Riding The Jessie Train free porn video

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Introduction: The following is a follow-up to the account described in my previous story starring Jessie. It was a long-time coming. While much of this story is true, we added a lot to it to make it more worth writing, so I didnt feel right categorizing it as a true story. Again, in the same interest, preparatory and hygienic details were omitted. It was late afternoon, and Jessie and her husband were on their way from dropping off their son with Jessies 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 Jessies 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 shed 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 Im 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 Jessies lack of confidence in delivering, she said it well enough to turn me on just a little more than Id already been. Even if her actual use of the line wasnt flawless, after this session, Id 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 Jessies presentation. She had arrived to the motel already prepared, and we didnt feel the need to consume alcohol to push us on this time. Im 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 Id 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 Jessies husband — or, in the context of intercourse, any other man for that matter. However, those qualms very obviously didnt 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, Jessies 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 devils threesome after almost a decade of mostly platonic friendship. On my part, like I implied already, I never felt comfortable with Jessies 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 55 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 Jessies 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 didnt 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 couldnt 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 Jessies husband and I fucked Jessie in unison that first time. It wasnt 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 couldnt make the trip or one of us couldnt 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 Jessies mothers birthday.

Which brings us back to Motel 6. Jessies husband and I watched on in silence as Jessie reached around her back. We didnt 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 Jessies 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.

Jessies 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.

Jessies 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 husbands 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 Jessies 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 wasnt the one in her mouth. The only other sounds were moaning from Jessies husband and me and the occasional gasp for air from the beautiful, topless brunette.

The next words spoken were from Jessies 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 Jessies naked bodys getting near me made my heart nearly explode from exhilaration. Our eyes met and lingered, Jessies 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 Jessies hair in my face as I held up my head and watched Jessies 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 wasnt 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. Id never found fucking a girls 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 didnt 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 Jessies 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 hadnt 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 wouldnt prefer it to her pussy, but there was something to say about the different sensations.

Jessies 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 cocks plundering her ass for a couple minutes but eventually rested my head on the pillow and just let the feelings take over.

Jessies husband let me fuck his wifes ass for four or five minutes until he invited himself on the bed with us. He stood up between my and Jessies legs as we all awaited the real fun. It was time for the main entré,e: 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 couldnt believe it was actually happening here. My heart started to pound again as I watched Jessies husband kneel down in front of us and, holding himself up by one arm, guide his cock into Jessies 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 Jessies husbands cock slid up against mine on the other side of the membrane that separated Jessies 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, Jessies cry being the loudest. I sank my nails into Jessies hips as I remained still in her ass for just a moment longer. I looked up with delight at Jessies legs, outstretched over her husbands shoulders, the heels of her shoes pointing toward the ceiling. Just like last time, there was so much sexiness to take in that it wasnt 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 husbands 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 Jessies 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 Jessies back was pressed close against my chest and stomach. As I was still getting the hang of my predicament, Jessies husband went to work, pulling his hips back and then slowly sinking his cock back into Jessies pussy.

I wouldnt say double penetration is like riding a bike, especially since we werent very seasoned in it, but it didnt take long at all to get into the rhythm we had worked out last time. Whenever I felt the cock in Jessies pussy slide into her, I pulled back in her ass. Then Id wait until I felt Jessies husband start to retract before Id 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 husbands 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 Jessies 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 Jessies body pressed close, pinned against me by her husbands 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 Jessies 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 Jessies husbands current position was my decided favorite for myself in a threesome, I did enjoy the view of Jessies legs in the air from this perspective, something you miss out on when youre on top.

Eventually, the audio was more than just heavy breathing. I dont 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.

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

Being on the bottom, I couldnt really dictate the flow of events. After several minutes of blissful group sex, Jessies husband slowed to a quick stop and pulled out. Jessies legs collapsed as her husband withdrew, and I ceased from banging her ass after three or four more hard pumps. Then Jessies 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 Jessies pussy. Again, Id be going into her first.

