Friends with Benefitsbyjt123©
Jim and Ron had been best friends for many years. They first met in grade school when Ron's family moved to the fairly quiet suburban town to get out of the hectic lifestyle of the big city. They quickly became best friends and remained so all through high school.
Jim and Ron both loved joking around and often kept their friends and classes laughing at their jokes and antics. They quickly gained the reputation of being "class clowns". Both of them were natural hams and always seemed to be joking with each other or doing some sort of silly gag. Neither of them shied away from the spotlight and weren't above making themselves look silly or doing weird things for the sake of a good laugh.
Generally, their joking around didn't get them into too much trouble with their teachers as they were both nice kids and got decent grades. Their joking nature and outgoing personalities made them very popular at school and they had a huge circle of friends.
One of their good friends was Dan. Often during high school Dan would hang out with Jim and Ron. Every year, starting with their sophomore year in high school, Dan threw a huge Halloween party at his place. His parents were really cool about the party and he was the first of their circle of friends to be able to have a party with little parental supervision or involvement.
Each year the party grew a little bigger and a wilder. By the time they were seniors in high school the party was one of the premiere events of the first part of the school year. It was during that party that Dan's parents allowed alcohol, and drinking with a big group of friends in wild costumes only made the party wilder and more fun.
This year Jim was very much looking forward to the party and he was excited that Halloween was now only a few days away. Jim was in his second year at college and he didn't get to see his old friends from his hometown very often. He and Ron had planned on going to the same college but at the last minute Jim received a scholarship offer from another school that was simply too good to pass up. That left him attending college about an hour away from his hometown while Ron attended another school about 45 minutes from his hometown in a different direction.
Jim and Ron still hung out during the summer and over holiday breaks and they managed to visit each other at school a couple of times. Still, Jim missed his best friend and looked forward to Halloween since he knew Ron would also be coming back to their hometown to attend Dan's party.
Dan still lived at home with his parents and attended a small commuter college on the edge of their hometown. He said he had plans to transfer to a bigger school after this school year, but Jim suspected that Dan might be the kind of guy to stay at home with his parents as long as possible.
Dan continued the tradition of his Halloween party even after he and all of his friends started college. It took a lot of planning, but Jim went back home for the party the previous year. He had a great time and was happy to see many of his high school friends there. There was now a new group of people that Dan had met at his college joining the party and so the party was getting still larger by the year.
Dan was one of those guys who went all out for Halloween. His entire house was decorated from top to bottom and he always wore elaborate costumes to his party. He spared no expense and Dan's enthusiasm for the holiday was contagious. Everyone looked forward to its arrival each year and now many of the guests went to elaborate means to create their costumes for the night.
Dan started a new tradition a couple of years earlier to encourage more costumes. He put in some seed money and asked each guest to pay $5 into the pot when they arrived. During the party everyone voted on best costume and the winner got to keep all of the money.
At last year's party the winner of the costume contest received a pretty large cash prize. Jim and Ron were always very competitive and they both put a lot of effort into their costumes for the past couple of years. Jim never quite seemed to have the creative knack of Ron and although his costumes were good they never were good enough.
Ron had nearly won the costume contest each of the last two years. He finished a narrow second the previous year and had been joking all year long that he wouldn't settle for anything less than winning this year. He kept his costume a complete secret but promised it would be unbelievable.
Jim decided to skip his two classes scheduled on Friday and took the bus home from campus on Friday morning. His mom met him at the bus station and they spent the afternoon catching up. He had only been back on campus for a couple of months after spending the summer at home but his mom fussed over him like she hadn't seen him in far longer than that.
After a nice dinner at home with his parents Jim got ready for the party and took the car keys so he could go pick up Ron. Even as Jim drove to Ron's place he had no idea what Ron's costume was going to be. This year Jim had decided to go as a "hipster" from the 1920's. He had a full zoot suit with pinstripes, fancy shoes with spats, pocket watch with chain, and a cool, matching hat. To get himself in the mood he had swing music blaring from his car stereo as he pulled into Ron's driveway.
