Her Brother And His Friends Have Sex With Kelly
- 3 years ago
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It was the spring of 2000. I had to attend a convention for work. The good news was that Kelly was invited along also. The meeting was at a very nice resort hotel, but honestly, they’re all pretty much alike. It doesn’t even matter what city they are held in.
You fly in, jump in a cab, are stuck in a hotel/convention center for a couple of days, jump in a cab and fly home. But being able to bring Kelly along meant I wouldn’t suffer from boredom!
Kelly attended the meals, guest speaker sessions, trade show, and finale banquet. She had several hours of downtime between some of that and was working on her tan in the California sun. The outdoor pool area was huge and very quiet. This wasn’t a meeting with young families and there weren’t all that many spouses either.
Kelly was tanning in a bikini which was respectable enough for the venue. But there is also a counterpoint that her 36G boobs in a bikini are borderline obscene no matter what! Kelly couldn’t help but notice a good-looking man swimming some laps and also hanging out in the sun. She guessed him to be in his fifties. He didn’t approach her but he definitely was working in an eyeful where ever he could.
Kelly joined me for the trade show. We wandered around collecting things I would leave behind in the hotel trash and making small talk with salespeople, half of whom were as bored as I was.
As we wandered down the aisles a sales guy stepped out and introduced himself and his product. He was actually a really nice guy and we chit-chatted for a while. I took his card, he said he'd call me to set up with something; blah, blah, blah.
As we were wandering the next aisle Kelly mentioned that Steve, the guy we had just met, had been down at the pool this morning.
“And?” I asked.
“Nothing much. I think he was checking me out. But, then I was checking him out too. He looks pretty good in a swimsuit.”
That evening we were at dinner. We were sitting with two other couples I’d never met. There were two open chairs next to Kelly when Steve walked up and asked if a seat was available.
We invited him to join us and he sat next to Kelly. He was born to be a sales guy. He kind of led the table conversation before dinner and had everyone laughing and interacting. He really had Kelly laughing pretty hard a few times.
During the dinner/presentation, I could see Steve was keeping up a private conversation with Kelly. Eventually, he asked if that was her that he saw by the pool earlier. Kelly said she was there and asked was that him swimming the laps?
Later in the conversation, Steve told her that she was very striking in a bikini and she should be very proud of her figure. I saw Kelly blush. She was keeping me up on their conversation but playing it all very low-key.
When it was clear to both of them that they were becoming fast, flirty, friends, he asked if they were real? Now Kelly has been asked that question many times in her life. It offends the shit out of her and guys tend to get punched.
But in that context, she wasn’t offended and said, “One hundred percent all me nothing enhanced.” She said it with a great deal of pride.
Steve replied, “Even more impressive!”
I should probably share how Kelly was dressed that evening. She was wearing a ‘little black dress’. This one came maybe two or three inches above her knees. The top was a halter with an open back. The top has some silvery beads sewn in here and there that made it shimmer in the light. It was a very light-weight material and swayed and moved as she walked.
On her feet, she had a pair of stiletto-heeled black sandals. Nails (top and bottom) were fuck-me red. Her hair those days was blond, straight, and hung to her shoulder blades. She also wore a beautiful and ornate necklace that hung in her cleavage.
The necklace was an old trick of Kelly’s that she has used countless times. If you hang a beautiful necklace between your huge tits pretty much anyone can notice and comment on the beautiful jewelry, while in reality taking a good long look at her cleavage.
With a backless halter, it was pretty clear she couldn’t wear a bra. She had also waxed before the trip and loved leaving the panties in the suitcase when she was dolled up.
So, no surprise that Steve was fixated on her boobs. As the dinner went along and the wine flowed they got flirtier in their conversation. They were discussing the shape of her nipples, the size of her areola, what made them hard, the fact they were hard right then. Panties; no she wasn’t wearing any, yes, she was getting quite wet.
