Riding the Jessie Train

Being on the bottom, I couldn't really dictate the flow of events. After several minutes of blissful group sex, Jessie's husband slowed to a quick stop and pulled out. Jessie's legs collapsed as her husband withdrew, and I ceased from banging her ass after three or four more hard pumps. Then Jessie's husband got off the bed and directed Jessie to turn over. The gasping, sweat-drenched bitch did as she was told, trying to catch her breath during this brief respite for her poor abused holes.

On her hands and knees, Jessie straddled over me, her hair falling into her face as she looked down, her glistening boobs hanging down toward my chest as I put one hand on her back and the other on my cock, setting it up directly underneath Jessie's pussy. Again, I'd be going into her first.

As Jessie sank down on top of me, taking my whole shaft into her pussy, Jessie's husband suggested I go in her ass. I didn't really make sense to me if we were going to double-penetrate her again, and I was long overdue to fuck Jessie's pussy anyway, so, honestly, I just ignored him. Instead, I briefly squeezed Jessie's boobs once I was to the hilt inside her before putting my hands on her hips and beginning to lift her up and down my cock.

Again, her husband asked me to fuck Jessie's ass, but this time Jessie intervened. "I want you in my ass," she said to him. He acknowledged Jessie but, for now, stayed back as Jessie rode up and down my cock, faster and faster. Her hair and boobs jiggled as she took me inside her incredibly wet and tight cunt over and over again. We moaned in unison as we fucked for a few minutes. While I delighted in the absolute wickedness of sandwiching Jessie these two times, just having one-on-one sex with the girl of my obsession, even if just for a few minutes, was a heavenly experience.

"Are you ready for that cock in your ass?" I heard Jessie's husband say just as my sex with Jessie got really intense. As much as I wanted Jessie to be double-stuffed again, I would have been content to just let her finish me off right there. But as I watched Jessie's husband hop back onto the bed and spread Jessie's ass, drawing his cock near, I supposed it was good either way.

I slid my hands to Jessie's shoulders while Jessie's husband put both hands on his wife's hips and sank right into her ass, not really taking his time at all. Jessie cried out, possibly in pain but maybe in pleasure. Probably both, actually. As I felt that cock sliding into the hole neighboring the one I was filling, I thrust up farther into Jessie so that my balls were touching her taint again. Her husband, this time staying vertical as he knelt in front of us, was soon fully sheathed in Jessie's ass so that Jessie was stuffed in both her holes again. Wasting no time, we men went right back to fucking her.

Jessie propped herself up between the two of us as she moaned and took our double penetration. Her body glistened in the light of the room, the air in which having grown very hot. We were all panting and sweating as we had sex in that motel room. Jessie's husband and I slid in and out of Jessie's ass and pussy relentlessly, establishing the same rhythm as before.

Collapsing on top of me, Jessie slid her hands onto my shoulders and sank her nails in while she got owned at her other end. The whole time she was yelling and moaning. Her damp boobs and stomach pressed against my body, her sweat-soaked hair matted against her neck and pressed against the side of my face. Most of the time her eyes were shut, but on the occasion that I made eye contact with her my gorgeous friend, she would give me a smile that was half endearing, half wicked.

Our cocks plunged in and out of Jessie's holes for what I wish had been forever. As I pumped in and out of Jessie's twat, my hands alternated between her shoulders and her boobs, if her boobs were accessible. After just a few more minutes, I had no choice but to announce I was about to cum. With that warning, Jessie's husband pulled out of his wife's ass, and Jessie hopped off me and then off the bed. I didn't even have to say what I was going to do. All three of us already knew.

I jumped off the bed too with my cock in my hand. Jessie knelt down in front of me, pushing her hair out of her face and closing her eyes just in time for me to step up and cum on her beautiful face. I watched on, moaning loudly as jets of semen sprayed her pretty cheeks, chin, nose and forehead. By the time I was done, cum was streaming down all over her face and down to her neck.