Ordinarily he and Ron would take dates to the Halloween party, but this year it worked out that they both were between girlfriends. Jim had been dating someone through most of the previous school year, but she dumped him just a few weeks into the current school year. He'd been on a few casual dates since but nothing serious.
Ron had been casually dating a couple of women but neither of them was able or interested in making the drive back to Ron's hometown to spend Halloween with a bunch of Ron's old high school friends. Ron told Jim he didn't really think these relationships were going very far anyway so he wasn't all that worried about it.
The end result was that neither Jim nor Ron had a date this year and so they ended up going together. Jim didn't mind too much as he was looking forward to hanging out with Ron. Besides, he thought that the party might be a good place to try and pick someone up. There were several good looking women from his high school he wouldn't mind hooking up with and last year there had also been a few hot women from Dan's college in attendance.
When Ron opened his front door Jim froze for a second and his jaw dropped open. Jim then exploded into wild laughter. He laughed so hard that he had to lean against the door frame to hold himself up. "What the hell is that?" Jim finally gasped between bursts of laughter.
"What?" Ron asked, "Haven't you ever met my twin sister before?"
Ron had dressed completely in drag for the night. However, this wasn't just a guy throwing on a dress. As usual, Ron had gotten 100% into his costume and had completely dressed in drag for the night. He wore a wig with long, straight black hair, and under his top he wore big, fake tits. He wore a black skirt that was fairly tight and came down to about his knees. Underneath he wore a pair of black fishnet nylons and a pair of black shoes with a short heel.
"Did you fucking shave your legs?" Jim asked.
"Of course," Ron replied, "I told you I was going to win the contest this year."
Jim then looked at Ron's face and asked, "Is that make up?"
"Yup," Ron answered. "My sister never goes anywhere without her makeup."
"Well then," Jim said as they stepped out on the front porch and walked toward the car, "may I just be the first to tell you that you are perhaps the ugliest woman I have ever seen."
They joked and laughed about Ron's costume all the way to Dan's house. At one point Ron said, "Hey man, check this out." He then lifted up his skirt and showed Jim what he called the final touch.
"You've got to be kidding me," Jim said when he saw the top of the nylons on Ron's thighs. "Are you wearing a garter belt?"
Ron laughed and said he thought it was the perfect final touch. "If you don't win the contest I'll be anxious to see who does," Jim said.
Dan went wild for Ron's costume when he answered the door. The three of them joked and laughed as Dan asked Ron where he found the clothes. Dan got his date and she almost choked on her drink when she saw Ron. Before Dan led Jim and Ron downstairs to where the rest of the party was happening he told them to wait.
Dan went to the bottom of the stairs and yelled over the music that he had some bad news. "I've just learned that our good friend Ron won't be able to join us tonight," Dan said. "All is not lost however as he was able to find a member of his family to take his place here tonight with us." He then flourished his hands and said, "I'm pleased to present Rhonda, Ron's twin sister."
With that Jim and Ron came downstairs. The room erupted with wild laughter as "Rhonda" smiled and waved and made her way around the room introducing herself to everyone. Ron's costume was obviously a big hit.
The party, as usual, was great. The drinks flowed freely and everyone was having a great time. Some of their friends teased Jim about his "date" for the night. "Does Ron know you've got a thing for his sister?" a few of them asked.
Sensing an opportunity to get a good laugh Jim and Ron played up the idea that they were dates for the night. "Rhonda" started telling people what a great guy Jim was and how he was really good in bed. Jim countered by telling how "Rhonda" had this really kinky side. They kept up this sort of joking banter all night.
At one point a couple of people teased Jim and told him to kiss his date. As the crowd burst into a wild cheer Ron "kissed" Jim on the lips but put his hand in between their mouths. Still, they kept up the act like they were really getting into their kiss and the crowd whistled and cheered them on.
As the party continued things got wilder. Even more than in past years the party started getting a little kinky and sexual. Some couples were openly fondling each other as they danced and others were off in dark corners wildly kissing.