I’ll give them credit; they kept up a pretty good front at the table. I’m pretty sure no one else suspected they were nearly verbally fucking each other during dinner.
My updates were less frequent but I clearly knew what they were up to when Kelly subtly adjusted her dress. She pulled up the back of the lower half so her ass was directly on the chair. Her twat was running and she didn’t want a wet spot on the back of her dress.
By the time the dinner was finished Kelly had a vivid description of Steve’s cock as well. She was assured that it was rock hard, but they were still trying to be cool so she took him at his word.
There was a break where folks hit the restrooms, left if they wanted (as did the other couples at our table), refreshed their drinks and the band got set up.
Kelly went to the restroom to freshen her makeup and blot up the river running from her pussy. Steve and I got in line for drinks.
“So, now you’ve ‘met’ Kelly,” I said.
“Yes, she is an amazing woman. You must be a very happy man!”
“Indeed I am. She is a very sexual being and really loves new experiences. It looks like she finds you very fascinating. It will be a fun and interesting night. Do you plan on hanging around for the entertainment?”
Steve said, “I think I would be a fool to leave.”
Our understanding was established. We were all on the same page. We met Kelly back at the table just as the band started up. Steve invited Kelly to the dancefloor.
They stayed out for several songs. On the last song, Steve twirled her pretty hard and her dress flew up. Anyone watching closely got a quick view of her bare ass.
When they returned to our table I could see Steve was trying his best to hide his hardon. We were the only ones at the table, which had a long tablecloth that hung nearly to the floor. Kelly had again pulled up the back of her dress as she sat down.
There were only a few people sitting at tables, mostly just folks taking a break from the dance floor. The ballroom was huge and there wasn’t anyone within fifty feet of us.
I moved closer to Kelly and asked if she was having fun? The look in her eyes said it all. She was on fire. I slid my hand under her dress.
Her slot was soaked. I easily slid three fingers into her twat. She moaned louder than she meant to. Steve immediately knew what I was doing. As I started to finger bang her, Steve put a hand under her dress and played with her clit. Kelly slid down in her chair which gave all of us a better angle for our assault.
It was within just a couple of minutes when Kelly covered her mouth with a hand as she orgasmed. Steve and I kept playing with her twat. Five minutes later she came again.
Kelly had reached into our laps and had a tight grip, through our suits, around a hard cock with each hand.
After she came a second time she quietly said, “Take me somewhere.”
We headed for the doors and across the large hall were doors to some outside grounds. I led us outside. We walked along a paved path and came to a park bench. There was no one else in sight. Kelly pushed Steve to sit on the bench. They both worked to quickly pull out his cock.
His dick was pretty much the exact same size as mine. Straight and about six inches.
The moment his dick was loose Kelly sat her wet cunt down on him and started to ride him. She pulled me to her face. I had my cock out and she sucked me into her mouth. Kelly came in seconds. She was so worked up from all of the flirting and us playing in her cunt, a good fuck wasn’t a want, it was a need.
As soon as that orgasm was out of the way Steve got into her rhythm and was fucking her hard. In another five minutes, Kelly had to spit out my cock as she came again. She was trying so hard to be quiet but anyone close would have heard her.
Just then, we saw a guy right there with us as he was walking down the path, apparently heading back to his hotel room. Kelly was bouncing on a cock; her halter top was pulled open with both of her huge tits bouncing away.
Steve and I had both been working on her nipples. I had my cock sticking out right next to her mouth waiting to be sucked back in.
“Oh shit! Guys, I am so sorry. I swear I didn’t see anything.”
We could tell his big head wanted him to just keep walking. His little head wouldn’t let him move past the sight of Kelly’s tits and her being fucked. He just sort of froze.
To make it even wilder, Steve orgasmed. He wasn’t really noisy, but he bounced her up pretty high and we heard him groan. Kelly reached for the guy’s slacks. He stepped closer and she could feel his half-hard cock through his slacks. She grabbed hold of it and he was hard in an instant. He was still kind of frozen.
