Some Girls are Different

"Mister Jones, will a king size bed be ok?" said the woman at the hotel's front desk.

"Yes, that's fine" Jim said as he put his credit card back into his wallet. "Thank you..." as he looked at her name tag, "..Amy. Do you have any recommendations for fun places to visit around here?"

"Hmmm...that depends on what type of fun you are looking for. There are the normal places - dive bars, there's the river walk downtown." she trailed off. "All set. Here is your key card. You are room 417. The elevator is to the left." She gave Jim a devious look. "If you are looking for something...different, I recommend the club on 17th Street and Broadway."

Jim raised an eyebrow. He was intrigued. He liked to try different things when he was on travel for work. He wouldn't have to show up at the customer's site until mid-morning. That meant, he could be out late and have some fun. "What kind of different?"

"You're an attractive guy. How open-minded are you? How"..she paused..."wild...do you like to get?" Again, that devious grin showed up on her face.

Jim blushed. Now Jim was really curious. "I'm pretty open-minded."

"Good. I would plan on getting there between 10 and 10:30. The main attractions usually show up around 11, but the place fills up quickly. I'll be going there tonight as well - my shift here ends at 8pm." she said, that grin still prominent on her face.

Jim thought Amy was quite attractive. She was at least 5' 7" with a lean figure, long auburn hair, and deep blue eyes. She was exactly his type. Since she said she was going, it didn't matter if the club was going to be interesting or not. - he'd go just based on the fact that she said she was going. The fact that she said he was attractive was icing on the cake. "I'll see you there!" he said with a big smile.

Amy smiled at him, gave him a wink and said, "See you later, cutie."

With that, Jim grabbed his luggage and headed to his room. He had some time to eat and get cleaned up for the night's festivities. Once he got to his room, he put his bag on the bed and his suitcase on the floor. He grabbed a few things out of it and headed for the door. He was hoping to run into Amy at the front desk again, but she must have been in the office in the back. A young man was at the front desk. He smiled as Jim walked by and out the door.

Jim headed across the street to the brew pub that he saw on the way in. Dinner was uneventful. He ate at the bar and got eyes from a cute woman who was walking by on her way to the ladies room. He paid his bill and headed back to the hotel. Amy still wasn't at the front desk, so he walked right by and headed up the elevator to his room. He was wondering what type of club it was. He was no stranger to alternative clubs or even alternative relationships. He had once dated a man, but that didn't last long. He had decided after a few dates that they were not compatible. Jim dated a few women, but his favorite past relationship was with a pre-operative transsexual woman. He had made all of the stupid mistakes with her, misgendering her when he was angry with her, asking her what her "real" name was when they first met, using the term "shemale" and assuming that she liked using her penis. She put up with him for a few months, but decided that she couldn't handle teaching him how not to be a jerk. That was a few months ago now. To his credit, Jim actually learned some valuable lessons from her and vowed not to treat any woman like that again, regardless of her physical gender.

He thought to himself, "Hopefully I get to spend some time with Amy." He thought to himself, maybe this was a kinky club and she was into things like pegging. He decided to take a shower and clean himself out thoroughly. He shaved what little body hair he had while he was in there. After his shower, he put on a hot pink thong, a pair of jeans, and a nice shirt. He hoped the dress code for the club wasn't too strict. He also hoped that Amy was as open-minded as he was.

He headed downstairs and out the door to his rental car. He put the intersection into his GPS and headed off. Once at the club, he parked and noticed there were not too many people lined up outside. To his relief, most of the guys were wearing jeans. He wondered if any of them were sporting a hot pink surprise in their pants though. He chuckled to himself. As he approached the door, the bouncer looked him over, and told him there was a $10 cover charge. He paid the cover and was waved in. It was just after 10 PM, but the club was already hopping. He scanned the crowd and noted that there were some very attractive people there. He spotted a group of women that he thought were gorgeous. There were several women in the club who wore what looked like dominatrix outfits with chains attached to men wearing rubber masks with collars. Bingo. This was his type of place. Suddenly, he felt somewhat out of place being dressed so tamely. At least he had his thong on.

He walked up to the bar and ordered a beer. The bartender was a very large, hairy guy, but clearly a teddy bear. He winked at Jim and asked, "New here, eh? What kind of things do you like?" Somewhat nervous, Jim responded with "Hmmm...I tend to like the girls" using air quotes as he said the word "girls" "Jim's the name"

"Bill. Ever been with one of the girls before?" as he shook Jim's hand.

