or another, the plans fell through. Either the couple couldn't make the trip or one of us couldn't find the time when Jessie and her husband were in town. This past January, we had everything in place, which is when we first settled on the motel idea, and then Jessie got very sick. Finally, in February, they made the excuse to visit for Jessie's mother's birthday.

Which brings us back to Motel 6. Jessie's husband and I watched on in silence as Jessie reached around her back. We didn't really respond to the Oreo comment, but the bulges in our pants were only affirmation Jessie needed as she unhooked her bra. Now my pants were uncomfortably tight as Jessie threw away her bra, baring her lovely boobs to me for just the second time in my life. She then flung her hair back over her shoulder, appearing to gain confidence from being topless, before planting her hands on the mattress and looking sharply at us guys with those big brown eyes.

I stood there for a minute in some sort of a trance, but Jessie's husband broke me out of it by muttering something as he took off his pants. Without giving it much thought, I followed his lead, and, in a minute, we were both naked. It was uncomfortable at first, but I stayed focused on Jessie and what I was there for. That kind of concentration had already driven me through this same debauched behavior before, after all.

Jessie's husband stepped up, and Jessie immediately took his cock in her hand and began to stroke it. With her free hand, she beckoned me over. I was a little uneasy with being that close to and at eye level with her husband in this context, but, again, concentration was key. I knew in just a few moments those concerns would be far removed from my mind.

Jessie's husband and I stood angled in front of Jessie as she stroked both of our cocks simultaneously, looking up at us and raising her eyebrows seductively as she ensured that we were hard enough for her, not that there was any doubt. As she held me in her left hand and her husband in her right, she started by sucking her husband's cock for a moment before switching over to mine. As soon as Jessie took me into her mouth, her hand still rubbing the base of my dick, I flashed back to the only other time Jessie sucked me off and all the wonderful things that happened that same night. As Jessie's head moved back and forth, lubricating my entire prick with her saliva, those aforementioned anxieties began to fade away.

Jessie alternated between blowing the two of us for several minutes. I enjoyed the sound of her slurping our cocks and appreciated her effort to stroke me when I wasn't the one in her mouth. The only other sounds were moaning from Jessie's husband and me and the occasional gasp for air from the beautiful, topless brunette.

The next words spoken were from Jessie's husband, who said, "Do you like sucking two cocks?"

Her response gave me chills as I anticipated its becoming reality: "I can think of something better for them," she said, briefly holding both our cocks up to her mouth but careful to keep them from touching as she licked the tips of them both. "How about one in my pussy" - she took another lick - "and one in my ass?"

The next thing I remember is I was lying on my back on the bed as Jessie stood beside it, removing her miniskirt and then her thong while her husband took a small step back. With those garments removed, I cannot accurately describe how hot Jessie looked right then, dressed only in her high heels and some jewelry while her hair and makeup accented her beauty perfectly. My excitement hit a fever pitch when Jessie climbed into bed with me while I wondered which hole I would be treated with first.

Just Jessie's naked body's getting near me made my heart nearly explode from exhilaration. Our eyes met and lingered, Jessie's grin spreading across her face as she prepared to position herself over me. It turned out that I was getting her ass first, as Jessie faced away from me and kind of crab-walked over me, supporting herself in the air by all four limbs. At this point, I took over for her, using one hand to position my cock in line with her ass and using my other hand to guide her downward until my cock slid between her ass cheeks and into her tight, dark hole. I wedged just enough of my tip in first while Jessie adjusted herself. She planted her heels into the comforter beside either of my knees while her hands pushed into the mattress beside my shoulders. I had to duck my head a bit to avoid Jessie's hair in my face as I held up my head and watched Jessie's body sink lower onto my cock.

Jessie cried out a little as I slowly shifted her down. I was careful to be gentle, not knowing how much anal experience she had. Her asshole wasn't as tight as I remember though, since the only other time I had been inside it was when there was already a prick in her twat. After just 30 seconds or so, Jessie was sitting on my balls with my cock firmly stuffed in her shitter.

It was only my second experience with anal myself, the double penetration with Jessie 13 months ago being my lone run at it. I'd never found fucking a girl's ass to be much of a turn-on unless her pussy was being fucked at the same time. When it came to Jessie though, I didn't care if it was her ass, face, tits, pussy - as long as I got to put my cock in Jessie, I would sign up.

Jessie and I were both breathing hard as we slightly realigned our bodies to prepare for an evening of wild sex. I put my hands on Jessie's hips while she continued to plant her hands and feet on the mattress. Then I assisted her only a little as she lifted her body and began to screw me with her ass.

I cursed as Jessie slid up and down my cock, taking it deep inside her butt. I hadn't fucked her in the ass before without her husband in her pussy, so this sensation was kind of a new one for me. I have to say that screwing her ass felt great. I wouldn't prefer it to her pussy, but there was something to say about the different sensations.