“Pull it out,” I told him.
He quickly unzipped and it was out immediately. I think the dude was going commando? Kelly slid off of Steve and went to her knees sucking this guy.
I have to say, he had a nice-looking dick. Maybe an inch longer than Steve and me and a little bit thicker. This guy was a lot younger than us as well. I’m guessing around thirty?
Kelly didn’t want to stay on her knees. She went to the bench. Steve got up and Kelly laid on her back. She had her hand on the guy’s cock ever since he had pulled it out.
She pulled him to her and he instinctively got into her saddle and fucked her on the bench. I moved to her head and she again sucked on my cock.
This guy must have thought it was freaking Christmas. He was fucking her very ‘politely’ for lack of a better way to describe it.
Kelly popped me out and said, “Harder… harder… fucking harder!… that’s it… harder… oh, fuck… harder… oh fuck, oh fuck, OH FUCK!"
And Kelly had a huge orgasm. I saw it coming and shoved my hand over her mouth. She squirted all over that guy. His slacks were soaked. He started to slow up.
“Don’t stop. Cum in me. Fuck me hard. I want to feel you cum!”
In just a few strokes he locked up and blasted her cunt with his juice.
He slid out of her and tucked his cock away.
He looked at all of us and said, “That was fucking insane! You all have a great night!” and went on his way.
I gave Kelly a hand to get up from the bench. I slipped the halter top off her shoulders and she pulled her arms through. I positioned her so she was leaning on the arm of one end of the bench. I got behind her and flipped the bottom of her dress way up onto her back. Her dress was scrunched around her waist and she was as close as she could get to completely naked.
I aimed my cock at her hole and went in deep. The first twenty strokes or so I pulled all the way back out and emptied her vagina of two cum loads.
She pulled Steve over and used her mouth to clean off his cock. It took a little time but she got him hard again and kept sucking on him. I heard footsteps coming.
A couple of guys who were clearly tanked came upon us. They slowed way down and stared at Kelly’s body being fucked. They stared for maybe thirty seconds or so and kept on walking, not having said a word. Just seeing the looks on their faces got me to unload. Kelly’s body is almost overwhelming to the senses.
I pulled out and put my dick away. Kelly sat down on the bench and worked Steve’s cock with her hand.
She looked up into his eyes and said, “Cum on me. I want to watch you do it.”
Steve took over and jerked the hell out of his cock. It took a few minutes. He lurched forward towards her tits and laid a nice puddle of cum on one boob. Steve stepped back and put away his cock.
We both were enjoying the view of Kelly sitting there with her little dress looking like a belt. Her arms were stretched out wide on the top of the bench. Her knees were spread wide, with her hairless cunt on display.
It was the first time Steve noticed the rose tattoo on her pubic mound. He leaned down to take a closer look. He complimented her on the tattoo and asked if she had any others.
“No, that’s the only one,” She replied.
“Well, I’m damn glad I got to see it!” Steve made a very warm goodbye and thanked us both.
We were all flying out in the morning. He and I shook hands and he headed to his room.
I helped Kelly get out of her heels. She wanted to carry them. She pulled up the top of her dress but left one boob exposed, the one with Steve’s load running down it.
We walked along the path to the tower with our room. One guy walked past us on the path and did a double-take as he caught a glimpse of her exposed tit.
She left it out as we went to our room. It was a short walk to the elevator. No one joined us on the trip to the twenty-sixth floor. On the crazy long walk along the hallway to our room, one guy stepped out of his room with an ice bucket and just froze as we walked past. Kelly winked at him as she passed close by him.
Even at age forty, life with Kelly is as wild as it was at sixteen!
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Straight SexIt was February of 1993. Back in 1976, when Kelly was sixteen years old, she was at a party at a friend’s house that turned into an orgy and she was fucked by a half-dozen men that all worked together at the Ford dealership. A couple of them were double her age and one’s name was Gary. Fast-forward sixteen years and we had moved a couple of states away. Needing her Mustang repaired, Kelly went to the local Ford dealer the previous October. Lo and behold, Gary was the service writer.Her car...