"Yeah, I dated one. Really screwed things up. I pretty much made every mistake in the book and she still put up with me. For a while at least."

"Bummer." Pointing to the group of girls that Jim saw on the way in, "Those girls are regulars...nice girls, a few of them tend to take charge, if you know what I mean. They come here quite a bit and they are probably what you are looking for. This group over here on the left, they are working, so if that's not your thing, you might want to steer clear. If you want a real dom, head over to the tables to the far right. Jasmine usually hangs out there. I'm sure she has an extra leash with her."

"Thanks for the tips!" Jim said smiling. He grabbed his beer and headed to the large group of women. He hadn't realized it, but Amy was in that group. As he was about to introduce himself, Amy noticed him and said "Hi Jim! This is Jim! Sit over here with me!"

"How can I refuse that?" Jim said as he headed towards the empty seat next to Amy. He mustered up all the smoothness he could, "Hello ladies." Amy proceeded to introduce him to the rest of her friends, "Gisella, Lisa, Katrina, Jessica, Alexis, Allison, and Katie."

"Nice to meet you all." Jim said as he was attempting to memorize their names. He wasn't all that good with names, so he admitted, "Please forgive me, but I'll probably mess up your names - I'm terrible with them."

"No worries" Alexis said as several of the other girls nodded in agreement.

Jim noticed that several of the girls were eyeing him up and down. Amy was nonchalantly moving closer to him and two of the other girls gave Amy a slight mocking scowl. "Already claimed your fun for the night, eh, Amy?" Lisa said giving her a wink. Amy, getting bolder, put her hand on Jim's leg and said, "You know it."

Jim felt a stirring in his thong when she did that. He liked aggressive women. He like aggressive transwomen even more although he still wasn't sure if Amy or any of the other girls here were trans. Either way, he was thrilled that such a good looking woman was flirting with him. The girls idly chatted about the last guy that Lisa and Jessica met a week ago. "He seemed pretty macho, so I wasn't sure if he'd let us double-team him." said Jessica. "Turns out, if you get him turned on enough, he was willing to do EVERYTHING." she said with a sly smile. Lisa nodded.

Amy turned to Jim and said, "In case you haven't figured it out, we are not like most girls. Several of us tend to like to take charge. Lisa, Jessica, and I are total tops. Most of the rest of us are versatile, except for Katie who is strictly a bottom."

Jim's eyes almost popped out of his head. "Tops? As in not the receiver?"

"Oh yeah" Lisa said. "I absolutely love getting blowjobs and Jessica is a huge ass-girl. This guy was willing to let both of us do him at the same time. Most macho guys I've been with are ok with one-on-one, but turn into chickens when a second girl is in the room."

At this point, Jim was blushing and the girls each had huge grins on their faces - Amy included. "I hope you are open-minded enough to have some fun with us tonight, Jim" said Amy.

Jim took a big swig from his beer for effect, and managed to eek out "Uh...yeah." The girls all chuckled.

"Let's dance." Lisa said to the rest of them. Amy and Jessica both grabbed Jim's hands and dragged him to the dance floor. It was obvious to him that he didn't have a choice in the matter.

By this time, the club was getting full and the music was thumping. The girls all clumped together on the floor, gently easing a few other people out of the way. Jim was on the outskirts of the group, but had Amy in front of him and Jessica behind him. Amy was facing him and started to get closer to him. Jim wasn't all that good at dancing, but the girls were good sports about it. Jessica was starting to grind into his backside. He was half expecting to feel something rubbing into his ass, but she was still smooth there. She leaned forward and whispered into his ear, "I can't wait to do this with you later with less clothes on." She nibbled on his ear sending a shockwave through him. Amy was in front of him starting to grind herself into his front side. She put her hands on his hips and pulled him closer. He was surprised that he didn't feel any bulge in her skirt either. She must have sensed that and said to him "We all do a very good job at tucking. Don't worry, if you play your cards right, you will get to see it later." She gave him the sly smile again.

By this time, Jim couldn't take it any more. He started to get an erection. Both girls grinding on him sensed it and took it as an invitation to be even more bold. Amy said to Jessica, making sure Jim could hear it, "We should double-team him tonight. My place?"

"Mmmmm...I wonder if he will be able to handle us." Jessica said as she looked into his eyes.