As Jessie sank down on top of me, taking my whole shaft into her pussy, Jessies husband suggested I go in her ass. I didnt really make sense to me if we were going to double-penetrate her again, and I was long overdue to fuck Jessies pussy anyway, so, honestly, I just ignored him. Instead, I briefly squeezed Jessies 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 Jessies 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 Jessies 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 Jessies husband hop back onto the bed and spread Jessies ass, drawing his cock near, I supposed it was good either way.

I slid my hands to Jessies shoulders while Jessies husband put both hands on his wifes 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 Jessies 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. Jessies husband and I slid in and out of Jessies 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 Jessies holes for what I wish had been forever. As I pumped in and out of Jessies 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, Jessies husband pulled out of his wifes ass, and Jessie hopped off me and then off the bed. I didnt 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 Jessies 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 wouldnt 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 mans cum on her face. At last, he pulled out and came all over Jessies 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 devils threesome was going on in that room, I dont know. I didnt 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 didnt come with her. She came up with one of her brothers, actually, but this account isnt going where you might think its going. The extent of her brothers involvement ends there.

Of course, due to the absence of Jessies husband, I never expected any action this weekend. She did ask me to keep Sunday open though so we could hang out, but I didnt 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 wasnt 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, Its not what it looks like. See you then.

I still wasnt close with Jessies husband, so I didnt 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, Id 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 didnt know what I was getting into. Jessie said it wasnt what I would suspect, but I couldnt imagine sex wasnt involved.

Room 201 was the unit to which I was directed to go. I cant 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 wasnt worried about getting stabbed — catching something, maybe.

As I headed up the stairs, I looked for Jessies 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. Ive 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 Jessies 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 well refer to him, but not only was I in shock, but this guy hadnt been good for Jessie when they dated, and I didnt 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 wasnt 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 hadnt 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 Jessies 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 shed 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 strangers house with Jessies husband two Christmases ago before my first threesome. At this point, I knew literally nothing about Andrew anymore and didnt 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 Jessies 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 Id 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 didnt last long.

The opening door revealed Ben. I hadnt 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 hadnt 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 wasnt 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, shed 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 shed gotten only three tells me she either didnt try hard enough or put a limit on it. Personally, having seen first hand what Jessie was already capable of, Im sure she could have taken another man or two.

I didnt even complain about Bens presence, not because I didnt want to but because there was no point. Beside, by now I was in with no turning back. If Ben wasnt 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 wont even waste space here with the stuff he was saying. I dont even care if he sees this writing. Lets 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 didnt 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 wasnt even aroused anymore, so its 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.

Jessies appearance was the only thing better than the fact that Ben finally went quiet. I cant 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 shed given birth once. Obviously Id 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 Id personally never dared to entertain.

Before we did anything, Jessie demanded we turn in our cell phones. Since wed all be getting chances to observe while not participating, Jessie didnt 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 Jessies thong strap aside and used the other hand to guide his cock against Jessies pussy. He didnt 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 wasnt 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 Bens 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 couldnt 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 Jessies 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 elses 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 Jessies 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 Jessies thong down her legs, not wanting to contend with the article at all. Now I could see that Jessies 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 Jessies ankles for now. It looked good with her sexy high heels.

My hands shook as I still adjusted to what was going on. Id never fucked a girl with others watching and, while group sex wasnt 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 wasnt just giving me sex but also performing for two other guys. As my erection protruded straight out, longing for Jessies 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 Jessies bare back as my other hand wedged the tip of my cock into her opening.

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 didnt really care who was watching or how many. Jessies 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 Jessies 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 Jessies 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 Jessies face.

It was my turn. I couldnt help but admire Jessies cum bespattered face, even though it was another mans 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 wasnt long until I felt my balls tighten. Intensely turned on, I whispered into Jessies ear if she wanted a double penetration. Maybe later, she gasped. A moment ago, I dont 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 Jessies 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. Were 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 wasnt 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 Bens inappropriate comments. It turns out, the silence didnt really bother me, and Bens 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 hadnt 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 ones 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, Ill 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 Id double-penetrated Jessie before, based on her comment to me a minute earlier. I answered that Id done it with her twice now. I think I earned his instant respect if I didnt 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 Jessies 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. Bens hands moved up to Jessies 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 cant even describe how hot she looked, and that sight wasnt even the best thing Id see that day.

