It was late afternoon, and Jessie and her husband were on their way from dropping off their son with Jessie's brother. As they took care of the kid, I checked into a Motel 6 that was just five minutes away from my apartment. I waited in the room for about 20 minutes before the two of them walked in together, Jessie smiling as she pulled off her long, heavy coat that not only kept her warm in the 10-degree weather but also covered up her outfit that would have been inappropriate for most occasions. I smiled back at her, already getting hard from just seeing her, knowing what was about to happen. Her husband and I, meanwhile, barely acknowledge each other.
As soon as Jessie's coat hit the floor, I was stunned. Her outfit may not have been quite as arousing as the Santa get-up she had sported last time, but her attire was very boner-educing regardless. She wore a tight, white halter top that almost covered her belly button to go with a dark gray pleated miniskirt that left little to the imagination. For shoes, she donned silver six-inch high heels that showed off her bright pink pedicured toenails, which matched her fingernails. Topping it all off, around her wrist and ankle were the same bracelets she'd worn last time, in addition to just the right amount of makeup on her face that was framed perfectly by her brown hair, which she had curled just slightly to curve around her cheeks and bend outward as it approached her shoulders.
Jessie walked straight to the queen size bed in the middle of the room and sat down on it. Meanwhile, her husband had the sense to turn the fan on all the way up to mask some of the noise that would be coming from our room. Even though it was just now turning dark outside, there was no way of knowing who would be around to hear our escapades, even through the cement walls. The first couple minutes were awkwardly silent, but Jessie broke the silence with a line that she had clearly rehearsed ahead of time and probably stolen from a porno.
"Do you know what my favorite cookie is?" Jessie began as she reached for the hem of the halter top. She immediately answered the question for us: "Oreo." She smiled wide across her face, holding in a giggle. Her voice cracked a little as she spoke, betraying her nerves. Also I'm not sure, but I think that reference more suitably depicts two black dudes with a white chick, and Jessie, being only slightly tan, was the darkest one in the room. Anyway, despite Jessie's lack of confidence in delivering, she said it well enough to turn me on just a little more than I'd already been. Even if her actual use of the line wasn't flawless, after this session, I'd always remember it as if it were.
Not hurting her attempt to be sexy was that she was pulling off her shirt as she sat on the edge of the motel bed. Unlike last time, there was no delay in Jessie's presentation. She had arrived to the motel already prepared, and we didn't feel the need to consume alcohol to push us on this time. I'm not sure I could have carried through the first time without those couple shots I took, even though I almost never drink. This time, though, with the sights and sounds of the Jessie sandwich her husband and I enjoyed more than 13 months ago forever etched into my brain, I had all the motivation I'd ever need.
The anticipation of what was about to happen was arguably greater than last time, being free from the anxiety and most of the awkwardness. While the thrill of doing it the first time held an element that could never be matched, the build up to this follow-up session was almost unbearable in the best way possible, now that it was finally occurring. Over the past 13 months, I wanted nothing more than to relive the blissful experience of double-penetrating my favorite friend of 10 years, and this time I knew exactly what to expect and had no fear of disappointment. Of course, it was still a little weird leading up to it, as I would probably never be completely comfortable around Jessie's husband - or, in the context of intercourse, any other man for that matter. However, those qualms very obviously didn't end up deterring me last time, and they most certainly would not hold me back this time, given my determination.
Double-penetrating Jessie had always been a fantasy of mine, but now that the fantasy had been fulfilled once, the burning desire to sandwich Jessie only grew. I had already been a little obsessed with her beforehand, but now that fixation bordered on desperation to do it again. On this freezing day in early February, I stood in that motel just moments away for abating that frustration. My heart was racing and my mouth was dry even before we undressed.
It was no surprise what was about to happen next as Jessie threw her top away, revealing a white frilly strapless bra. Interestingly enough, none of us in the room had actually once specifically mentioned that we were convening for a double penetration threesome. To this point, Jessie's Oreo reference came the closest to a definite allusion. After carrying out the debased act once, it was just a matter of saying where and when for the second time. The "what" was mutually understood.
We had all thoroughly enjoyed the raunchy, ungodly group sex last time and agreed immediately to do it again. However, different circumstances stalled the follow-up session. First of all, there was the initial awkwardness that comes with banging a girl in a devil's threesome after almost a decade of mostly platonic friendship. On my part, like I implied already, I never felt comfortable with Jessie's husband to begin with. Getting carried away with teaming up on his wife only complicated that issue, especially when I was forced to communicate with him over the months.
Naturally, I had no qualms with talking to Jessie about doing terrible things to her slender 5'5" frame and actually, over the months, often attempted to steer our conversation toward the subject, in part because it turned me on and in part because I hoped to expedite a fresh session. Unfortunately, Jessie was less eager to talk about it than I was. She insisted that she loved the experience and had no regrets, but her quickly dropping the subject made me suspect that she felt uncomfortable or dirty - even guilty.
After a couple months, Jessie finally did admit that she had felt a little awkward moving forward after such outrageous behavior, but she was telling me now that she had gotten over whatever guilt and shame there was. We started planning as early as March of last year, which was when Jessie communicated that she and her husband were ready to add a little excitement to their marriage again. It was just a matter of a time and a place.
Therein lay the reason for the delay. Almost a full year passed between Jessie's first text to me stating she was ready for another double penetration and this moment where she began to disrobe in a cheap motel as she not-so-confidently quoted porn. First, Jessie and I lived more than 500 miles apart, and sometimes that obstacle felt like the least of them. We both had good jobs and firmly rooted lives in other states, not to mention Jessie had a child. When she did visit, she always stayed with her parents, a situation that didn't present an opportunity for disgraceful sex. I, on the other hand, had two roommates at home and had no excusable reason to take off work and head hundreds of miles south to join a dude in banging his wife - though I started to consider it a few times. Most of the time, her husband just couldn't get off work. At least Jessie worked online from home, so her job was never an issue. Otherwise, we might still be waiting.
The stars had kind of aligned for us when Jessie's husband and I fucked Jessie in unison that first time. It wasn't until near the end of last year that we realized we needed to just make it happen, but even then, for one reason or another, the plans fell through. Either the couple couldn't make the trip or one of us couldn't find the time when Jessie and her husband were in town. This past January, we had everything in place, which is when we first settled on the motel idea, and then Jessie got very sick. Finally, in February, they made the excuse to visit for Jessie's mother's birthday.
