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Twenty-Year High School Reunion With Kelly

"Kelly anxiously looked forward to what turned out to be a night to remember."

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Author's Notes

"Some of the folks at this reunion I have written about previously in "Other Men's First Time With Kelly" and "Graduation Night With Kelly.""

It was early August of 1998. A couple of months prior Kelly and I had received, and RSVP’d to, an invitation to our twentieth high school class reunion. We were both looking forward to the event, but Kelly especially. That night she was the sexiest and most beautiful she had ever been in her life. And everyone noticed.

Our class was huge, a byproduct of the baby boom, and graduated over three hundred. The class stoner and chief idiot as a joke ran for class president and, also as a joke, we elected him. The result was that our five and ten-year reunions were last-minute shit-shows held at a local red-neck bar with minimal participation, neither of which we bothered to attend. Some of the girls who still lived in town decided they wanted something nice for their twentieth and took on the job themselves.

We checked into the Hilton at three p.m. and Kelly spent from then until the six o’clock cocktail party showering, doing her makeup, and getting dressed. The day before she had taken a vacation day and went to the salon to have her hair and nails done. She went blonde again, but a darker shade than the platinum she had been a year prior. She also decided to get bangs for the first time. Her nail color, of course, was fuck-me red. That evening I had helped her with a home waxing kit. Pretty much everything from her belly button south was as smooth as glass.

Kelly doesn’t wear (or need) makeup on a daily basis, so it’s always a treat when she dials it up. That night she went full Hollywood-glam. She even added eyelash extensions. Her blue eyes were heavily outlined and the whole picture was one of sexy beauty. At five-feet-two with her long legs, she was simply stunning.

She hadn’t let me see her dress prior to then quite on purpose. She still wouldn’t as she went into the bathroom to put it on, just minutes before we were to be downstairs for the reunion. It was a little black dress, her favorite category. It was a mini-dress, probably seven or eight inches above her knees. The top was a halter with a deep-V front that plunged to her waist. The outside edges of the halter were right at her sides, so no side-boob exposure, but the cleavage was breath-taking. Probably a third of her boobs were exposed.

The dress had no back at all. From the backside, it looked like she was topless and wearing a skin-hugging short skirt over her little bubble butt. The part of the halter around the back of her neck was concealed by her shoulder-length hair. To bend she had to do the “bunny dip” to keep her boobs in and her butt covered.

Age and genes have always been gracious to Kelly’s huge breasts. At thirty-eight her 34F boobs had virtually no sag and were very full and round. As she often did, she wore a beautiful necklace that hung down to just about nipple level. This one was a silver pendant with a ruby jewel and an elaborate design engraved into the setting. You really did need to look at it closely to appreciate the necklace. So, no, men weren’t perverts for putting their faces in her cleavage. They were appreciating quality jewelry!

Kelly’s summer of tanning in the backyard had really paid off. She always wore a small thong which both kept her open rose tattoo on a white background and it highlighted just how tanned her skin really was. On her feet, Kelly wore a pair of black strappy sandals with four-inch stiletto heels. I’m not sure how she got her legs so shiny but they glistened like a new car. Taken in total, she was breathtaking!

While in high school Kelly really did all that she could to not draw attention to her body. She wore loose flannel shirts and bell-bottom jeans nearly every day. She also had her super-long hair in either a braid or pigtails. Away from school, on her own terms, she was a flirt and flaunted her assets. Many of her classmates spent four years with her and had no idea at all that she was such a knock-out.

Within minutes of our arrival at the cocktail party, there was a buzz throughout the room. After about fifteen minutes a school chum I’d not seen in twenty years approached. “Have you heard them gossiping? They think Kelly must be Shelby.” My face expressed my complete bewilderment. “You know. Playboy?”

You could have knocked me over with a feather. During her college years, Shelby, one of our classmates, had posed for a Playboy pictorial. It was one of their “Girls of…” spreads. It gained her notoriety because, unlike many girls of that age who had dreams, she actually was in Playboy. And all of her classmates got to see her boobs!