The atmosphere was exciting and a little erotic and Jim was eager to find someone to hook up with. With all the good looking women and the sight of the other couples fondling or kissing Jim was getting very horny. Soon Jim focused his attention on Cindy, a girl he had gone to high school with. He and Cindy had an on-again off-again sort of relationship in high school. Jim was always interested in Cindy but most of the time it seemed Cindy was just interested in teasing Jim or in stringing him along. Tonight Cindy seemed pretty receptive to his flirtations and she was definitely flirting back. Cindy was always a bit of a tease but Jim hoped that tonight might actually lead to something.
Ron had been flirting and dancing with Michelle, a friend of Cindy's from college that Cindy had brought with her. Michelle seemed really nice and was really good looking. It seemed that she and Ron were really hitting it off.
During one song Ron and Michelle ended up dancing right beside Cindy and Jim. Near the end of the song Dan and a few of their friends started teasing Jim and "Rhonda" and asking whey they weren't dancing with each other. Dan called out that he was going to tell Ron that Jim wasn't doing a very good job of showing "Rhonda" a good time.
Right on cue Jim and Ron stepped away from their partners and started to dance. Dan put on a slow song and the crowd cheered wildly as they put their arms around each other. They left a good foot of space between them as they danced but the crowd still went wild. Jim and Ron continued to play it up as they danced through the rest of the song.
When the song finished they returned to Cindy and Michelle. Cindy now had a mischievous look in her eye that Jim recognized easily. Based on his past experiences with her this look either meant he was going to be in store for a wild time later or that he would end the night very frustrated after she teased him unmercifully all night long.
Jim's hopes were raised when he and Cindy danced again because she seemed very excited. She immediately groped his ass and soon they fondled each other's asses as she rubbed her pussy against his crotch. They kissed a couple of times but she always parted the kiss after just a brief time.
The party got wilder and more lust filled as the night went on. At one point when the four of them were talking Cindy commented to Michelle, but in a way that made it obvious she was also talking to Jim and Ron, that she thought it was really hot watching Jim and "Rhonda" dance together earlier. She then added that she'd love to see them dance again.
Not missing a beat, Ron replied that he'd be happy to do it if Cindy and Michelle agreed to also dance together. Cindy gave a wicked smile and she and Michelle looked at each other for a moment before Cindy replied, "OK, you're on."
Like most of his friends, Jim would do just about anything to watch two women together sexually. He had a collection of lesbian porn, and fantasies of women fucking or even just kissing each other were common for him. Both Cindy and Michelle were really good looking and the thought of watching them dance together was enough to make his cock twitch.
This was especially true tonight as both were dressed in sexy costumes. Cindy was dressed as a naughty witch. Her costume really wasn't that elaborate as it basically consisted of a pointy witch hat. Otherwise she wore a skimpy black dress that Jim had seen her wear once before. The dress was short and stopped well before the halfway point of her thighs leaving the majority of her legs on display. Tonight she wore black nylons and black high heeled shoes. The collar of the dress dipped fairly low in front but in back the dress was open all the way down to her ass leaving her entire back exposed. She looked sexy as hell.
Michelle was dressed as a baseball player, and she was definitely the hottest baseball player Jim had ever seen. Her pinstriped pants hugged her like a second skin and beautifully displayed her ass. The top three buttons on the uniform top were open and Michelle's huge tits and deep cleavage were easily visible. The uniform top was nearly as tight as her pants and only added to the allure of her big tits.
"You first," Cindy said motioning out to the dance floor.
Jim and Ron stepped in front of the two women and started to dance again like they had done before. Cindy leaned toward them and said, "If you want to see us dance you're going to have to do better than that." She pushed them toward each other and said, "Come on boys, let's have some fun."
Suddenly Jim and Ron found themselves pressed against each other as they danced. For a few moments Jim wondered if Cindy wasn't just trying to make them look foolish, but then Cindy held out her hand to Michelle and the two women copied Jim and Ron's embrace and danced right beside them. Seeing Michelle's hands come to rest on Cindy's bare back and seeing Michelle's big tits press tightly against Cindy's chest made Jim's stomach knot.