Immensely satisfied, I sat down in a chair across the room and watched shamelessly as Jessie's husband put Jessie on her back on the bed, spread her legs and stood over her as he fucked her pussy. A couple years ago, I probably wouldn't have enjoyed watching someone else have sex with Jessie, but I had no complaints anymore, not after what I had done to her. Jessie laughed, clutching her boobs and lifting her legs again while her husband held her hips and pounded her for just a couple minutes, undeterred that his wife had another man's cum on her face. At last, he pulled out and came all over Jessie's stomach and tits until we were all spent.

We cleaned up and got dressed. I planned to come back the next morning and check out, since we had rented out the room for the entire night. Whether anyone heard us or anyone knew a devil's threesome was going on in that room, I don't know. I didn't care. I now had two incredibly hot experiences that I would never forget, and I hoped dearly that Jessie and I would do whatever we could to make these threesomes a regular thing. If only we had started back in college when we lived near each other!

Just a few months later, Jessie was back in town for Memorial Day weekend. This time, however, her husband didn't come with her. She came up with one of her brothers, actually, but this account isn't going where you might think it's going. The extent of her brother's involvement ends there.

Of course, due to the absence of Jessie's husband, I never expected any action this weekend. She did ask me to keep Sunday open though so we could hang out, but I didn't even dare fantasize about anything. Sure, Jessie was one of the hottest girls I knew and a very good friend, but she was married, and I wasn't going to interfere with her marriage by fucking her for just myself.

To my surprise, Jessie texted me the day before with the location at which to meet her. It was a motel about 10 miles south of her parents' house, where she was staying. I asked her what this meeting was about, and all she said was, "It's not what it looks like. See you then."

I still wasn't close with Jessie's husband, so I didn't care enough to check with him at the time, but apparently nothing Jessie was telling me was dishonest. Anyway, by this point in my life, I'd obviously done some pretty debauched things, so I was pretty calm when I headed to the agreed upon location, which was about 30 minutes away from my apartment, even though I didn't know what I was getting into. Jessie said it wasn't what I would suspect, but I couldn't imagine sex wasn't involved.

Room 201 was the unit to which I was directed to go. I can't even remember the name of the motel (something "lodge," I think), not that it matters, but it was another one of those cheap, two-story structures where all the rooms were accessible from the outside. The place was pretty sketchy looking, but it was a rural setting, and the time was mid-day, so I wasn't worried about getting stabbed - catching something, maybe.

As I headed up the stairs, I looked for Jessie's car and spotted it quickly, so I knew I was in the right place. As I stepped up to room 201, I started to feel nerves. I've never been confident in any type of unfamiliar situation, so my heart started to beat a little faster as I knocked on the door. After a delay of only a couple seconds, the door cracked open just an inch or two, and Jessie's bright brown eye peered through. I noticed she had latched the door, but upon recognizing me, she unset the latch and opened the door wide to let me in. I caught just a brief glimpse of Jessie, intending to check out her outfit, but my attention was immediately directed to another individual in the room.

Shaking my head, I asked Jessie if her ex-boyfriend from nine years ago was actually standing in a motel room with us. Jessie was visibly shaking, albeit only slightly, as she smiled nervously and informed me that one other person would be here any minute. Meanwhile, I was admittedly pretty rude to Andrew, as we'll refer to him, but not only was I in shock, but this guy hadn't been good for Jessie when they dated, and I didn't feel it necessary to be courteous to him even after all that time had passed.

I fired a few questions and Jessie, mainly to avoid silence and not so much to figure out what was going on, since it wasn't hard to deduce the situation. Most of her responses included profuse assurance that her husband not only knew what was going on but was OK with it and chose not to participate as he remained back home for work. I guess perhaps he had to draw the line somewhere.

I, on the other hand, would soon realize I still hadn't found my precise limit when it came to sexual relations with Jessie, and she knew it better than I did when she arranged this meeting. While Andrew and I exchanged no more than an awkward glace and perhaps a nod with a "Sup?," Jessie headed toward the bathroom. It was then that the realization of my situation began to settle in and I was able to notice Jessie's outfit.