Wildly turned on and without hesitation, I climbed between Jessies legs, hovering over her and not giving a damn if my legs accidentally made contact with Bens. After youve 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 Jessies pussy, which was tight still even after being ravaged earlier. Once the first inch was in, I put a hand on each of Jessies 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 Bens 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, Jessies 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 Bens cock in her ass and held herself up by her arms.

Ben took a minute to adjust to Jessies 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 Jessies 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 Jessies 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 Bens chest, my head over her left shoulder. Ben kept his head over Jessies other shoulder, and now we had Jessie firmly secured as the meat in our sandwich.

I put one hand on Jessies shoulder, not far from Bens head. My right arm slid under the a 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 devils 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 didnt weird me out at all anymore.

It took us a couple minutes to angle our hips right and get used to thrusting into Jessies 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 Jessies 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 Jessies 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 Jessies 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 Bens 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 Bens hands, and she threw one arm over my shoulder as she looked at Andrew and told him to get over here. Its not like he didnt 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 Jessies ass, only picking up his pace once I freed up the hole next to it. When I got off the bed, Ben grabbed Jessies 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 Jessies 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 Andrews 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 Jessies 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 Jessies holes. I had to refrain from touching myself for a little while so I wouldnt 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 didnt 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 Bens face, as she spread herself out and let both men have sex with her simultaneously.

Jessie lowered her legs under Andrews 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 Andrews thrusts. The boys sawed in and out of my beautiful friend, whose legs bounced in rhythm with the mens 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 couldnt 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. Its not like I was going to complain though: I had front-row seats to the hottest, albeit most degenerate, sight Id 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 Jessies twat before putting his hands on her shoulders and letting her sink down on him. Just as Jessies clit reached Bens balls, Andrews cock was already pushing to the hilt inside Jessies 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 Jessies 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 Jessies holes. Without warning, I got up and headed to the bed.

There wasnt really a way to carry out this idea comfortably. Id inevitably be in close proximity to both Ben and Andrew, but I just couldnt pass up this chance. While the other guys continued to roughly pound the squirming female, I stood beside the bed, next Jessies head — and Bens head — and offered Jessie my cock.

I looked down steadfastly at Jessies 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 Jessies 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 Jessies 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, Id look as far down as her feet in those high heels, which bounced slightly on either side of the other mens 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 Jessies 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 Jessies 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 Id had one orgasm already, this one wasnt as impressive, but I was still surprised at how much cum Id 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 Jessies pussy. Most likely Bens orgasm on one side of the membrane pushed Andrew over the edge on the other side, and both boys were cumming inside Jessies 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.

Everyone was pretty worn out by this point, but none more than Jessie. Cum leaked from Jessies holes as first Andrew and then Ben withdrew from her and the mass of human flesh disassembled. As I backed away and started to pick up my clothes, that guilt plagued my mind that maybe we had gone too far, but I quickly suppressed it.

We guys got dressed and did a little cleaning and freshening up while Jessie had rolled over in the bed, breathing heavily as she appeared to doze off. Her hair was untidily spread over the pillow, her limbs weakly lying on the blankets. Her body gleamed in the dim light from being coated in sweat, both hers and ours. My heart went out to my friend. She looked incredibly sexy lying there in only her high heels, having probably bit off more than she could chew. It took three strong men, but this sex goddess may have met her match.

Ben and Andrew left once they were dressed. Andrew asked if I was going to stay with Jessie, which I affirmed. Those moments were pretty awkward, but I was able to be comfortable and reflect on what had just transpired once the other guys left. The temptation to take a picture of Jessie as she lay there soaked in sweat and half-conscious at best was excruciating, but I didnt want to violate her trust.

