The sun hung high and unobscured in the cool and clear autumn sky. Two professional football teams were making preparations for week six of the National Football League's season while I fought my way through masses of cars, pedestrians and traffic cones. I'd actually never been to a football game, and that streak would continue despite the fact that I was trying to get to the stadium on game day as quickly as I could.
Beside me in the passenger seat was my fun and lovely friend Jessie. Almost two years had passed since her and my first true sexual encounter, which had been a threesome in which Jessie had been caught in between her husband and me. Since then, our sessions had been few and far between, though she and I thoroughly enjoyed them. We realized we had to get creative in order to make the most of our opportunities.
We finally made it into the tailgate party and began the daunting task of searching for an RV that could be identified by only a picture that had been emailed to me by a man I'd never actually met yet. I probably would have missed the vehicle entirely had that man not quickly identified Jessie and greeted us. Not only was he fairly well acquainted with Jessie's appearance due to the number of pictures of her I'd sent him, but Jessie kind of stuck out even in her jacket because not many girls wear silver stripper heels to a tailgate.
Tom and I had met online as a result of Jessie and my idea to maximize our exploits. Several weeks ago, Jessie had made arrangements to visit home, travelling the 500 or so miles that separated us ever since she and her young family had moved away, which occurred not long before our aforementioned first threesome. Because of work, Jessie's husband could not make the trip, so my female friend would be alone.
It wasn't the first time Jessie had come up alone. Her husband's job kept him at home down south often but still left him available to watch their toddler son. At first, those scenarios led to little more than just some time for Jessie and I to hang out. One fateful time, however, I banged Jessie without her husband's involvement, and it didn't take me long to get over the fact I'd committed adultery. We continued to shamelessly fuck whenever we had the chance, but, even still, something was missing from our twosome sessions.
Finally, just a month prior to this afternoon's event, Jessie, her husband and I enjoyed back-to-back days of sandwiching Jessie, and I knew it was the group element that had become almost a necessity in our sex life. As wild as any sex with Jessie had been and despite how unthinkable it had previously been to actually double-penetrate my hot friend-which has always been my most depraved fantasy-group sex was now something for which we were willing to push all the limits to attain.
"A Delicious Jessie Sandwich" was the name of the ad I posted on Craigslist. Jessie had suggested the website for me to seek out casual encounters when we had very briefly refrained from each other earlier this year. Though I'd yet to do so, now I was suggesting the site to seek out another guy who could take Jessie's husband's place in the threesome.
In the body of the article, I clearly lay out my inquiry: we wanted a relatively young and fit man to join me for heterosexual intercourse with my beautiful brunette friend who has been involved in group sex multiple times. Specifically, we were looking to double-penetrate her, preferably with me in her pussy while our new friend took her ass. I wasn't looking for endless emails, and we weren't willing to share nude pictures of Jessie, but regular pictures would be made available for those who were sincerely interested.
We had expected plenty of interest in our advertisement, but nothing could have prepared us for just how many emails flooded Jessie's inbox. I spent most of that first weekend on the couch in my living room just weeding through those messages, responding to whatever seemed legitimate and avoiding all the unwelcome dick pictures that came my way. What I ended up doing to help narrow it down was ask the guys what specifically they'd like to do and if they could host. With so many inquiries, I realized I could be picky.
Tom separated himself from the pack in his very first email: "What weekend is she coming up? I got a buddy coming into town to tailgate at the football game. Is she into airtight?" Tom could host, had a hot idea and even had an extra participant. I was sold immediately but wasn't sure if Jessie would be on board. I told Tom I'd get back to him.
Obviously, seeing as Tom was about to greet me there just outside the stadium on the weekend in question, Jessie had accepted - quite excitedly, by the way. As soon as Tom approached us, Jessie even leaned in to my ear and said she thought he was our guy. He wore sunglasses and a cap pulled down, covering his forehead as he made his way over to us. I noticed he was about my height but a little more built. His light brown goatee obscured even more of his face.
Once the slightly awkward introductions were complete, Tom led us into the RV he had supplied. He said he had spotted Jessie's face right away and that the high heels were a dead giveaway too, as I'd suspected. During our email conversation, Tom and I had agreed on Jessie's outfit, which included those shoes. I suggested them myself, actually, since, to date, Jessie had always worn a pair of sexy heels during our group sex episodes. Tom had agreed, saying heels added to the vixen factor.
Tom said he had half-expected us to not show up and also told me that he still hadn't told his buddy about this treat he had orchestrated. Even when his friend, whose name was John, met Jessie and me, he had no idea what was in store just yet. I noticed, though, how he eyeballed Jessie from head to toe, taking in the shoes, her bare legs and styled hair, which must have seemed out of place for what he thought to be a casual get-together with some new friends. Tom had wanted it to be a pleasant surprise for John, and it certainly would be.
John was a bit taller than I and a little overweight, but not much. He was clean-shaven and had dark black hair that peeked out from underneath his own ball cap. He may have known something was up when the slender, 5'5" lady took her jacket off, revealing her cheerleader outfit from college. It was a little tight on her, but, hey, she'd had a kid since then and was still rocking it, so it was easy to overlook. The uniform just so happened to be the same colors as the home team at this afternoon's game, but to protect identities, I'll leave those colors out. It was a little cool for Jessie to wear a skirt that went barely halfway down her thighs, a sleeveless top and open-toe shoes, but that RV wouldn't be chilly for long.
In addition, Jessie had curled her brown hair, which still hung down to her shoulders. Within her hair, she had tied matching little streamers to add to her team spirit. Finally, her finger- and toenails were appropriately colored as well. Jessie was far from a football fan in real life but was playing the part well this afternoon.
Naturally, John commented on Jessie's unexpected appearance and jokingly asked if she were an escort. Jessie blushed, the nerves starting to hit her (I knew they were hitting me, anyway), and responded by saying, "Oh, no. I don't charge." Then she flashed that bright white smile that was outlined by her deep red lips, a smile that almost always made me shudder from some type of arousal.
