tagIllustratedHolly's Night Out

Holly's Night Out


Thanks to FallenangelsSlut for the idea for this story, as well as the pics. Also thanks to Fallenangel3 for allowing me to use her pics.


Since Tricia and her friend first fed Holden's fantasy of dressing their relationship had totally changed. Holden would turn into Holly almost daily now, and Tricia loved it. She could take her out shopping and they had accumulated a fairly large wardrobe since Holly and Tricia were about the same size. Tricia loved Holden, and she loved even more how happy he was being Holly.

Tricia drove home from work and she was a little later than usual, so she called to tell Holly that she would be home soon.

"Hello" Holly said at answering the phone.

"It's me; I was just calling to let you know that I am running late and that I'll be home in a few minutes."

"Ok, I'll keep dinner warm for you," Holly said, she was trying to make her voice sound more feminine, and Tricia was surprised at how well her voice sounded when she tried to sound like a woman.

"I love you" Tricia said, as she changed lines so she could exit off of the highway.

"I love you too," Holly said as she began to rush toward the bedroom, realizing that with the extra time she could prepare a little surprise.

As Tricia walked up to the front door she had been even later due to a bad traffic. She was frustrated, but was happy just to be home to her little housewife. She giggled after thinking that, reminiscing about how far Holly had come along. She opened the door and walked in and saw dinner on the table, and standing next to the table in a beautiful French Maid outfit was Holly. It was black and had lots of white lace trim, it clung to her figure very closely, giving her womanly curves. Her legs were encased in white fishnets, and she wore 4" high black heels. She went for a blonde wig, and light make up, except for bright red lipstick.

"Bonjour, dinner is ready." Holly said and smiled at Tricia, and walked over to her, giving her a kiss. Tricia grabbed her head as she tried to pull back, and moved her tongue into Holly's mouth and began to make out in the dining room until Tricia broke the kiss "sorry, but I don't want dinner to be cold."

"OK," Tricia said as they both sat down and began eating. "Where did you get that sexy outfit?" she said between taking bites.

"Just a little costume shop I found a few days ago, it's called Trudy's"

"I'll have to go with you sometime, pick out a few more outfits for you." They both smiled and finished the meal talking about their days. "Can I have dessert?" Tricia asked, biting her lip

"Of course," Holly responded, and moved her chair to the side, pulling the skirt and the few petticoats up, revealing some lacy black panties that were doing their best to restrain her rock hard cock, but were failing as it grew harder and harder. Tricia got down on her knees and released it, wrapping her hand around it. She started jerking it slowly, licking it up and down to get it nice and wet, and then she kissed the head and opened her lips, letting it slide into her mouth, her lips going all the way down the shaft, then bobbing her head up and down, looking up at Holly, their eyes meeting as Holly began to moan. This spurred Tricia on, her hand moving down and began to rub on Holly's waiting hole, teasing it. Holly had been hard ever since she had put on the maid outfit, especially the panties, and she couldn't hold off any longer, and she came inside of Tricia's mouth, who eagerly sucked her dry. Tricia stood back up and kissed Holly on the lips, letting her taste her own cum. "Thanks for the dessert," Tricia said, as she walked out of the kitchen "be sure to clean up."

Holden woke up the next morning and things were very normal for a Saturday, he and Tricia sat around and had breakfast while reading the newspaper, he went outside and did his weekly yard work while Tricia ran some errands and did some chores inside. Holden walked into the house, sweaty from working outside, and Tricia asked him "how much longer are you going to be out there?"

"I don't have that much left, why?" Holden responded, grabbing a bottle of water from the fridge.

"Because we're going to go out later tonight, a little surprise for you," Tricia said. Holden went back outside and got the yard work done, and came back in, got showered.

Tricia didn't mention anything else about them going out until later on, when he was sitting on the couch and she walked up to him and straddled him, putting her arms around his shoulders and neck and kissed him. "So where are we heading out to tonight?" Holden asked as his hands moved to her sides, and down to her ass.

"It's a surprise, but you can just wear what you have on now. It'll be a lot of fun, I promise."

"OK, so when do we leave?" he asked, his hands now massaging her ass in an attempt to try and get a quickie in before they had to leave.

"We should probably head out now" she said, and pulled herself away from him "but, you're going to have to wear this" and she produced a black cloth hood. "For the surprise and all."

"OK, I trust you that this will be a lot of fun," and Holden stood up, and followed her out to the car, her surprises had always led to fun before, so Holden was excited with the possibilities. She put the hood on him and had him sit in the back seat so it would look less suspicious, and drove off. While Holden was hooded he attempted to try and figure out where they were headed based on turns, how fast she was driving, but he lost track after a few minutes. After 30 minutes or so in the car it came to a stop and he heard Tricia open her door, then her walking around the car to the trunk, which opened and closed, and then she opened his door. She removed the hood and he realized that they were in front of a large home, one that he did not recognize.

