Tricia arose from sleeping in on her day off, she worked a regular office job, and had wrangled a day off. She was in her 20s, and she had let her blonde hair grow out some, although it didn't matter as much since for her job she usually kept her hair in a pony tail, or up in a bun. She normally awoke in the morning next to her boyfriend, Holden, but he was unable to get a day off of work, he worked for the city. She sat up in bed, and began to think about her secret plan for her husband that she had already put into action. She had put a note in his lunchbox giving him a phone number to call, it was the number to a hotel that she had already reserved a room in. Unfortunately before she could enact the rest of her plan it required her to have to wait until after Holden was off of work. However she began thinking more and more about what would happen, and she found herself getting more and more turned on, she bit her lip, debating internally as to whether or not she wanted to store up all her energy for the night, but Tricia, being impatient, reached for her bedside drawer, which contained a vibrator, which she turn on and slid below the covers, and down to her wet pussy, and inserted it, letting out a soft moan as she did....
After finishing and showering she went about getting some of the things ready for the night, including calling her friend Kelly, who was her partner in crime for the night. Kelly answered her phone after a few seconds of the song "Don't Cha" being played. "Hey there sexy," she said to her long time friend. They had met as freshman roommates in college, and became best friends through the years, and had shared many things throughout their years of friendship.
"I'm good, ready to run some errands for tonight?" Tricia asked.
"Of course, so you're 100% sure that Holden will enjoy this?"
"Absolutely, if you would have seen what I saw on his computer, you would know it for sure." Tricia responded, ultra confident
"It may be a good idea for me to see it, just to get a better idea of what he is looking for"
"Good idea, want to come over here and I'll show you before running the outfits are on reserve for the day, so all we have to do is get there before 7." It was noon when Tricia said that, and it was not until 1 that Kelly showed up at her door. Kelly was tall for a woman, around 5'10", a few inches taller than Tricia, and the same age, except her hair was red, and more styled than Tricia's, going down past her shoulders, the ends hanging down to the top of her C cup breasts, which were a very well proportioned part of her very fem looking body.
"So where is the computer?" Kelly asked, after a hug between the two.
"Right through here," Tricia said, "I've also got some of the stuff picked up; it's out on the bed now." They walked into the bedroom first; a few toys were put out onto the bed, including two strap-ons, and a few sets of handcuffs. "These go with the outfits for the night." Tricia said.
"What about the prostitute costume?" Kelly asked anxiously. Tricia held up the incredibly short skirt, skimpy halter top, as well as some stockings and some very high platform heels that would add about 6" to the height of anyone wearing them. "Very hot," Kelly said, the wheels turning in her head about the possibilities. Kelly noticed something else out on the bed, half covered by the comforter and half not, and it was Tricia's aforementioned vibrator that she neglected to put away. "Have a little fun this morning?" Kelly asked, looking at the vibrator.
Tricia just looked back at her with a devilish little grin "I got really excited thinking about tonight."
"Unable to control yourself?"
"Never have been before, why start now?"
"I think I'm having that some feeling right now though, do you mind?" Kelly said to her, as she begin wiggling out of her jeans, letting them fall to the ground to reveal a black thong, Tricia moved over to the bed too, and as Kelly laid down she laid down next to her, kissing her full on the lips, their tongues intertwining. Both were flooded by memories of their college lives, when they were both single they had been lovers in much this same way. Both owned vibrators, and they loved to play with their toys, and they enjoyed being single more than having boyfriends at times. Tricia's hands began to go to work, one reaching down and rubbing Kelly's pussy, not penetrating it, but merely teasing, as she grabbed the vibrator and began doing the same thing.
"Do you want the vibe now slut?" Tricia said between kisses. She turned the vibrator onto low as she finished the sentence.
"Yes, please Trish, this slut needs it right now." Tricia needed no further prompting and she plunged the vibrator deep inside of Kelly, turning the speed onto medium. She also moved her own body, and shifted her own panties out of the way, lifting her skirt with one hand and putting her pussy right onto Kelly's mouth.