"Let's get another drink and then head out." said Amy. Jim and Jessica agreed and headed back to the table. Meanwhile, the other girls were starting to attract attention from several other guys near the dance floor and they started to pair off. At the table, Jim asked the ladies what they were drinking.

Amy answered, "Cosmo"

Jessica answered, "Mojito."

Jim said, "Be right back." and headed to the bar.

At the bar, Bill gave Jim a knowing smile and said, "Let me guess. Cosmo, Mojito, and a beer for you." He didn't even wait for an answer before he started making the drinks. Jim paid and gave Bill a good tip as Bill gave him a wink.

Jim headed back to the table with the drinks. Both Amy and Jessica smiled at him as he sat down. "I feel so lucky to hang out with you two beauties."

"Awwww...flattery will get you everywhere." said Jessica. "But mostly pinned under me." she said with a devilish grin.

The three of them drank their drinks as they chatted. Jim asked, "So how do you all know each other?"

Amy responded with, "Well, most of us actually met either in high school or just after. A bunch of us were on the boys soccer team in high school together. We were uber competitive. One Halloween, several of us independently dressed as girls. It wasn't one of those half-assed attempts. We each went all out and were shocked to see who did it. What a blast that was."

"Cool. So you've been friends for a long time now, then?"

"Yes. I think each one of us has hooked up with each other also." laughed Amy. They chatted more while both girls moved closer to Jim. All three were touching and starting to get really excited. "Let's get out of here." said Amy to the other two.

"Agreed." Jessica and Jim both said in almost unison.

The three all got up and headed to the door. They caught the eyes of the other girls who gave knowing smiles and waved. "Jim, you can leave your car here. We can walk to my apartment. It's only two blocks away." said Amy.

By this time, Jim was ready to burst. He was nervous since he had never been with two women at once, and he definitely had not been with two hot transwomen. They arrived at Amy's apartment and she opened the door. They all went in and Amy pointed towards the couch and told them to get comfortable. She fixed a few drinks and sat down on the couch next to Jim. Jessica had already started to make out with him. Amy gently grabbed his face and turned it to her and kissed him deeply. This alone was almost too much for him to take. His erection was starting to show through his jeans. He was starting to get nervous that the girls would think he was a weirdo for wearing a hot pink thong. Amy, sensing his slight discomfort, pulled her shirt off, revealing a satiny pink bra. Jessica followed suit and was wearing a purple lacy bra. Jim guessed that Amy had a B cup and Jessica had a C cup. He pulled his shirt off. The girls both kicked off their heels and started to pull their skirts off, revealing thongs that matched their bras. Jessica had on a garter with stockings. Amy was bare legged. Neither girl showed a bulge in her thong though.

Jim took a deep breath and started to kick his shoes off and pull his pants down. Both girls gasped and then squealed at the sight of his hot pink thong. "Somebody is a naughty boy" said Jessica as she bit her bottom lip. Amy grabbed both of their hands and dragged them to her bedroom. She had a king size bed. Amy pushed Jim onto the bed on his back while she and Jessica stood at the end of the bed. She looked at Jessica and said, "Ready?" with a wink. Together, they both took their bras off, revealing very perky breasts. Jim was in heaven. They then both slid their thongs to the side, letting their rather large penises out. Jim guessed that they were both larger than his, but not by much. Still, he was intimidated as he had only had a strap-on used on him a few times. His former trans girlfriend was a strict bottom, so she had never penetrated him. These two had a much different plan in mind. They both climbed on to the bed on either side of his head, leaving each penis a few inches from his mouth on either side. Jim took this as a hint to start sucking. He turned to his left and took Amy into his mouth. She groaned as he tried to work it as deeply into his mouth as he could. Meanwhile, Jessica started to stroke herself. He could see that she was getting much larger at this point.

He let Amy's penis plop out of his mouth and turned to the right and took Jessica's penis into his mouth. Amy started to stroke hers. Jim couldn't get even half of her penis into his mouth. Amy decided to tease him a bit. She straddled him and rubbed her butt along his penis. Jessica wasn't about to let him slow down with her blowjob. She straddled his head titling her body so she could get better leverage into his throat. She pushed it deeper into his throat and he gagged a little. She pulled it out a bit and pushed it back in. Amy was still rubbing her butt along his penis and she could feel his precum leaking out. She grabbed a dollop of his precum and reached around to push her fingers into his mouth just as Jessica pulled out all the way. "I think somebody is excited" Amy said.