ThreesomesIt was August of 1977. Kelly and I were going to be seniors when school started back up. But before then our little town had its annual summer festival celebrating our local crop. Kelly and I had made our first trip to Milwaukee’s Summerfest several weeks ago and we knew that nothing in our little town could compare to that experience. Kelly’s sexuality was beginning to boil. She had dressed like a slut at Summerfest and loved the attention and the sex that it had brought her.Even though her...
TeenIt was August of 1977. Kelly and I were going to be seniors when school started back up. But before then our little town had its annual summer festival celebrating our local crop. Kelly and I had made our first trip to Milwaukee’s Summerfest several weeks ago and we knew that nothing in our little town could compare to that experience. Kelly’s sexuality was beginning to boil. She had dressed like a slut at Summerfest and loved the attention and the sex that it had brought her.Even though her...
TeenIt was 1976. Kelly was sixteen and got her first job working in the bakery/deli at the local grocery store. As she was still in high school she worked a variety of shifts after school, evenings, and on weekends. The job supplied a hideous smock as their uniform. Kelly wore her own jeans and T-shirt under the smock. The smocks were also cleaned by the store. There was a small breakroom in the back area where folks could store their jacket, purse, whatever, and that was where they would put on...
ReluctanceIt was a Saturday late in the summer of 1991. Kelly had made plans to spend the day with her good friend Becca. Our sexy fun with Becca began in 1988 at our ten-year reunion when she jacked me off at the post-reunion pool party and then fucked me after I drove her drunk ass home. It continued the following summer when I jacked off in front of Kelly’s whole group of friends. Since then Becca and her husband Don had been to our house a few times without much happening other than some flirting and...
ThreesomesIt was the summer of 1996. Tom was a sales guy who had been calling on me for the past few months and our companies were now doing business together. Tom was born to sales. He was genuinely a nice guy who wasn’t pushy, very professional, always came through on promises. We had gone out for beers after work a couple of times and were becoming good friends.When Tom called and invited Kelly and me to join him and his girlfriend for dinner on Friday, it seemed like a natural and logical thing to...
ThreesomesIt was Friday, July 4, 1997. Kelly and I had been invited to a surprise fortieth birthday party for a friend of ours. Cliff’s wife Shelly had been planning the party for several weeks and it was quite a shindig. Shelly had a great spread catered in. A co-worker of Cliff’s moonlighted as a bartender and he volunteered to bartend.With a bartender, most of the twenty or so invitees were drinking his delicious (and strong) concoctions instead of slamming cans of beer. The net of it was that...
Group SexIt was August of 1995. Kelly and I were thirty-five. Something that I’ve not shared previously is that Kelly is a big fan of the Mouse House and in particular, their princess animated films. And while she loves the films, Kelly, being Kelly, also enjoyed the idea of putting a sexy twist to things.Kelly has been a seamstress since she was young. She enjoyed making costumes and over the years had made a number of Halloween costumes: Ren-fair and beer wench outfits, even a sexy Dorothy from Oz...
Group SexIt was late July of 1977. Kelly and I were seventeen and had one more year of high school to go. My family were campers and my folks were okay with me inviting Kelly for our weekend at a state campground. Kelly and I drove separate from my folks and my sisters. We were camping with a couple of other families. One was my aunt, uncle, and their sons and the other were long-time family friends with their three kids.Rachel was the oldest of the family friend’s family. She was sixteen, a couple of...
TeenIt was August of 1992. Kelly and I were moving. I had taken a new job that was a few hours and a couple of states away. It was a big raise which made the move worth the effort. Nonetheless, it was hard to leave “home”.Kelly had her own job situation to deal with so as a result, I moved six months before Kelly was able to join me. It actually worked out okay as it gave us plenty of time to house hunt. Well, not entirely true. I was buried with the new job, so most of the hunting fell on Kelly...