She had her hair pulled back in a ponytail for now, which showed off her large silver hoop earrings. Her top was a strapless pink button-down that bared her midriff . Her black miniskirt looked just a bit longer than the one she'd worn for her husband and me just a few months ago, and her black, open-toe high heels were, I believe, the same ones she wore way back when we double-stuffed her the first time. We had agreed that high heels were a necessity for Jessie in these types of situations.

While Jessie was in the bathroom, the atmosphere in the room was even more awkward than when I had sat in a stranger's house with Jessie's husband two Christmases ago before my first threesome. At this point, I knew literally nothing about Andrew anymore and didn't really care to find out. I just wondered how far this meeting would go and what Andrew was willing to do. Jessie had said one more was on the way, and obviously we were all going to fuck her. I thought it was fair to consider it a gangbang at this point, but would we all just take turns or would these guys be down to double-penetrate her? Would I even be comfortable going that far with these guys? Would they want to take it even further, to a level at which even I was uncomfortable?

With all these thoughts racing through my mind while Jessie was taking way too long in the bathroom, as girls do, there was a knock at the door. I really have no idea if we waited for five minutes or an hour - I completely lost track of time, reminiscent of Jessie's and my first group sex. At the knock, Jessie bolted from the bathroom, stumbling a little in her high heels. Her makeup appeared to be about half-finished, so I knew I'd get to enjoy several more minutes of uncomfortable waiting, only with two other guys instead of one. At that moment, as Jessie opened the door, I started to entertain the thought that it was another girl waiting to be let in, a thought that got me excited. That excitement didn't last long.

The opening door revealed Ben. I hadn't seen Ben in about six years and was happy with that arrangement. I was not surprised that he would show up for a gangbang, though, and I was actually not happy at all that Jessie invited him to fuck her. Ben was a creep for as long as I had known him, and I was sure that fact hadn't changed over the years, especially now having seen him with that disturbing grin on his face as he showed up for a group fuck of one of my best friends. I guess I was being pretty judgmental though, since I was there for the same reason, but I digress.

Jessie would later explain that, much like when she first invited me to join her and her husband, she thought it would be hot to invite multiple guys to fuck her in one session and see where it went. We never really justified this one in the context of her marriage, though, since her husband was absent, but I was there and ready to go, so it was easy to just not back out. We later figured that trying something even more debauched would give us a story worth telling instead of the same double-penetration story again.

Maybe I was biased because of my friendship with her or just the fact that she was my type, but Jessie was a really hot piece of ass and very popular on top (because?) of it. I knew it wasn't a stretch that she could scroll down her contact list and randomly find a few guys who would be happy to take turns fucking her with other guys. Heck, she'd essentially done the same thing with me a year and a half ago, right? The choices of Andrew and Ben made perfect sense after I was able to think about it. The fact that she'd gotten only three tells me she either didn't try hard enough or put a limit on it. Personally, having seen first hand what Jessie was already capable of, I'm sure she could have taken another man or two.

I didn't even complain about Ben's presence, not because I didn't want to but because there was no point. Beside, by now I was in with no turning back. If Ben wasn't there to help triple-team Jessie, who would? I just accessed the depraved pervert in me to pull me through like the couple times before.

Jessie headed back into the bathroom, leaving the three of us guys together. Andrew was always quiet, which I appreciated more than ever now. Ben, not so much, and he was totally comfortable even in this context. I won't even waste space here with the stuff he was saying. I don't even care if he sees this writing. Let's just say he was eager to comment on Jessie, on us guys, on the situation and on the extent of what we were about to do. Neither Andrew nor I really acknowledged him, but it didn't stop him from talking.

Jessie was in the bathroom for probably 10 more minutes, but it definitely felt much longer. Ben was so annoying that I wasn't even aroused anymore, so it's not even like the anticipation was killing me. Well, until Jessie stepped out of the bathroom, that is.

Her makeup was complete, sure, and her hair now hung down loose around her shoulders, but the most noticeable difference was the absence of her top and skirt. She strutted out in the dim light with a huge nervous grin on her face, sporting just her black high heels and bright pink underwear. The earrings were the only jewelry she wore, which were almost completely obscured by her long brown hair anyway. The bra she wore was strapless and accentuated her pert B-cup boobs perfectly. For her lower half, she had chosen a thong. At this point, I noticed I had previously missed her pink finger- and toe nails. I think it was a brighter shade than the last time.