They stayed like this until the song ended and then Jim went back to Cindy and Ron to Michelle. They danced for a bit longer before Cindy asked Jim if he liked seeing her dance with Michelle. Jim answered yes and she asked if he'd like to see them do more. Jim nodded and Cindy moved over to Ron and whispered something into his ear. He looked at her excitedly and then, with less hesitation this time, Jim and Ron started dancing together again.
Cindy and Michelle watched for a while before Cindy said, "So why don't you show me what you'd like to see us do?"
As Jim still stared at Cindy he felt Ron's hands immediately slide down his back until Ron was groping his ass. Jim shot Ron a quick look but Ron muttered, "Relax dude, I'm dying to see those two together."
When Jim turned back toward Cindy and Michelle they were now dancing together. After only a few seconds Cindy's hand slipped down Michelle's back until Cindy was caressing her friend's ass. Soon Michelle started groping Cindy's ass. The sight of the two women fondling each other drove Jim wild. He then got an idea and reached up to massage and caress one of Ron's big, fake tits.
Cindy smiled wickedly and her hand slowly crept up toward Michelle's tits. It seemed to take forever and the anticipation was driving Jim crazy. When Cindy's hand finally reached Michelle's tit Ron moaned excitedly and Jim stared with wild lust.
Cindy continued fondling Michelle's tit as Jim did the same to Ron's fake tit. Michelle continued to massage and caress Cindy's ass as Ron had kept his hands on Jim's ass. Jim was so caught up in watching the two women that he wasn't really aware of what was happening until he noticed that something felt different. Jim pulled enough of his attention away from the women to realize that his cock had grown hard from his excitement. That, however, was only part of what he now felt. It took him a few seconds to realize that he was also now feeling Ron's hard cock rubbing against him as they danced. Occasionally their cocks rubbed against one another through the fabric of their clothes. Being like this with his friend made him feel a little strange but he was so excited and distracted by watching Michelle and Cindy he didn't think much about it.
After a while longer Cindy and Michelle parted their erotic embrace. Cindy and Jim moved back together and resumed dancing. At this point, however, their dancing was little more than wild groping and deep kissing. A quick glance over at Ron and Michelle showed that they were doing the same thing.
Jim caressed Cindy's soft ass and let his tongue eagerly slide against hers as they traded a long, excited kiss. His cock was still rock hard and he excitedly pressed it against her wanting her to feel how hard he was. Jim had fucked Cindy once before and he was sure that tonight was going to be a second chance. He had never seen her so wild and willing and there was every indication from her kisses and her excited caresses that she wasn't just teasing tonight.
Cindy kissed her way across Jim's cheek toward his ear and then whispered, "Do you want to see me kiss Michelle?"
"Yes," Jim groaned.
"Good," Cindy giggled. She then pulled Michelle into one of the darker corners of the room as Jim and Ron eagerly followed. By now the party had descended into a series of pairings all wildly making out or otherwise so involved with each other that nobody was really paying much attention to anyone else.
This was especially true in the dark corner where they finally stopped. Cindy pulled Michelle close and for a moment Jim thought they would kiss. Instead, Cindy stopped just short of kissing her and looked expectantly at Jim and Ron. "You first," she said.
Jim and Ron looked at each other not sure of what to do. Ron shrugged and said, "Are we ever going to have a better chance to see them kiss? I guess I'm game if you are."
Jim didn't know what to do, but seeing Cindy and Michelle on the verge of kissing didn't leave him thinking straight. He needed to see them kiss and before he realized he was doing it he gave Ron a quick nod even as his gaze returned to Cindy and Michelle. Ron moved to Jim and soon their lips came together and they gave each other a cautious, tentative kiss on the lips.
The kiss ended pretty quickly and they turned to look at Cindy and Michelle. "I don't know," Cindy teased. "I guess that was pretty good, but I was thinking more of something like this." With that she turned to Michelle and the two women met in a long, deep kiss that seemed to last for several minutes. Jim could see their lips part and their tongues dance as the kiss continued. He had never before seen anything as hot or wild as this kiss.