Airtight Tailgate

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My fuck buddy makes new friends at the football game.
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dpingjessie
dpingjessie
1,144 Followers

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.

Meanwhile, Tom was getting some snacks and drinks together. The rest of us took seats in front of TV as we listened to the boring pregame show. Football is pretty cool, but I never wanted to listen to people I didn't know talk about what hadn't happened yet, especially not when I was anticipating the commencement of a wild three-on-one with my best friend as the centerpiece any minute now.

The pregame went to commercial, and Tom, who had taken off his cap and shades to reveal his green eyes and curled, sandy hair, caught my inadvertent gaze and nodded. He then revealed to his buddy how he'd made contact with us and for what we were really here. No, it wasn't football.

I muted the TV and stood up, bringing Jessie up with me as I took her by the hand. John was speechless at first but quickly conveyed both his approval and excitement. Our new friends asked Jessie to show us what she had to offer, motioning back to the couch seat from which she had just stood up. Jessie giggled, some nerves evident from the tone, and sat back down as I joined the two other guys in front of the TV. I'm sure Jessie didn't mind having the commercials blocked.

Jessie started the festivities by pulling up her top. She slid the garment up and stopped once it was just over her boobs, which were covered by a white lacy bra. Her grin grew wider as Tom and John voiced their approval of her B-cup breasts. They weren't huge but they were perfect for her frame, and my new friends found them as good as advertised even before Jessie had sufficiently disrobed.

After taking compliments, Jessie pulled the top off entirely and threw it beside the couch seat before throwing her hair back and fixing it. Then she leaned forward, showing off her cleavage as she reached behind her back to unclasp the bra. As her qualms left her, Jessie showed off an admirable comfort level for this type of situation. She wasn't a seasoned porn star by any means, but her confidence and shamelessness was evident, as would be mine. And, beside, the more I thought about it, she probably would make a pretty good porn star.

Tossing her bra toward us guys, Jessie laughed, played with her hair again and sat there, apparently waiting for orders. We guys were just taking in Jessie's rack, which hung free, no longer encumbered by the underwear. I felt pride well up inside me for being able to offer such a hot piece to these guys for an afternoon of crazy, debauched shit.

"What do you think?" I said to my new friends. "Will she do?"

"Oh, she'll do all right," said John, who was loosening his pants. Tom didn't say anything but followed his buddy's lead and started to undress. I decided to follow suit.

Over the past couple years, I had grown much more comfortable disrobing in front of other guys. In that moment, I remembered how difficult it was to just take my pants off the first time leading up to Jessie's husband and my double-teaming his wife, let alone carrying out the act. When it came down to it, Jessie was just too hot to pass up in such an act. Now, though, I had done enough threesomes with Jessie where I could just cut to the chase no matter how many guys were involved. After all, it wasn't any of them I'd be fucking, and nothing was more straight than giving this hottie in her late 20s the intense nailing she needed.

Amused, Jessie watched on as all three men stripped down in front of her. Once we were ready for her, Jessie slid off the seat and dropped to hands and knees. Then she crawled over the few feet to the three of us, who instinctually surrounded her in that RV. Without any words of instruction, we four assembled and prepared for a little pregame of our own.

I was so transfixed on Jessie that I didn't really notice that the other guys were even there, let alone that they were naked. I didn't even pay attention to the fact that they were as hard as I was until I watched Jessie take a cock in each hand and stroke it while she looked up at me with eyes that beckoned me to step closer. While she slowly beat off those strangers amid their moans, I came right up to her, cock in hand, and guided my erection to her mouth, which readily opened to accept me.

"Oh, fuck!" Tom said as he watched my friend suck on my cock while stroking two others, simultaneously pleasuring all three of us. "You weren't kidding about this chick!"

"You haven't seen anything yet," I said between pleasured sighs while Jessie's tongue pressed against the length of my shaft. From that point on, Jessie made her rounds, managing to give attention to each of as she alternated stroking and sucking us. Each of us guys would get a minute or two in her mouth before she would move onto the next guy - but not before taking the previous cock back in her hand to stroke it.

As the blowbang commenced, we all varied our pace and intensity. Sometimes Jessie would bob her head back and forth quickly, causing her hair to shake almost violently as she polished one of our knobs while rubbing her hands up and down the other cocks hard and fast. Other times, she moved slowly and seductively, licking the shaft from the base to its head while she gently stroked off the other two. Meanwhile, we guys alternated our response, doing anything from relaxing and letting the girl pleasure us at times and pulling her hair and thrusting deep into her mouth and everything in between.

Throughout, moans escaped all us men, while Jessie's movement on our flesh and her gasps added to the soundtrack. By the time we were ready to progress, at least 20 minutes had passed, and Jessie was already sweaty and out of breath. However, she was more than ready to go. My new friends didn't need to worry about my long-time friend's stamina.

We agreed to warm Jessie up before really giving it to her by simply taking turns with her on the couch seat. As she dutifully stood up, Jessie reached under her short skirt and pulled out her black thong, drawing a cheer from her male counterparts. She pushed the garment down to her knees and then turned around, shuffling over to the seat and kneeling down on it.