About 45 minutes after the other boys left, Jessie finally sat up. Upon seeing me, she smiled sweetly and asked if I had had fun. She didnt complain of any discomfort, but I could only imagine she felt wrecked, both physically and mentally. I let her shower and change into some shorts and a t-shirt, and then I showered as well before we decided to spend the evening together in that cheap room Jessie had rented for the night.

After the sun had gone down, things officially went too far. That night ended with that true culmination of 10 years of friendship and sexual frustration with Jessie as I finally had passionate, intimate sex with her. While we would end up coming clean with Jessies husband, who surprisingly didnt completely lose his cool, I probably wouldnt be joining their marital activities for a long time, if ever again, which was a shame. But the temptation to fuck her that night was simply too strong. Once it got dark, Jessie decided to spend the night, not needing to explain to anyone where she was because she was a grown woman. Eventually, being bored and tired, not to mention the factor of all the sexual activity in which wed been involved, it was inevitable that we got naked and made love.

It started with harmless hand stuff. Hand stuff became oral, and oral became Jessie on her back, under the covers, taking my cock over and over again in her pussy as I lay on top of her with her arms around me. We kissed and fucked intensely for at least 30 minutes, my cock raging despite being worked hard that day. When it was over, I was both as satisfied as Id ever been and ridden with guilt because Id fucked another mans wife without his consent, participation or even knowledge. However, while pressed against Jessie and stroking hard and fast into her twat with no one elses involvement for the first time, Id be lying if I said it was anything short of a divine experience.

When we were finished, we both had orgasms. I pulled out just in time to cum on her face one more time while she continued to lie on her back and started to catch her breath. Relaxed and content, we fell peacefully asleep, even in that sketchy motel, but when we awoke, we knew we had done wrong. We werent awkward with each other or anything, though. We agreed we had fun, both during the the gangbang and our intimate sex. We even didnt want to close the door on future threesomes with her husband, but with his trust violated and the lines blurred, we thought it better to just enjoy the memories, let things go back to normal and move on with our lives.

Since then, Ive grown content with the thought that my sexual exploits with Jessie are likely in the past. They were wild, hot, dirty and fun, and Id always have those memories. Now, though, I was free to move on, to open the door for experiences with girls who didnt live more than 500 miles away from me and who werent married. I soon realized that double penetration was not only still a possibility, but something I could experiment more with as I pursued sexual encounters.

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A Delicious Jessie Sandwich

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...

3 years ago
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A Delicious Jessie Sandwich1

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...

2 years ago
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THP JESSIE LISA AND ARON PART1

1.01 The House of Pleasure THP: 1.02 Jessie, Lisa, Aron: 1.03 Jessie, Lisa, Aron, HDTV Condition: 1.04 Mira, Jessie, Introduction: 1.05 Mira, Jessie, First Lesbian Orgasm: 1.06 Mira, Jessie, Jacuzzi: 1.07 Lisa, Aron, Hair Removal: 1.08 Lisa, Aron, Deepthroat: 1.09 Lisa, Aron, Sibling Mating: 1.01 The House of Pleasure THP: The House of Pleasure, THP, is a high end, sexual complex in the Center of Bangkok. It opened two years ago and has become a must layover for business...

4 years ago
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JAKOB JESSIE PART 6RAPE RETRIBUTION

Jakob, Jessie, and Sandy took a break for lunch on Sunday. They were covered in saliva, cum and pussy juice--sticky in most places. After showering together, Jakob fired up the grill while the girls made some burgers. Jessie brought them out to Jakob wearing absolutely nothing-her tan lines disappearing since she started sunbathing nude. Jakob admired her lean features accentuated by her large firm breasts that seemed more suited for a much heavier woman. He noticed her nipples were...

2 years ago
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Jessie The Tornado Ch 05

Again, I suggest reading the first four chapters before beginning this one. Also, I want to emphasize that if you are expecting a story with non-stop sex, then you will be disappointed. Jessie & the Tornado, Ch. 5 Distantly I heard someone saying, ‘Sam? Sam? Sam?’ then felt someone shaking my shoulder. I looked up, and realized I was still sitting outside Jessie’s hospital room, and that Janice had been trying to get my attention, before finally having to shake my shoulder. Jessie was...