"Ooooh yeah" moaned Jessica as she pushed her penis back into his mouth. Amy grabbed a condom off one of the night stands and waved it in Jim's face. She made it seem like she was handing it to him, then smiled with a devilish smile and ripped it open herself. She got up off of him and made of show of putting it on her penis. She positioned herself at Jim's legs. She grabbed his legs and slid forward as she lifted them up to her shoulders. She positioned her penis at his backside and rubbed it there for a few minutes. She reached to her nightstand again to grab some lube. She dribbled it liberally into his asshole and onto her rock-hard penis. Jim tensed up when he felt the cool liquid hit his skin. She wiggled her penis around the area more to warm it up. He loosened up and she started to push in.

Meanwhile, Jessica was face-fucking him. Jim was proud as she was almost able to go all the way in without him gagging at this point. Jim could taste Jessica's precum when she pulled out. It had a sweet flavor and he was excited to get a taste of her cum. She was moaning very loudly at this point.

Amy was determined to give Jim a good fucking. She started to push harder and finally got her head to pop past his ring. He let out a groan when she popped in. Once in, she pushed a bit further and then slowly pulled out. She dribbled a bit more lube onto her shaft and pushed it back in. This time, with a bit more speed. She continued this for a few minutes to get him used to having something as large as her penis in his butt. Jim was loving this. Nowhere in his wildest dreams did he ever think he'd have one hot transwoman fucking him, never mind having a second one pushing her rather large cock into his throat.

Jessica started to pick up her pace and Jim knew what was about to happen. She pushed very deeply into him, getting her balls to smack his chin and her small patch of pubes to rub up against his lips. She paused all the way in and pulled out half way. She immediately pushed in all the way again and paused. "I'm about to cum!" She pulled out and pushed in one last time. He could feel her spasm as she groaned. He couldn't believe that she shot the first of her load directly into his throat. She pulled out so the tip was still in his mouth. She was still cumming. He could taste her sweet and salty load. She filled up his mouth and a little came dribbling out the side. She looked down at him and smiled, and then climbed off of him. She lay down on the bed next to him, spent.

Meanwhile, Amy was pumping at his ass. At this point, she was able to push all the way in, her balls slapping the bottom of his ass when she buried herself to the hilt. Jim was getting the rhythm now and was tensing his ass as she was pulling out, milking her. This was almost too much for Amy to take. Jim was close to climaxing as well. He had never experienced an anal orgasm, but it was starting to feel very intense. She was able to pump two more times before she let out a groan. Jim could feel her tense up and spasm as she filled the condom deep in his ass. Jim shot his load at the same time, but instead of shooting into the air, several huge gobs of cum leaked out of his penis and dribbled down the shaft. She collapsed on him and kissed him, still buried deeply in his ass. She could taste some of Jessica's cum, still in his mouth. She licked his face where some of Jessica's cum had leaked out. Jessica chuckled at this. Amy slowly pulled out of Jim's ass, holding the condom on her softening penis. She pulled the condom off, careful not to leak any out of the tip. She held the condom up to him and got another one of her devilish grins on her face. She pulled his chin down, opening his mouth and positioned the condom above his head. She slowly turned it over, draining it into his waiting mouth. Her cum was a bit more bitter, but he still enjoyed the taste.

Jim started making a gargling sound and then swallowed the entire load. Both girls laughed. Jim said, "I could REALLY get used to this!" The girls nodded in agreement as Amy slid onto her back on the other side of Jim. The three of them basked in post-orgasmic bliss for several minutes before anybody spoke again.

Amy said, "Jim, I'm so glad you decided to come out tonight. I had a feeling about you."

Jim nodded in agreement.

Jessica was about ready for round two. Since Amy had loosened him up, she was sure she'd be able to pound him without hurting him too much. She rolled Jim onto his hands and knees. She pushed down on his shoulders and positioned herself behind him. She grabbed a condom from the nightstand and rolled it onto her penis. She dribbled some lube onto her shaft and into his, now quite loosened, hole. Despite being used to Amy's slightly large penis at this point, he was still a bit apprehensive at Jessica's much larger one. She pushed in with a single continuous, slow motion. She buried herself to the hilt in his ass as he grunted. She started to saw in and out as he pushed his head into the pillows.