"We're here," Tricia said "Can you carry this?" she asked, and Holden took the handle of an overnight bag, which had been in the trunk. Then she led Holden up to the front door, Holden was too busy looking at the house to really ask any questions, he also loved surprises, and he didn't want to ruin this one. Tricia knocked on the door nervously, she had never been to this house before either, she had found the couple on-line, they hosted a local swingers club that invited all comers, gay, lesbian, bi, whatever people may enjoy or want to try, they had it there. Tonight Holly was going to be the featured entertainment, and as the owner looked at them he thought that it could be a very good show. The head of the club was a man in his 40s named Shawn Horvath, he kept his hair parted and it was beginning to gray behind his ears. His face had begun to wrinkle, but not hiding that he was an attractive man. He was tall and lean, after gaining wealth he kept in shape by playing tennis and golf, living a life of leisure. His wife was in her late 20s, blonde, and part of Shawn's money had gone into shaping her beautiful body. They all greeted each other and Shawn led them on a quick tour of the house as they walked through a large sitting area, and to the backyard, which featured a large pool. Many of the guests had already arrived and were outside by the pool.

"What kind of party is this?" Holden asked, he saw a lot of very amorous couples by the pool, but waited to ask until they walked back inside.

"It's a swinger's party, I'm in charge of the group since the parties are at my house," Shawn replied, proud of his house. "So did you tell Holden here about the entertainment for the night?" Shawn asked, looking at Tricia.

"No, I was going to tell him once we all went upstairs," she replied, a little nervous.

"Then let's head up there," Shawn said, his wife had run off to watch a couple that was having sex in a sun chair next to the pool. "She loves to watch; she usually just runs around watching everyone else and forgets to ever participate when she sees someone she likes." They walked up a high, curling staircase and to a room that was nicely decorated, with a four post bed, a dresser, a full length mirror, and its own bathroom. "This is the main guest room, if you feel like staying the night then you can sleep here, it'll be closed off during the party. Should I tell him, or do you want to?" He asked Tricia, looking at her.

"Holden, the surprise I had for you was that I told Shawn here that we would perform for the club tonight."

"What kind of performance?" Holden asked.

"You should probably open up the bag and I think you'll see," Tricia said, getting excited from the anticipation. Holden opened the bag and saw a schoolgirl outfit. The outfit consisted of a short red and black plaid skirt, a white button up that was tied at the bottom, giving her fake breasts a boost, along with her black bra. Holly felt the white stockings in her fingers as she took them out and felt them, and on the bottom of the bag, were a pair of black high heeled shoes, the same ones she wore with the maid outfit.

"The plan was for you to be the naughty schoolgirl, I'd be your teacher" Tricia said, as she saw the smile grow on Holden's face and knew that he was getting turned on by it.

"Sounds like fun," Holden said, as he started thumbing through the schoolgirl outfit, taking it out of the bag and laying it out on the bed, keeping the black panties with the convenient slit in the back in her hands.

"I guess he's ready, I'll get everything else ready," Shawn said, looking at Tricia "It's going to be a great show," he backed out of the room, smiling at Holden. As soon as he left Tricia asked "Do you need my help with anything?"

"No, I can do all of this myself," Holden said "I've gotten very good at becoming Holly," they both smiled as he said that.

"Good, because I have to go, someone will come and get you when we are ready to start." Holden nodded and smiled at Tricia, who smiled back and then left. She went into another room across the hall to get dressed into her costume. It was a mid-thigh length black skirt with black stockings, some black high heels, a white blouse, and her hair pulled back tight into a bun. She even added some black rimmed glasses, giving her the perfect stereotypical uptight teacher look, which was exactly what she was going for.

Holly heard a knock at the door, then a female voice "Are you ready dear?"

"Yes, is it time to start?" she responded, trying her best to make her voice sound soft and feminine. The door opened and it was Shawn's wife, Emma.

"Wow, if I didn't know it I would never know that you were really a guy, you make such a sexy girl," she said, looking Holly up down, seeing her make up, and a long haired wig. "But they are waiting for you downstairs, Tricia told me to give you this." It was another of Tricia's little notes, this one read: Holly, you are a schoolgirl who is coming by because you are trying to get some extra credit in my class. I love you, and it was signed "Your favorite teacher." Holly's anticipation level grew as she concentrated on walking down the stairs in her heels, something she was not used to. As she saw the main room she noticed that the furniture was moved so that it was in a circle, and in the middle was a large desk, and in front of it was a very plan looking school desk. When she got to the bottom of the stairs everyone looked at her, she could see the men and women there ogling her, some of the women started to lick their lips in her direction, but all that could go through Holly's head was "I wonder if they know I'm really a guy under this make up and outfit?"