4 years ago
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Jakob and Jessie Part 4

From the minute he’d gotten the Sheriff’s phone call Jakob had known what he had to do. It was like killing a rabid dog or the feral hogs that had threatened his father’s stock. It was either kill Howard Holmes or live their lives in fear—fear that he’d get out of prison and hunt them down to wreak his “revenge.” In the end he’d done what he had to. He had rescued Jessie, his wife of less than a day, from a certain death at the hands of her father. Jakob had carried Jessie, insisting she...

2 years ago
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Jessie Part 2

Jessie and I had a “normal” date Thursday night, dinner and a movie. When we left Emily with the her babysitter, Emily was disappointed that we were not taking her with us. Jessie had to remind her that the 3 of us were going to the zoo on Saturday. The movie was a romantic comedy which Jessie had picked. The movie was ok, however the plot was very predictable. At least I got to be with Jessie. I had my arm around her throughout the movie and we kissed a couple of times, however the theatre...

2 years ago
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THP JESSIE LISA AND ARON PART2

2.01 Sara, Jessie, Canine, Mounting Frame Preparation: 2.02 Sara, Jessie, Canine, Frame Deepthroat: 2.03 Sara, Jessie, Canine, The Mounting: 2.04 Aron, Extractor and Enhancer: 2.05 Aron, Jessie, Mother and Son Mating: 2.06 Lisa, Golden, Bedroom Services: 2.07 Aron, Creatures, Bedroom Services: 2.01 Sara, Jessie, Canine, Mounting Frame Preparation: Sara knew Jessie was ready and walked her toward the mounting frame. Without hesitating, Jessie entered the frame, kneeled down and...

4 years ago
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Watching Jessie part 9 breeding Amy

Watching Jessie (part 9)It was late Sunday night. I wanted to feel Jessie’s pussy on my cock. Tyson and Darin had just left. They had been fucking her for over eight hours almost nonstop. She had taken ten loads of cum. Her pussy was stretched out and overflowing cum. When I got in the bedroom Jessie was lying on the bed almost passed out. She had moved out of the pool of cum she had made on the edge of the bed. Another wet spot was growing from her pussy where she now lay. I stripped quickly...

4 years ago
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My Last Thought Was Jessie The Ending

My brother, Jessie and I had spent the entire week at home and pretty much naked. We had sex several times every day. I couldn’t help but be worried about our parents coming home. I didn’t know what to expect, because I was sure that my Dad knew what was going on, considering he caught Jessie and I in the pool house in the bed together wrapped in each others arms naked. “You are thinking about it again aren’t you?” Jessie was standing in the doorway of the living room. He was naked, but his...

Incest
4 years ago
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A Delicious Jessie Sandwich

Introduction: The following is an account of my long-awaited first sexual encounter with my friend Jessie, coming with a wild twist. Some details are exaggerated for the enjoyment of the reader, but the integrity remains. Also, in the same interest, preparatory and hygienic details were omitted. The shot glass shook in my hand as I endured the most awkward 10 minutes of my life. Ive never been a drinker, but the alcohol was needed tonight to calm my nerves as I sat across the glass coffee table...

2 years ago
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Mom and Uncle Jessie Their Story

I walked into the living room where mom had slunk down into the leather couch. She was worn out from hosting family members that only showed up once a year. Mom had changed into her night shirt and her 40 year old leathery legs jutted out from underneath the hem in tired fashion. I sat beside her and patted her on her bare knee."So, was Jessie everything you thought he would be?" Mom asked after I settled in beside her.I gave her a very peculiar look. I really did not know how to answer her....