Quickie SexIt was early October of 1992. Kelly and I had moved to a new locale just a few weeks earlier. That left us without our usual mechanic. When Kelly’s Mustang started acting up, she decided to take it to a Ford dealer. The problem was specific to higher speed and certain circumstances. Kelly really wanted the service writer to ride with her so she could demonstrate the actual problem and, hopefully, get it fixed on the first visit.It was a Friday afternoon around three o’clock when Kelly arrived....
OccupationsAfter taking an extremely boring Christian ethics class (required by my college, not by choice) on a late Friday afternoon, I checked my cell to see I had a few messages. It was Kelly and she was celebrating a well deserved A on an Calculus test. The first message read: "Got an A in Calc. Vodka n strip gaming my place" Strip gaming is something Kelly got me into and it usually led to sex. However, we quickly learned that there are certain games you just don't play against the other. Kelly...
It was November of 1999. Kelly and I had fallen into an odd tradition. Patrick was our close friend from high school. We’d had four-ways with he and Yvonne countless times over a number of years. Unfortunately, they broke up and Yvonne married a dud. However, Patrick has always been Kelly’s number two.Even after we moved a couple of states away, we would get together a few times each year and Patrick and Kelly would fuck. It had kind of worked out that we would get together the weekend before...
ThreesomesIt was early August of 1985. Kelly and I were both twenty-five. Kelly had an interesting friend in high school. Terri came from a family that was very straight-laced. Terri was the black sheep of her family, probably because Terri liked to fuck. That was exactly what her first boyfriend had told me. Her boyfriend also told me that the more clothes Terri took off, the better looking she became.It was probably the fact that Kelly also loved to fuck that drew her and Terri together. For the most...
Group SexIt was Labor Day weekend of 1993. Kelly was antsy. Kelly had a couple of wild fuck sessions with a wealthy guy (and his vintage car racing) buddies during that summer. But summer was ending too quickly. All summer long Kelly had been running around in tiny bikinis, short skirts, and dresses. She had an incredible tan, had lost a couple of pounds, was keeping everything down south shaved smooth as glass, and her twat was on fire.Earlier that day we had been to the beach where Kelly got to show...
AnalIt was Labor Day weekend of 1993. Kelly was antsy. Kelly had a couple of wild fuck sessions with a wealthy guy (and his vintage car racing) buddies during that summer. But summer was ending too quickly. All summer long Kelly had been running around in tiny bikinis, short skirts, and dresses. She had an incredible tan, had lost a couple of pounds, was keeping everything down south shaved smooth as glass, and her twat was on fire.Earlier that day we had been to the beach where Kelly got to show...
AnalIt was June of 1991. Not too far from where we lived there was a big annual weekend festival with free concerts. Kelly found out that the headlining act for Saturday night was one of her favorite heavy metal ‘hair’ bands from the 1980s.We arrived early afternoon, enjoyed the beach, ate some festival food, and did some people-watching. Around dinner time we entered the large sandy field which served as the concert venue. We staked out a spot about halfway back, between the stage in front and the...
OutdoorIt was the spring of 1980. Kelly and I were a couple of years out of high school. Scott, who you met previously, was a senior. He had been dating Gina for the past few months. She was a sixteen-year-old sophomore.Kelly and Gina both worked part-time at a local bakery. They got along well and Kelly had taken Gina under her wing like a little sister. Gina had started the job around the same time she started dating Scott. Scott, true to his word, never said anything about Kelly giving him his...
Group SexIt was a Saturday night in September of 1980 at the start of Kelly’s junior year of college. I was visiting Kelly and her roommate Tricia at college. Tricia was looking through the entertainment section of the student newspaper and calling out the various deals, activities, etc., that were going on. She got a big case of the giggles when she shared that there was a porn double feature with “Debbie Does Dallas.”The previous spring break was when the dam of sexual tension between Tricia and...
Group Sex