The buzz around the room was that Kelly had to be the girl who had been in Playboy. If I could bust with pride, I did right then. I would have said something to Kelly except that she was already working the room laughing and flirting away as guys drooled over her cleavage and bumped elbows behind her back.

It was just before the seven o’clock dinner when Shelby arrived. Another wow moment. The comment I heard most often was, “Rode hard and put away wet.” Shelby had not aged well. I’ll be kind and leave it at that. It started another wave of gossip which was basically disbelief that she, not Kelly, had been in Playboy.

The best news was that because of the large turnout (over 300 people were there) they were able to afford a live band. After three hours of drinking, eating, gabbing, and suffering through the program of the evening we were ready to get up and dance. The dancefloor was packed. Kelly was mostly with her squad of gals she hung with while in school. We danced as a group for a few songs.

With a gentle tap on my shoulder, I turned around to see Lori. Lori was the second pussy I had experienced in my life. Kelly and me and Lori and Don and their roommate Rod had engaged in a liquor and pot-enhanced orgy when we were sixteen. Lori and I had been together a couple of times after that but completely lost track of each other after graduation.

Lori was a little pixie and a devilish imp. Sure, twenty years is twenty years, but she barely looked different. We danced. Soon the crowd was dirty dancing. Lori was all over me, humping my leg, backing her ass into my groin. It worked. She had me hard as a rock and I loved it. I could see Kelly was being passed around and working her way from man to man doing the same thing as Lori: Rubbing them to make them hard.

The band took a break and Lori drug me to her table. We spent nearly the next hour talking to each other. The last I had known she broke up with Don while still in high school. She married some guy from work soon after graduation. She had her daughter five months later and a son eleven months after that. Within four years she was divorced. A couple of years after that she reconnected with Don and they got married. Another couple of years after that her folks moved to Florida and they decided to go along. Once there, Don bought a Harley and that had defined their lives for the past ten years. They went to several rallies a year and she fucked a number of different guys at each. “Don likes to share me,” she said.

She shared plenty of her stories, clearly intending to keep me stiff. I shared many about Kelly and me, especially Kelly’s working at, what she called, the Playboy mansion. Of course, it wasn’t, but the place was open workplace debauchery and I shared enough with Lori to keep her pussy dripping. I knew that because she and I would each occasionally check on the other. My hand would slip under her miniskirt, past her panties, and into her wet slit. It was nice knowing that she too was shaved. She was rubbing my hard cock through my suit pants.

I was so engrossed with Lori that I had no idea where Kelly was. She shared later that Alan, who was there as a recent divorcee, had been dancing with her. She had him hard as bone and he had his hands under her skirt so often as they danced that her twat was running like a river.

When the band stopped for its first break Alan led Kelly out of the ballroom and to the restrooms at the far end, closer to the closed off side of the ballroom that was unused that night. He took her by the hand right into the men’s room and went to the large handicap stall. Kelly had wanted to fuck Alan the night of our graduation party. She had her hand in his pants at the party but unfortunately, he lost his load right there on her hand. He had told Kelly this night that he owed her “a do-over” and Kelly agreed.

He unzipped and pulled out an all-American normal cock. Kelly squatted on her stilettos in front of him and gobbled him down her throat in one move. She held him still giving him a minute to adjust, as she hoped he would. Once she was convinced that he wouldn’t cum on the first lick she bobbed up and down on his dick as he gently held her head. After a couple of minutes, his hands took hers and tugged her up to stand. Kelly took the hint, stood up, turned, and faced the side wall adopting the classic ‘being arrested’ stance.

Alan flipped up the bottom of her dress, found her thong and tugged it down to her knees. It took him just a moment to get his cock inside of her. Kelly held still as Alan did all of the thrusting.

Kelly thought to herself how pleased she was. She had been anxiously looking forward to this evening for weeks. Her pussy had been wet much of the summer and she had been fucking my eyeballs out. And there she was, with a cock in her twat already.

They had been fucking for less than a minute when the restroom door opened and two of their classmates came in chatting away, took a leak, washed up and left. Kelly had wanted Alan to be still while there were others in the room. He wouldn’t and fucked her the entire time, humping her even harder than he had been.