Incest
2 years ago
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Watching Jessie bedroom camera part6

Watching Jessie(bedroom camera part 6)It was late Sunday afternoon when Jessie got back. Frank showed up a few minutes later. Frank told me to go to the office and pull some reports and email them to him. He would keep Jessie entertained. Apparently he had told Terry he was going to the office to do what I was now tasked with. I pulled up the bedroom camera on my phone as I drove to work. Frank and Jessie weren’t in the bedroom as of yet. At least I wouldn’t have that as a distraction as I...

3 years ago
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Jessie Hanks Outlaw Queen

Street and Smith's _New York Weekly_ is proud to present the latest addition to the amazing legend of Eerie, Arizona. Jessie Hanks -- Outlaw Queen By Nicholas Varrick As Told To Ellie Dauber and Chris Leeson (c) 2003 Chapter 1 -- "Riders in the Night" "One... Two... Three!" Jessie Hanks yelled, as she swung the saddle back and forth, then upward. This time, it worked. The heavy saddle went over the top of the tethered horse, settling unevenly on the blanket on its...

2 years ago
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Jessie and Emily The Hunters Second and Third

I was driving to my favorite grocery store to stock up on essentials. I saw a blur appear in my peripheral vision and woke up two days later in the hospital. I had a broken leg, a broken wrist and a concussion. A delivery truck had run a red light and broadsided my car. Luckily for me, a policeman was witness to the accident and had quickly gotten an ambulance on the scene. Even better for me was the four moving violations issued to the driver of the truck. The company had sent a...

Hardcore
3 years ago
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Jessie is pregnant Jessies revenge

(5th in a series)I had by now excepted the fact that my wife, (Jessie) was going to get or already was pregnant with my bosses (Frank) baby. I was partially to blame for encouraging her to fuck other guys but I didn’t expect her to take their semen. Not only was she letting Frank fill her with his semen but Jessie wanted to have Frank’s baby. Jessie’s once tight pussy was now always gapped open her pussy lips stretched and loose from taking Frank’s BBC almost daily and sometimes multiple times...

2 years ago
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Dance of a LifetimeChapter 116 Jessie Hits The Jackpot

"Hi, Soph!" Jess chirped. "Hello, Jessie," Sophia said, sitting down in the chair across from the couch. "Welcome home. Now, do you mind telling me why you're sitting in my fiancé's lap kissing him?" "I'm trying to get him into bed," she giggled. "Oh, that did not help," Warren moaned. Sophia's mind boggled. She was prepared to believe she had walked into something innocent-until Jessie said that. "You're trying to get Warren into bed," Sophia said. "What...

3 years ago
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A Jessie McClintock Story SUCCUBUS PART 1

Jessie looked coolly at the man sitting across from her. She didn’t like him. Not his silk shirt, not his slicked back hair, not his fake tan. Gino the strip club owner. He was a walking stereotype. Her thoughts drifted mournfully to the Glade plug in working overtime in her office to combat this douchebag’s aggressive use of Axe body spray. Then she thumbed through the bundle of cash he’d tossed in her lap. “Look, I need this done, and I’m told you’re the only person to talk to...

1 year ago
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A Jessie McClintock Story SUCCUBUS

“So ya gonna take the job or not?”Jessie looked coolly at the man sitting across from her.  She didn’t like him.  Not his silk shirt, not his slicked back hair, not his fake tan.  Gino the strip club owner.  He was a walking stereotype.  Her thoughts drifted mournfully to the Glade plug in working overtime in her office to combat this douchebag’s aggressive use of Axe body spray.  Then she thumbed through the bundle of cash he’d tossed in her lap.“Look, I need this done, and I’m told you’re the...

Supernatural
4 years ago
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My Last Thought Was Jessie The Homecoming

I hadn't been back in Florida for more than three days and I was already miserable.  I missed Jessie so bad.  It was like having a part of myself ripped away.  I wondered to myself how I had went this long without realizing how much I really loved him.  My mom had noticed my depression, but when she would ask me about it I refused to talk about it.  Part of me wanted to blame her, because she had left my father.  But when I would really sit down and think about it I knew that if she had stayed...