Jessie's appearance was the only thing better than the fact that Ben finally went quiet. I can't speak for the other guys, but I was stunned silent. I forgot the other guys were even there as I gazed upon the 28-year-old, slender, almost naked brunette beauty before me. Her body looked amazing, especially considering she'd given birth once. Obviously I'd seen Jessie naked before and in some pretty hot poses, but there was just something about her in that attire and in this situation that made my heart stop.

More and more, this rendezvous reminded me of my first time with Jessie and her husband. The awkwardness with the other participants, the way my brain inconsistently gauged the passing of time and how my vital body functions fluctuated all combined to excite and entice me as I embarked on a genuinely new experience with the object of my obsession, an experience about which I'd personally never dared to entertain.

Before we did anything, Jessie demanded we turn in our cell phones. Since we'd all be getting chances to observe while not participating, Jessie didn't want any pictures or videos going online. None of us gave her any trouble as she put them in her purse that was on the nightstand, though the right picture or video would have been really hot.

Once the phone issue was settled, Ben made the first move, which instantly gave rise to jealousy within me, but it was my own fault. Andrew and I just stood there like deer in headlights while Ben was the first one to break the spell and get started. He walked up to Jessie, who giggled as he grabbed her arm and pushed her over toward the twin bed. By the time Jessie was at the bed, Ben had his gym shorts down his knees and his cock out. Jessie bent over the bed, propping herself with her elbows on the mattress, turning her head to look over her shoulder through her hair that was coming down over her face as she watched Ben use one hand to push Jessie's thong strap aside and used the other hand to guide his cock against Jessie's pussy. He didn't give Jessie so much as the courtesy of getting spit on his dick before he poked it inside her, then switched his hands onto her hips and thrust forward until his balls touched her clit.

Watching Ben fuck Jessie wasn't my favorite thing, but it was hot to watch Jessie take a dick while bent over a motel bed and still in her underwear. She smiled and held her head straight up as her body rocked back and forth with Ben's steady pumps in and out of her. At this point, I remembered how the fan had muffled some of the noise last time I was in this setting, so I went ahead and turned it on before going back to watch Ben and Jessie have sex.

After a couple minutes, I found myself touching myself a little, so I just undid my jeans and let my cock out but refrained from stroking it for now. Meanwhile, Andrew had sat down for whatever reason and just watched. I couldn't help but notice the bulge in his jeans, betraying the fact that he was enjoying the party.

After a couple moments of moaning and fucking my favorite friend, Ben reached up to undo Jessie's bra, letting it fall onto the comforter as he slowed down in her for just a couple seconds. Then he put his hands on her boobs and went back to taking deep, hard strides into her for several more minutes until Jessie told him it was someone else's turn.

Ben gave Jessie a couple more hard thrusts and shouted as he ground up on her and held his cock inside her for a moment before finally pulling out. His cock shimmered with Jessie's juices in the dim light as he stepped back. I immediately made my move, already standing and having my cock out while Andrew remained seated.

Upon seeing me approach, Jessie pushed herself up onto her hands, her arms rigid, and grinned at me. I stepped up behind her and leaned forward to first pull Jessie's thong down her legs, not wanting to contend with the article at all. Now I could see that Jessie's pussy was wet and swelling from both having been fucked already and the anticipation of being fucked again. I decided to leave the thong around Jessie's ankles for now. It looked good with her sexy high heels.

My hands shook as I still adjusted to what was going on. I'd never fucked a girl with others watching and, while group sex wasn't new to me, it was still a pretty fresh experience. As I held my cock, Jessie threw her hair back over her shoulder by swinging her neck and looked ahead, arms straight, legs rigid and spread for me. She was posing, knowing she wasn't just giving me sex but also performing for two other guys. As my erection protruded straight out, longing for Jessie's twat, I let my pants drop to my ankles and quickly threw off my shirt, knowing the room would be getting pretty warm soon. Then I put my left hand on Jessie's bare back as my other hand wedged the tip of my cock into her opening.