Kelly had done her best but as soon as the door shut she let out a too-loud, “Oh fuuuck!” and orgasmed. That excited Alan and he fucked her harder still. His hands had been on her hips. He moved them to her back and then inside her halter and around to the front until both hands were playing with her tits and rolling her nipples. Kelly came a second time.

Kelly could feel sweat dripping from Alan’s face and landing on her back. Both of his hands grabbed her tits too hard and he drove his cock into her so strongly that in one move she went from leaning against the wall to having her face and body smashed tight to the wall. “Fuck yeah, Baby! Feel me cum!” and he squirted his wad into her twat.

Alan pulled out fairly quickly and slumped against the opposite wall. Kelly backed up and sat down on the toilet and then released his load with a small splash. She had just started to pee when Alan insisted she let him watch. She could tell he wasn’t joking. She sat up straight and used both hands to spread her pussy lips wide open. She scooted further back on the seat to give him the best view. He leaned over to watch her piss out a full bladder. Kelly could see the big smile on his face. “Pervert,” she called him.

Kelly wiped and then slipped her thong into her clutch. Alan met her as she stood and planted his lips onto hers and they danced with their tongues. Someone else came into the restroom and entered the stall next to them. She and Alan left, with the “click, click, click” of Kelly’s heels leaving no question but what there was a woman leaving the men’s room.

Kelly found Lori and me on the dancefloor and joined us. I spoke directly into her ear and told her that Lori had kept me hard for the past hour or so (well, she was helped by the blue pills I had brought back from Mexico a few months earlier). Kelly gave Lori a high five for keeping my cock hard. Lori whispered to Kelly that we should all get together after the dance for a fuck. Kelly said, “Count me in! I’ve had one cock so far and I want more!”

Another hour must have flown by because the band announced they would take a break after the next song. They did a wild extended version of American Girl. Afterward, Kelly couldn’t believe I didn’t see the huge schlong on the lead singer. I told her it was because I didn’t look. In any case, Kelly assured me the guy had a bratwurst running down the leg of his leather pants. As the song was getting wilder and wilder a couple of the ladies quickly flashed their tits at the all-male band.

Lori was wearing a glittery tube top and mini skirt under a matching suit jacket. She took off her jacket and handed it to me. That was the first time I saw the huge tramp stamp on her back. Lori rushed to the front of the dancefloor and joined what was by then four or five gals that were doing quick boob-flashes to the band. Kelly must have had her back to it all since she was surprisingly late to the party. When she got up there it was probably a dozen women who had lifted, lowered, or opened their tops to show the band their tits.

The women’s eyes were all glued on the effect they were having on the lead singer. His cock had worked its way north and he had a huge hardon which, according to Kelly, looked like its head might pop out of his waistband. Being leather pants, he couldn’t help but have to use a hand to adjust himself as his cock hardened. The ladies were screaming in wanton passion. Several, Kelly among them, were grabbing their tits and squeezing their nipples at him.

A ‘wolf pack’ of men had descended on the front row flashers and were humping them from the backside and grabbing their boobs where they could. The singer stepped to the front of the stage to deliver his final wail of the song. Shelby was right in front of him and reached out and stroked his huge cock through the thin leather of his pants. The women were panting even harder. The song ended with sudden darkness and hearts, pussies and cocks pounding.

Kelly reached behind her and grabbed at what had been humping her ass: A nice big cock inside a pair of trousers. She stroked it until he spun her around and lunged in for a kiss. Kelly’s dress was still pulled to the side with one of her tits still exposed. He moved down and sucked her nipple as she bopped him on the head as she put “the girls” away.

“God, you are so fucking sexy,” he moaned.

Kelly again grabbed for his cock as he held her tight to himself. “Do you know how to use this?” she asked.

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“Fuck yes! Follow me.”

Kelly followed him out of the ballroom, across a foyer, into an elevator, and into a guest room on the sixth floor. “This has to be quick. I need to find my husband,” she told him. None of that was true but Kelly realized she had put herself in a potentially unsafe situation.