Incest
4 years ago
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Watching Jessie

My girlfriend Jessie is a very reserved person sexually. At 25 she has never been with another person sexually save for her prom night. We were dating for almost three months before we had sex for the first time. We had been dating for six months where this story begins. Jessie is 5’2” tall with large breasts for her size and a beautiful round ass. Jessie could get the attention of any man if she so desired.Instead Jessie tries to blend into the crowd. At least until last weekend Jessie had...

4 years ago
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The Softening of Jessie Part 10

Mom and grandma went upstairs to change out of their workout gear, as Jessie relaxed on the family room couch. That was quite the workout. He felt good about himself though. It had been a while since he did physical exercise, so it was nice to get back into a routine. The exercises themselves were far different from his usual lifting weights, but he enjoyed the cardio segments and the one which targeted the thighs and buttocks. Knock Knock Knock. Someone was at the door. Jessie was...

3 years ago
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Jessie and the TornadoChapter 4

When I woke up the next morning, the first thing I did was check my car. Jessie’s purse was gone. I noticed that her car was not in the driveway of her parent’s house, and one of her parent’s cars was also missing. I tried calling her cell phone over and over, but she never answered. I left a number of messages begging her to call. Now, all I could do was wait. Had she and her parents gone somewhere? Then why were two cars missing? I paced back and forth from one end of my house to the...

3 years ago
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Bent Over for Uncle Jessie

Mom's older brother, Jessie, was always a flirt and often thought he was God's gift to woman. He was always quite the womanizer and knew just how to work the scene, even given his advancing age. I could see this as he mingled with the large crowd of family on our huge deck at the family reunion mom had organized. I watched Uncle Jessie flow through the crowd of family eying female family members like they were just another woman. All of them smiled at him and he reveled in it. I just snickered...

Incest
3 years ago
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Jessie The Tornado Ch 01

If you are looking for a story filled with sex, then you are probably in the wrong place. I don’t write sex stories. I (hopefully) write interesting stories that contain sex. Someone once said that women need a reason to have sex, while men only need a place. Like most generalities, I think that is generally wrong. I think that people need to have a reason to have sex and that if they care for each other, then the love and sex will be even better. All the participants are at least 18. The...

2 years ago
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The Softening of Jessie Part 27

The two began heading out when Jessie realized that he did not have his wallet. "Hey Ashley, how the heck do I carry my wallet? There aren't any pockets in this dress." "Yep, most dresses and skirts don't have pockets," Ashley replied. "I have something that will help," Jessie's mom said. She left the room and came back a minute later with a small light peach colored purse. "Put your stuff in here and carry it along." "Cool. I could put some cool stuff in here," Jessie...

1 year ago
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Jessie Fan Fiction

Jessie gasped seeing that Ravi's manhood was over 6 inches.             “Wow Ravi how long is it now?” Jessie asked walked forward and dropping to her knees.             “7 inches,” Ravi moaned as he felt Jessie’s young mouth engulf his meat.  Luke walked over to Jessie and started to suck on her left breast as he inched and played with her right one. Jessie moaned out load as she started to deep throat Ravi's cock.             “My gosh Luke" Our nanny is giving me such a good...

3 years ago
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Jessie

Jessie gasped seeing that Ravi's manhood was over 6 inches. “Wow Ravi how long is it now?” Jessie asked walked forward and dropping to her knees. “7 inches,” Ravi moaned as he felt Jessie’s young mouth engulf his meat. Luke walked over to Jessie and started to suck on her left breast as he inched and played with her right one. Jessie moaned out load as she started to deep throat Ravi's cock. “My gosh Luke" Our nanny is giving me such a good blow! Jessie pulled...

2 years ago
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How I Helped My Friend Jessie To Increase Her Boobs Size Part 8211 2

Hi everyone, I am Continuing my story… I looked at the time it was quarter past one. I went near her Me: How is your Leg Pain? Jessie: Now I feel little better. Me: You want me to massage again? J: No, No Need it is fine now. Me: Ok, then you feeling sleepy? J: No, But I want to sleep now. Because tomorrow after reaching home, has to go to my aunt house with my mum. Me: Ok, If you want to sleep you can sleep on my lap. She thought for a while and looking around to see others. Me: No one is...