Jessie's hair swung down toward my face as Jessie bounced on my cock, going a little faster as she grew more comfortable. I lifted her up and down a bit, but Jessie did most of the work. I kept my gaze on my cock's plundering her ass for a couple minutes but eventually rested my head on the pillow and just let the feelings take over.

Jessie's husband let me fuck his wife's ass for four or five minutes until he invited himself on the bed with us. He stood up between my and Jessie's legs as we all awaited the real fun. It was time for the main entrée: a hot, delicious Jessie sandwich.

I looked on in disbelief as Jessie lifted her legs straight up into the air and spread them wide for her husband while I held her still and helped balance her on my cock. Even though I had performed this same shameful act with these same individuals before, I couldn't believe it was actually happening here. My heart started to pound again as I watched Jessie's husband kneel down in front of us and, holding himself up by one arm, guide his cock into Jessie's remaining vacant opening.

Jessie moaned loudly as her husband leaned forward, sinking his cock into her pussy slowly, inch by inch. Before, I had been the second one to enter Jessie, so it was another new feeling for me as Jessie's husband's cock slid up against mine on the other side of the membrane that separated Jessie's holes. He was gentle out of concern for his wife, but it was only a minute at most until he and I were both balls deep in his woman.

All three of us cursed, Jessie's cry being the loudest. I sank my nails into Jessie's hips as I remained still in her ass for just a moment longer. I looked up with delight at Jessie's legs, outstretched over her husband's shoulders, the heels of her shoes pointing toward the ceiling. Just like last time, there was so much sexiness to take in that it wasn't difficult anymore to look past incidental contact with the other man.

Once we were all settled, Jessie left her left arm planted nearby my head but reached up with the other one to clutch her husband's back as she adjusted to being sandwiched for the first time in more than a year. Her husband lay on top of her, leaning over her right shoulder, while I positioned my head under Jessie's left shoulder and looked up at her sexy legs and heels as they reached for the sky. Now that I was as turned on as I could ever be, I started to thrust up into her ass.

Jessie groaned as my cock stretched out her tight asshole, which was even more constricted now that the adjacent hole was stuffed as well. I did the best I could with the weight of the two bodies on top of me, which was also new exposure for me. I liked it, not so much because another man was a significant percentage of that weight, but because Jessie's back was pressed close against my chest and stomach. As I was still getting the hang of my predicament, Jessie's husband went to work, pulling his hips back and then slowly sinking his cock back into Jessie's pussy.

I wouldn't say double penetration is like riding a bike, especially since we weren't very seasoned in it, but it didn't take long at all to get into the rhythm we had worked out last time. Whenever I felt the cock in Jessie's pussy slide into her, I pulled back in her ass. Then I'd wait until I felt Jessie's husband start to retract before I'd thrust back into my friend. I also quickly figured out that I was able to fuck Jessie better by sliding my body horizontally instead of thrusting back vertically, since I was kind of pinned down.

After a couple minutes, we had it together. With Jessie sandwiched between us, her head close between ours, legs spread and outstretched, her husband and I started to fuck her harder and faster. I continued to pace myself in reference to her husband's cock and kept up pretty well. Our cocks moved like pistons in and out of the panting, moaning bitch as we boys grunted with her. Without Jessie's legs between ours to separate them, occasional contact between us men was sometimes unavoidable, but we hardly noticed as we focused on the wonderful reality that we were double-penetrating this hot girl.

Almost right away, my whole body was perspiring, having Jessie's body pressed close, pinned against me by her husband's thrusting body. I soon noticed that Jessie was coated with sweat as well. I could only imagine how warm she felt being the meat in this delicious sex sandwich.

We double-fucked Jessie hard and fast, sliding in and out of her ass and pussy steadily and firmly for several minutes. All my senses felt sharp as I took in the reality that, after more than a year of frustration, we were simultaneously sawing in and out of Jessie again, which I had so desperately desired to do. Looking up only drove my lust on as I saw Jessie's legs and feet bouncing in the air as our collective mass of flesh bounced on the mattress in this cheap motel to the soundtrack of the heavy breathing of all three of us. While Jessie's husband's current position was my decided favorite for myself in a threesome, I did enjoy the view of Jessie's legs in the air from this perspective, something you miss out on when you're on top.

Eventually, the audio was more than just heavy breathing. I don't think any of us realized how loud we were getting. Jessie especially was moaning and shouting, using her fair share of profanity. The fan could muffle only so much noise. Granted, it was just early evening by this point, but we were probably being heard and were just oblivious to it in these moments of passionate, hot, dirty group sex. Not only was our moaning and yelling emanating from the room, but the squeaking mattress was also quite noisy.

Jessie's hand gripped the comforter right by my head as she continued to clutch her husband's back. At this point, I could also hear the squelching of Jessie's lovely ass and pussy as we boys deftly ravished them. For how awkward we were around each other, Jessie's husband and I sure made a good team when it came to fucking a girl together. Adding to the sounds were the rattling of Jessie's jewelry and, of course, the smacking of damp, sweaty flesh.

dpingjessie
dpingjessie
1,144 Followers