“No problem. I need to find my wife.”

Kelly breathed a quiet sigh of relief. She was lying on her back and pulled her dress up to her waist. He let his pants drop to the floor, waddled to the edge of the bed and mounted her missionary style. Kelly appreciated his cock. It was both longer and fatter than my standard-issue white boy cock. He was clearly fucking for just himself and managed to cum within a couple of minutes. Kelly enjoyed his cock although she did not cum.

He was smashed on her until she pushed him to get up. He stood and pulled up his pants. Kelly sat up, knowing she was draining his cum onto their bedspread. Once he was together she stood, grinned at the wet spot she had left for his wife and then they slipped back into the ballroom through separate doors. Kelly had no idea who he was so assumed he was married to a classmate.

Don had finally had enough catching up with his old baseball team chums and had joined Lori and me at the table. I barely recognized him. He put on a few pounds and had a huge full beard. I was surprised to see the streaks of gray in both his beard and his hair as Don was only forty.

Kelly soon found us and we all danced a couple of songs. Don was dancing with Kelly and asked if she would like to go upstairs to fuck. “I’d love another round,” she said which left Don a bit perplexed. We all left and headed to their fourth-floor room.

Kelly quickly announced that she needed a two-minute shower after all of her dancing. She ducked into their bathroom and Lori followed her a minute later. Don and I got caught up, mostly on their motorcycle rally experiences. Don was really proud to tell sex stories about Lori and men that he had shared her with.

We could hear laughing and giggling coming from the bathroom. Soon Kelly and Lori came out naked and barely dry. Lori pushed Kelly back onto the bed and then slowly crawled toward her pussy. “I wanted to eat you out in high school, but I thought it would have freaked you out.”

“Too bad you didn’t try. I would have let you. I had to wait another year for my first pussy.” By then Lori had her tongue shoved as far into Kelly’s vagina as it could reach. I got up and kneeled behind Lori and worked my prick into her still-tight-after-all-those-years slit. I reached around and played with her little A-cup tits and rolled her now-larger-after-children nipples. Don leaned over Kelly offering his cock to her mouth.

Don was perpendicular to Kelly and she was flat on her back. He started literally bucking up and down fucking her mouth hole. Lori knew how to eat pussy and soon had Kelly trying to scream out an orgasm. She had shared stories with me that even though the Harley boys loved to fuck her, what they all really wanted to see was Lori and another woman really going at. No pretend shit, just hardcore pussy eating with ass-bucking orgasms. I could appreciate their taste!

Don was the first to get up. He went to the window and opened all of the shades. Then he moved a lamp and a chair away from the windows and then turned on all of the lamps in the room. The rest of us had slowed our roll, just kind of watching him.

He reached for Kelly and pulled her off of Lori’s tongue. He stood her in the large window and mounted her from behind. He was grunting away as he fucked her. He pressed her closer to the glass so that her tits were smashed against the window.

Outside was a six-lane major highway. It was only a hundred or so feet away from us. It was elevated for bridges and their room was clearly in view of drivers. I heard the first honk. Lori pulled away from me and went to the window. I followed. At six-feet-four, Lori and I did not have the natural size matchup of Don and Kelly. Plus, Lori’s tight little clam was much harder to crack open from that angle. Eventually, though I got back inside of her. Lori also had her little boobs mashed against the glass.

The honks were only every couple of minutes or so. But, there were enough of them that it was pretty convincing that they could see us clearly. Kelly came hard. Don was really busting his hump slamming her twat with his dick. As she was screaming, “Oh fuuuck!” Don grunted loudly and rutted his cock as deeply as he could get into her. He left her his gift of cum. He stepped back extricating himself a minute later. Kelly let his load fall to the carpet.

I grabbed skinny little Lori by the hips and lifted her off the ground. She wrapped her ankles around the back of my knees as I continued to fuck her from behind. She started an entire series of “oh yes"'s that got louder and louder. The louder she got the harder I pummeled her hairless little beaver with my cock. Finally, she screamed her final, “OH YES!” and then went limp on me. I damn near fell over trying to catch her.