2 years ago
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The Spftening of Jessie Part 11

Amanda felt like Jessie had enough excitement for the day. After his emotional outburst when Jason saw him clad in his girl's workout outfit, the voice change, and the trip to the nail salon, she took him home to relax. Jessie was thrilled with the way his nails looked. To think that he was so egotistical about how well he painted nails haha. Those women really taught him a lesson or two. As he admired his strawberry shimmery nails he wondered why black was always his favorite color....

3 years ago
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The Softening of Jessie Part 9

Amanda crept into Jessie's room and reached over to turn off his alarm clock. "It's ok honey, go back to sleep...you're not going back to school until that infection goes down," she calmly explained to Jessie, who had woken up. He laid his head back down and drifted again off to sleep. Amanda eyed her son as he slept. He looked so peaceful, and dare she say happy? Although the idea of changing him into a female was extreme on all scales, she felt that this was the only solution to...

4 years ago
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Jessie Babes Story

Thanks to FrenziedMaiden for her help and friendship. Jessie is a delicious girl. She lives with just her dad and idolizes him. She is not a virgin, but her partners have never satisfied her. They have never met her expectations. This is a story about how Jessie finds herself and everything she wants. Jessie was 22 and she had to admit that she looked good. Her boobs were high and tight, not too large, but pert and perfect for her figure. Her ass was just fine too. All in all, Jessie was...

4 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...

3 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...

4 years ago
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Jessie The Tornado Ch 04

Again, I suggest reading the first three chapters before beginning this one. Also, I want to emphasize that if you are expecting a story with non-stop sex, then you will be disappointed. * When I woke up the next morning, the first thing I did was check my car. Jessie’s purse was gone. I had already noticed that her car was not in the driveway of her parent’s house, and one of her parent’s cars was also missing. I tried calling her cell phone over and over, but she never answered. I left a...

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...

3 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...

4 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...

3 years ago
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Dealing With JessieChapter 2

Jedd Clampett This is the second of a nine part story. Please read and comment on the content. Vote of you like. Here goes part two... Gary had always been her rock in tough times, her ever faithful husband, and the responsible father. Where had it all gone so wrong? He realized none of that mattered, not to her, not anymore. To her he wasn’t anything. He was like a spare part, something extra, a left over. Really, what could he offer; nothing now, nothing she couldn’t get from her...

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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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...

3 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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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...

4 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...

3 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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Jessie and the TornadoChapter 3

Two months earlier On a Tuesday in March, I began doing some work on the outside. There were three very large flower beds in the front yard that had become completely overgrown and filled with weeds, and one warm day in mid-March I put on a pair of gloves and started pulling all the weeds out. I was wearing an old pair of shorts and a t-shirt, along with an old pair of sneakers. I also had on my customary “USMC” cap I almost always wore if I wasn’t working. One of the things I was...

1 year ago
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The Softening of Jessie Part 36

"Hey, they have a cool log ride here if you guys feel like it," Ashley stated to the other three. "Oh, like the one at Knott's?" "Similar on a smaller scale." "Cool! Let's go." The four headed over to the water ride weaving through the mass of people at the park. As they made their way through the crowd Jessie found himself falling a little behind. He didn't want to get lost from the other three but he kept bumping into people and getting stuck in front of others. Jessie...

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...

3 years ago
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The Softening of Jessie Part 8

Jessie returned home just in time for dinner. Mom and Grandma were putting their finishing touches on the meal. Ahhh, he loved the smell of his mom's meat balls and spaghetti! 'Just in time,' he thought. "Hey all. Smells good!" Jessie exclaimed. "Oh hi dear. Have a seat...you're just in time," Amanda said as she placed a bowl of aromatic spaghetti in front of her sweet child. "We need to talk Jessie. It's about school." "Oh yeah, I promise I haven't started any more trouble mom,"...

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