"How much pleasure you receive from this vibrator is going to be very dependent on how well you do on my end," Tricia said and Kelly knew exactly what she was doing, she had grown very good at this throughout their college career, and almost immediately Tricia began to moan, which increased the speed of the vibe, and Kelly let out a moan, but Tricia couldn't hear it, just feel it, she pushed the vibe farther in, and started moving it in and out of Kelly's sopping wet pussy quickly, making a smacking sound from her natural lubrication. Kelly's tongue was hard at work on Trisha's pussy, moving around and licking every inch it could reach. Trisha began moving her body back and forth as she got more and more turned on, her pussy sliding up and down Kelly's face, her juices covering it.
Holden worked for the city, it was mainly clerical work, nothing exciting, but it was a living, and the city always had lots of bureaucracy so his job would be secure. He was only about 5'9" and kept in good shape, he wasn't muscular but he wasn't fat either. He was a decent athlete in college, and swam as a walk-on back in college. It led him to a habit that Tricia thought was strange initially, he kept himself totally shaved. She got used to it, and even helped out on occasion. The only hair he had was on his head, hi brown hair kept fairly short, and he was trying to train it to stick up from his head, and hoping that it stayed with him as he aged. He was a few years older than his girlfriend, and they had met 2 years ago, dating for about a year before deciding to move in together. As he went to go and eat his lunch in a local park, it was around 2:30 when he did, a very late lunch due to meetings, which he often did to get some fresh air during the day he found a note on the bottom. It said "Marriot downtown, room 814, be there at 6, I love you" and it was signed by Tricia. This kind of thing had happened before, and Holden immediately tried to think of some kind of special relationship event that may have slipped his mind. He checked his PDA, where he marked all of those things down, and became a little perplexed as to why she had picked tonight when their anniversary was just 2 weeks away. He attempted to call her, but the phone kept ringing, with no answer. He finished his lunch and went back to work, but was obviously unable to devote his full attention to it, and he watched the hanging wall clock tick tock away the seconds, and minutes until he was going to be able to leave.
As 5:45 rolled around Holden left his office, and went to his car, he was already downtown, so all he had to do was walk over to the hotel, and go to the room. He walked in, went to the elevators and found the room with no trouble at all. He knocked on the door, and Tricia opened it, greeting him with a full on kiss, and inviting him in. The room was a suite, with a door on either side for a bedroom. Tricia sat him down on the couch, and said "Honey, I need to talk to you about something." Holden just kind of nodded, tacitly giving her the go-ahead. "Well I was doing a few things on the computer, and I found a few things that I was a little surprised to see, and seeing how we're the only two people who use it, I knew it must be things that you were looking at."
Holden's heart sank a little; he knew exactly what she was talking about. Holden had a fetish for cross dressing, he enjoyed reading stories about men being transformed by wives or girlfriends into women, there were also pictures on the system. He had kept it secret from Trish. Holden started to speak, but Tricia cut him off "I want you to know that if this is something that you enjoy, then I want to help and be involved, the only thing that I don't like about it is that you didn't tell me, you know I am open about things, and I had a lot of wild times back in college."
"I know, it was just hard for me to think of how to tell you, and I was worried you would think it was because I'm not happy, which I am. I guess I was just afraid of your reaction."
"So my reaction so far would be your best-case scenario?" Tricia said, smiling at him.
"Yeah, I'm a little surprised." Holden said, the butterflies flying out of his stomach, never to return.
"Well, follow me," Tricia said, standing up and grabbing his hand, leading him into one of the bedrooms. It had the prostitute outfit laid out on the bed, and in the bathroom there was a full set of make up that Tricia had picked up, as well as a blonde wig that was about shoulder length. Holden was shocked that she had gone to this much effort, and excitedly asked "Where do we start?"
"First, get dressed in that outfit on the bed," Tricia said. Holden looked at the outfit, and quickly stripped out of his work clothes, putting on the leather panties with a strategically placed slit in the back. "Tuck yourself back so you don't have a bulge baby." Tricia reminded him. He sat on the bed and put the rest of the outfit on, including a bra that contained some small falsies that helped his figure out some. Lastly she put on the heels and wobbled a little on them before re-gaining balance. Tricia stood up, looking at her boyfriend and led him to the bathroom, sitting him on a chair in front of the mirror. She began putting make up on him, first dark red lipstick, some base, rosy blush, and some blue eye shadow. She gave him tips on how to do it while she did, telling him "I wanted him to be able to do it by yourself so you could surprise me every once in awhile." After Tricia looked at her work she put the wig on him, and the transformation was complete. He looked like a totally different person, and his face had a look of awe on it.