I was able to hold her and slowly lower her to the floor. She was half out of it, twitching from her massive orgasm. She had basically gone limp just as I was about to cum. My cock was bouncing hard. I was going to cum. The only question was where. I leaned over her little body and pushed my cock past her lips and started to hump as soon as I felt the warmth of her tongue. I pumped and pumped my load out of my balls.

Lori had worked me to a near-boil all evening. She paid the price through a huge load of my cum. She sat up gagging and snorting. It took her a few minutes to work through it but she finally got my load down her throat and was breathing again. “God Damn! I totally forgot how much you cum. I nearly drowned!”

Don had pulled Kelly over to the bed and she was sucking his limp cock. I carried Lori to the bed, laid her down and started licking her at her ankles and worked my way into her slit. It took Kelly fifteen minutes or so but she got Don hard and he gifted her with a small load in her mouth. It took me a bit longer to eat Lori to an orgasm but once she came I mounted her doggy style and fucked myself to a second orgasm. I have to admit her tight little clam was a joy to experience!

Kelly and I got dressed and said good-bye and headed toward our room. We had to walk past a balcony overlooking the atrium and lobby bar. We could tell that a bunch of our classmates were at the bar so we decided to head back down for a nightcap. Kelly snuck into the first restroom we came across to fix her makeup and then joined me standing at the end of the bar.

Soon, Terry, a jock that I had been decent friends with came up to buy a round and invited Kelly and me to join him. He was with a couple of buddies, sitting kind of behind the bar in a secluded area with oversize chairs and a sofa. I sat in one of the chairs, Kelly sat between him and Paul on the sofa. Pretty soon Kelly was in a deep one-on-one conversation with Terry while I talked to the other guys.

I noticed Terry kind of scooped up Kelly and sat her on his lap. Kelly’s back was to the rest of us. According to Kelly later, Terry slipped his hand under her dress as soon as she was on his lap. She laid her head on his shoulder and his fingers played with her pussy and her clit. He was shocked at first to discover she was panty-less but adapted quickly!

Paul couldn’t help himself. He slid across the couch toward Kelly’s back and was rubbing her naked back. Their other buddy decided it was getting too hot and time for him to scat. Off he went. Soon Paul’s hands were moving under Kelly’s halter and playing with her boobs.

Terry focused on Kelly’s clit and he got her off. She thanked him with an open mouth kiss followed by tongue hockey. Kelly could feel his boner poking her in the butt. Terry was liquored up and getting lathered up. “Oh man, I so want to fuck you…”

After a few more minutes of all three of them heading for a boil, Kelly breathed in Terry’s ear. “My pussy is right there. Get out your cock and stick it in.”

His face asked if she was serious? He got his answer. Kelly lifted up a bit as Terry unzipped. As soon as he pulled his dick from his slacks he was right in her slit. Kelly lowered her cunt and her full weight on him and sat there.

Terry started to twitch a little bit. Kelly pressed her steaming hot and wet pussy down on his cock. Terry twitched a few more times and then he erupted. Kelly quickly kissed him on the mouth to keep him quiet as he came. They kissed for another five minutes or so. When they broke apart Terry’s cock has shrunk to original size and Kelly had left his load on his lap. They had been so subtle and moved so little, that I honestly had no idea they had actually fucked.

Paul had been rubbing her back the entire time. Kelly climbed off Terry and turned to him, kneeling on the couch between him and Terry. “What would you like, Paul?”

“I’d like you to sit on my lap too.” He said with a huge grin. Kelly placed one knee over his lap and sat on her knees straddling his legs facing him. Paul moved in to kiss her. As they kissed he unzipped his fly. Kelly fished out his cock and held it in place as she lowered her pussy onto him. Paul’s dick was kind of small but at that point, it was a cock and Kelly was on cloud nine having another cock in her.