Tom and John deferred to me, but I wasn't quite psyched up enough yet to have sex with Jessie while other people watched. Not long from then, I'd be doing plenty of shameful things to her without a concern, but I'd need to watch her get fucked first if I were going to put on the same show. Therefore, Tom readily stepped up to go first, standing right behind Jessie's ass and reaching for the thong around her knees, which he began to pull off her.

No one had even noticed that the football game had begun. John and I just watched Tom remove the thong from Jessie's ankles and toss it with her top on the floor. He then wasted no time pushing his cock into Jessie's ready pussy, slowly but surely until he was deep inside her.

Jessie pressed her hands against the backrest and spread her legs a little wider as she moaned and took in that new cock. Tom cursed and put his hands under Jessie's skirt as he forced as much of his member into my brunette lover. Then he pulled back and began to screw her from behind.

"What do you think?" I asked Tom.

"She's fucking perfect, bro," he said confidently as he nailed Jessie harder and faster with each passing moment. Jessie laughed and squealed as the gangbang just got started. She knew she was in for a long afternoon, and I knew she was ready for it.

Watching Jessie get railed had me over the discomfort of being watched almost instantaneously. After just a minute, I was lined up behind Tom, ready for my turn. We agreed to give each other about five minutes with her in whatever position we desired before opening the afternoon up to the really depraved stuff.

I really enjoyed the view of Jessie with her eyes closed, open mouth moaning as she sank her hands into the back cushions and took Tom's pounding. I could have done without the sight of man ass, but it came with the territory, I guess. I waited my turn and then was amply ready to pick up where Tom would leave off.

As Tom slowed down to a stop inside Jessie, some loud cheers erupted. It was only then that we remembered that a game was going on, and I briefly looked over at the TV to see that the home team had just scored first. As soon as I noticed the game, I forgot about it and took my place in front of the couch seat as Tom stepped aside. I couldn't help but see that his cock was slick with Jessie's juices.

I decided to re-position Jessie, laying her on her back, parallel with the seat, her head on the armrest. Then I lifted her right leg as I hovered over her, resting her ankle on my left shoulder as I pushed my cock into her spread pussy. Jessie moaned and looked down, reaching to hold her twat open and help me guide my manhood into her warm, wet hole.

I hardly eased myself into Jessie, whose pussy was already primed, thanks to Tom's work. I slammed myself balls-deep into her immediately and then leaned over her as I started to fuck her hard and fast from the get-go. Jessie responded by laughing and grabbing my waist as I slid in and out of her tight, wet twat over and over again while Tom and John urged me on.

With both hands still on my waist, Jessie lifted her other leg onto my shoulder as well, so that both ankles were bouncing on my shoulders as I pummeled her pussy. John commented on how hot it looked to see this beautiful brunette get pounded with her legs up in the air, and I instantly desired to see the same thing. As I leaned over Jessie and looked into her beaming brown eyes while I fucked her, I brought myself as close to an orgasm as I could without actually going over the edge.

Rather abruptly, I pulled out of Jessie and asked John to start out exactly as I'd finished, with Jessie's legs on his shoulders. He obliged, and Jessie lifted her sexy legs back in the air while John got up on the seat with her and prepared for his turn in this round of sex. This time, Jessie dug her nails into the cushion beneath her as the larger man slid in between her legs and pushed his cock into her hole.

John was right: it was really hot to watch the hot brunette get fucked on her back while her legs rested on the dude's shoulders. Jessie grinned and clutched the seat throughout as John gave it to her hard, picking up speed as he went. As I watched this stranger have sex with my best friend, I thought I heard a groan outside, and, sure enough, I saw that the game looked to be tied up at 7. I couldn't have cared less.

After two or three minutes, John buried his cock to the hilt inside Jessie and pulled her up onto him. He then, still holding her tightly, leaned back and let down on the couch seat, Jessie now on top. Jessie giggled and put her hands on John's gut, her one leg resting on the cushion, while the other dangled down and touched the floor. Holding Jessie by her hips, John began to slide her up and down his cock.

Jessie took the lead from there and rode John for the next few minutes until this time was up. For a few moments, she looked right at me as her hair and boobs bounced along with her body as she slid up and down the hard shaft over and over again. The streamers in her hair rustled as well, reminding me of the cheerleader role play. Of course, she donned the skirt as well, which draped around her thighs and John's stomach each time she came down on his cock.

Moans and groans came from John, who was enjoying the surprise of his life, until Jessie ground to a halt, leaned over and informed John that his time was up. Without resistance, John let go of girl, who stepped off and moved away from the couch. She was giggling a bit and sweating as she caught her breath a little. She was plenty warmed up at this point, now, for the real fun to begin.

First, however, we graciously allowed her to clean up a bit in the bathroom. As Jessie took a few minutes, John and Tom sat down naked and watched some of the game. The home team was now down by 10 about halfway through the second quarter, but, again, I couldn't bother to care. Honestly, I was surprised that these guys could pay attention to football when we were all preparing to fuck a babe simultaneously. Then again, I remembered how uneasy I was the first time in group sex and figured pretending to care about sports was better than dealing with forced, awkward conversation while our prize took her time getting ready.

dpingjessie
dpingjessie
1,144 Followers