"I never thought this would ever happen, and you did such a great job." Holden said.
"Yeah, you look like a hot little slut, Holly." Tricia kissed him on the cheek. "Now I will be back in about 20 minutes" she then produced a little note "I want you to read this so you'll have a bit better idea of what is going on. I love you, and be a good girl." Tricia walked out of the room, and back into the other bedroom where Kelly was waiting anxiously.
"Well...?" Kelly asked.
"It went perfectly, you would not believe how different he looks, she looks." Tricia said, giggling a little bit at the end. "I see you are all dressed." Kelly was, she was had on a blue shirt that had a few buttons undone to show off cleavage, as well as some slacks, her hair was hid somewhat by a police hat, and she had on large aviator-style sunglasses. She also had knee high boots on with 5" heels that made her a very imposing figure. "Did you remember to put your little surprise on?" Tricia asked.
"Oh yes, I love the feeling of having it on, but then again that was something you introduced me to." The surprise was a 6" strap on dildo that was hiding in her slacks; with the use of a sheath she was able to keep it from bulging noticeably. Tricia hurriedly got ready, nearly forgetting to put the sheath on hers before putting on an identical outfit and boots, her hair also hanging down, with the same sunglasses, and similar style make up. Besides the height and hair color differences they looked almost exactly alike.
"We are definitely two hot cops" Kelly said, admiring both of them in the mirror. "Don't forget the handcuffs" Kelly grabbed two pairs, as did Tricia. She then turned to her friend and asked "Do you think he's ready? Or should we make him wait some?"
"You know patience isn't a virtue that I was blessed with," Tricia responded, and they walked out the door.
Holly was reading through the note again, the TV on in the background. It simply said "you are a prostitute, act like it and I'm sure we'll all have fun, I saw this under your favorites." She wasn't sure about who the "we" was, but it made his cock hard against his panties, and having to tuck it back was putting some strain on it. At the moment there was a knock on the door. "Who is it?" she asked somewhat feebly due to nerves.
"It's the police miss, please open the door." Kelly said, making her voice sound huskier, Trisha was trying not to laugh at her attempt, but managed to keep her composure.
Holly cracked the door open, and said "Hello, is there something wrong?"
Kelly put her hand on the door and pushed it open "I'm Officer Cox, and this is Officer Parter, we have a warrant to put you under arrest for prostitution" she was very imposing in her outfit, towering over Holly as she grabbed her, pushing her against the wall, and read her the Miranda rights. Trisha was standing back a few feet, watching Kelly take control, making Holly spread her legs and then begin to pat her down. Kelly's hands lingered on her thighs and ass, reaching under the short skirt and giving special attention to Holly's new chest. She took her hands and cuffed her behind her back, then leaned in to her ear, whispering "they're going to have a lot of fun with you in jail, you little slut."
"Please Officer, I can't go to jail, can't we work something out?" Holly sounded genuinely scared, and Trisha was a little worried until she noticed that Holly's hands were rubbing Kelly front mid-section, and attempting to move down to her crotch.
"Officer Parter, do you think we can make a deal with this little slut?" Kelly turned her head to the side and licked her lips at Trisha.
She walked toward them, and took position behind Holly, repeating what Kelly had done, then leaning forward and whispering in Holly's ear "If you're out little slut tonight, and whenever we want you I'm sure we could overlook some of your other transgressions." She flicked her tongue over Holly's ear lobe when she finished.
"I can do that Officer Parter" Holly's hands moved to the Officer's crotch, rubbing up and down. "I would be much more fun for both of you if you un-cuffed me though."
"Nice try slut, but you're staying in those unless you are a very good girl, understand?"
"Yes Officer," Holly responded, in a breathy voice, attempting to sound more feminine.
"Do you want her first Office Parter?" Kelly asked, now sitting on the bed.
"I thought you could have her first, you were the one who cuffed her after all."