A bar server surprised me and asked if I needed a drink. I ordered another beer and sent her on her way. She gave Paul and Kelly an odd look and assumed they were just being passionate. Kelly’s dress hid what was actually going on. Almost as soon as the server left, Paul pulled one side of Kelly’s halter top open and was sucking on a nipple. I could see his ass was rhythmically moving up and down on the couch. Not a lot, but noticeable if you were watching as closely as I was. I noticed a couple of bounces went higher than the others.

Just before my beer showed up, Kelly slid back toward his knees and Paul tucked his cock away. Soon it was bar-time. We all gave a toast to Kelly and clanked our beer bottles. No long after all four of us stood to say goodnight. Terry and Paul both hugged and groped Kelly one last time. They were locals so they drove home. Terry had started to walk away when he stopped and turned around. “Were you really in Playboy?”

“What do you believe?”

“I believe you were.”

Kelly winked at him and blew him a kiss.

On the elevator, to our room, there were two other couples in front of us facing the door. Kelly lifted her dress to show me the cum trails she had running down her thighs. I had swallowed another blue pill when had gone back downstairs and hung out with Terry and Paul. It was working. I had a penis-tent in my slacks.

Kelly stepped into the bathroom to pee and clean off some cum. I stripped naked, peeled back the covers and was lying naked on the bed with a hard prick aiming toward the sky when Kelly joined me.

She climbed aboard and sat upright slowly riding my cock. We gave each other a complete debrief of our evening. A couple of times Kelly ground her pussy deep onto my cock as I told her some good stuff that Lori has shared. She had a couple of small orgasms on me. After we were all caught up, and struggling to stay awake (it was after three a.m. by then), I rolled Kelly over to her back and fucked the hell out of her. I was really pounding her pussy into the mattress.

Working on a third orgasm of the night wasn’t easy. Kelly’s twat paid the price. I don’t think she minded though and she screamed through an orgasm that I thought would for sure bring hotel security to our door. Finally, I felt that good feeling in my balls and I had an orgasm. I was only able to give her a tiny load, but I had gotten off. With that, I rolled over and fell asleep.

It was close to ten a.m. when I woke up. My cock was so hard it ached. I assumed it had deflated when I fell asleep, but I can’t say that I knew that for a fact. In any case, I needed to fuck, cum and see if that would make it go down.

Kelly was sleeping face down with one knee bent. The covers were still off the bed. ‘Perfect!’ I thought to myself. I rolled over and hovered over her straight leg. With a little aiming, I hit her vagina on the first try. Once I was inside I fucked away.

Kelly woke up of course but was still pretty groggy and pretended she was asleep. I figured as much and greatly enjoyed the game nonetheless. I fucked her hard for a solid ten minutes. At one point she very subtly bit her pillow. I felt a small flow of her cum on my balls.

The game was ridiculous as I was shaking the hell out of both her and the bed. But Kelly played it as straight as a cadaver. I was never so happy to feel an orgasm arrive. Apparently, seven hours was enough to fully reload. I blasted her cunt with a signature huge load and then rolled over exhausted.

I knew checkout time would arrive soon so I got up and took my shower. I was actually quite relieved when my cock deflated. When I pulled back the curtain to get out Kelly was sitting on the toilet. “Did you fuck me in my sleep? My pussy is full of cum and it tasted like yours.” God, she was fun to play with!

I was shocked when, almost an hour later, Kelly came out of the bathroom. She had done up the same full makeup as the previous evening. Don’t get me wrong, I loved it. It was just out of character. “What gives?” I asked.

“Hey, if they think you’re a Playboy model, you have to keep up appearances.” Kelly slipped on a nice pair of shorts and a fancy embellished T-shirt. I couldn’t help but notice that she had skipped wearing a bra.

We went downstairs for brunch. As soon as the too-cold air of the dining room hit her nipples they were on triple high-beams. There were perhaps twenty people from the reunion eating. All eyes in the dining room were on Kelly as she made her trips to the food stations set up for the brunch. She sashayed her ass as she walked back and forth and we both loved the attention she received.

Our four-hour drive home that Sunday was also a blast. Kelly had her shorts off for most of it as she and I took turns playing with her pussy.

 

 

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Written by GoodToBeMe
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