"Thank you, bring her over here" Kelly stood up, and grabbed a hold of Holly, and kissed her on the lips, her tongue forcing its way into her mouth, she got rid of her sunglasses, tossing them to her partner, she led Holly in front of a chair and pushed her down onto her knees, her hands still cuffed. Kelly stood in front of her, undoing her belt, and her fly, letting her pants fall down some, and then undoing the sheath, which let her strap on spring up. "Like what you see slut?" Holly looked down on the floor, Kelly grabbed her hair "I asked you a question."
"Yes Officer, I do like it," Trisha saw her boyfriend totally submissive to her friend, and it was getting her turned on, she was sitting on the bed, and had began to start playing with her breasts subconsciously. Kelly sat in the chair, her legs spread wide, she grabbed Holly's hair again, and pulled her head onto the strap on. Holly hesitated for a second, realizing that this was no longer a fantasy, but a reality, and in that brief second Holden came back to the forefront, and he chose to give in, putting his mouth around the strap on and moved down further onto it, taking a few inches in. Kelly's hand began pushing her head farther down on it until eventually her red lips were against the base of it, and the tip was into her throat. She began bobbing her head up and down on it, moving faster and faster as Kelly began to moan as the friction of the motion rubbed against her pussy, getting her closer and closer to orgasm. Kelly screamed and moaned with delight very loudly, and she looked at Trisha, attempting to put on more of a show for her, licking her lips.
"You're little slut is quite the performer Trish, I wish we would have done this much, much sooner."
"Me too, mind if I join you?" Trisha said. Her hand been between her legs, trying to recreate the motion that and friction that Kelly was feeling. Trisha moved next to the chair, and grabbed Holly's hair, pulling her head over to her strap on, there was no hesitation from Holly this time, she went down on it immediately. She began sucking the length of it, taking it all into her mouth, moving back and forth faster and faster. "You've learned so quickly Holly, I never realized that you had all the skills of a whore in that pretty little head of yours." Kelly had gone into the bathroom, and emerged with a bottle of lube, which she was squirting on her hand, after throwing the bottle on the bed and stroking her cock, getting it nice and lubed as she moved behind the cock sucking Holly, who was totally oblivious. Kelly lifted her skirt, which let Holly know of her position, and her legs were spread as the slit in her panties was spread, and she felt the head of the cock against her asshole.
"I'm glad I'll be the first to take your pussy, I hate having to put up with sloppy seconds," Kelly whispered into Holly's ear, causing her to laugh a little, the same with Trish, which broke up her streak of moaning as she came closer and closer to having an orgasm from a blow job. She could see Holly's eyes widen as she felt the dildo enter her slowly, the first time that she was penetrated like that. Kelly continued to whisper into Holly's ear, but Trisha was unable to discern what was being said. Kelly looked into her eyes every few seconds, and licked the earlobe seductively for Trisha to see. The strap on was now fully into Holly's pussy, with Kelly nibbling on her earlobe, slowly pulling an inch or two out before pushing it back in, letting it get used to being filled, as it loosened up she thrusted harder and faster until she was at full speed. Trisha kept her mouth on the cock, as she was moaning louder and louder, one hand on Holly's head, and the other was up on her breasts, rubbing and fondling them. Then she got put over the edge, cumming from the friction.
"You're such a good cocksucker Holly," She yelled at the top of her lungs, she moved back a step and sat on the bed, then laying down as she was spent and trying to recover.
"Such a good little slut," Kelly said, as one hand moved from holding Holly's hip to moving in front where her cock would have been, rubbing up and down. "Is your little clit hard slut?"
"Yes Officer it is." Kelly began thrusting harder, and pushed her, her head moving down and laying on the floor as the thrusts continued her cheek sliding against the carpet with every thrust, back and forth. Trisha was watching, and blew a kiss to her boyfriend, who was now moaning loudly at being fucked from behind, Kelly going full speed as hard as she could, moaning loudly herself until the pleasure became too much for her to hold off and she came hard, thrusting hard into Holly's pussy, and leaving it fully in while she leaned over onto Holly, attempting to regain her composure. After a minute she got up and pulled herself out of Holly, who let out a moan from being left empty. Kelly brought her up to the bed, where the three of them laid next to each other and rested.