She got inside the circle of furniture, and then Tricia looked up at her and said "Why are you always tardy to these meeting Holly? Especially when you're the one who schedules them" She shuffled some papers on the desk and began acting like she was grading them with a red pen.

"Sorry, I have gym last period and it's difficult to get dressed again very quickly," Holly said, taking a seat in the desk. "Some of the other girls really hog the showers."

"You're just here to see me, why does it matter so much how you look?" Tricia asked, raising her eyes from the papers.

Holly wasn't sure how to respond, but she said "Well I always try to look my best, irregardless of who it is."

"It's regardless, not irregardless" the crowd laughed a little at Tricia's comment, but most of them were totally engrossed in the scene. "Too bad you don't put that same effort into your school work. I hope you realize that you are failing my class."

"Yes ma'am, I know that, I scheduled this to see if there was any extra credit I could do, I really need to pass, anything that I can do to help my grade I'll do," the crowd's interested piqued at that, as did Tricia's who stood up from her chair and walked around to the front of the desk.

"Come here Holly," Tricia said, motioning with her finger for Holly to come over. Holly got up, and tried to put her skirt down some before she walked over. She stopped a step short of Tricia, who motioned for her to come closer. Tricia grabbed her, and pulled her close, kissing her on the lips, their tongues intertwining, and Tricia's hands began to move up and down Holly's body, moving under her blouse to feel her breasts. Holly did the same to Tricia's body, leaning back to give her more access, they both paid attention to the other's ass, and Holly made sure to fondle Tricia's breasts. Tricia broke the kiss and hopped up on the desk, and hiked her skirt up on her hips, revealing that she was not wearing any underwear. Holly didn't need any prompting, and she went down onto her knees in front of her, putting her mouth at the perfect height to her girlfriend's pussy.

Her hands spread Tricia's legs, letting a few lucky viewers see her pussy lips before Holly's head moved in to block it. She plunged her tongue into Tricia's waiting pussy, tasting her juices, feeling them on her tongue and lips. Tricia was getting into the show, and she undid the bun in her hair, and flung her head around, letting her hair fly in the air, much to the enjoyment of the crowd, which cheered and whistled. Holly's hands reached up and ripped open her blouse, revealing her large tits overflowing out of a white bra. Holly was kissing back down Tricia's stomach and made her way back to her pussy, plunging her tongue deep inside again, and then moved her hand down to her pussy, pushing two fingers in, and sliding them back and forth, feeling Tricia's pussy contract around them. She was moaning loudly, laying flat on the desk, rubbing her now free tits as she ditched her bra and threw it into the crowd. Holly's tongue moved to her clit, flicking at it, then taking it between her red lips and sucking on it, which drove her partner over the edge, her hand moved to the back of Holly's head, holding her down as her body spasmed for all to see, and she moaned loudly as she came, her pussy gushing with juices that covered Holly's lips and mouth. She pulled off of her pussy, and Tricia leaned down to kiss her.

"What is going on here?" a voice boomed from the crowd. They both saw Shawn moving toward them, wearing a gray suit with glasses on.

"Principal Horvath, it's not what it looks like," Tricia said as she tried to button her shirt and flatten her skirt down. Holly froze, not knowing what to do, she was caught completely surprised.

"It looks to me like you're taking advantage of this little student of yours," he said, looking at Holly, who was still dumbstruck. "And you didn't tell me to let me in on it, you know how our little deal works," he looked back at Tricia and smiled, she smiled back.

"Well I just finished, so she is all yours now," Tricia said, as Holly realized that there was another surprise in store for her. Tricia hopped down off of the desk, went over to Shawn, kissed him on the lips "Mind if I watch?" she asked, her hand undoing his tie.

"Sure, take a seat and you can be taught a few things as well," he replied, as they broke their embrace and he moved over to Holly. "Such a sexy little schoolgirl, you do have very good taste.' Then he kissed Holly, it was the first time she had ever kissed a real man, his tongue moving its way into her mouth, she couldn't resist, she loved how it felt. His hands began roaming all over her body, lifting her skirt up and lifting her onto the desk as he moved between her legs, kissing her the entire time. He pulled her close to him, and she could feel a bulge against her. Tricia was sitting in the desk, but she moved it to one side so that she could get a better view of Holly. Shawn's mouth moved to her neck, kissing up and down, untying the knot at the bottom, and then moving down it, kissing her fake breasts through her black bra, then his hands fondled her false breasts, replacing his mouth. He then pulled back and Holly's hands moved down and started undoing his belt, undoing the button his pants as he ditched his sport coat and grabbed a condom out of his shirt pocket. Holly freed his cock from his boxers as he opened it and rolled it on. He pulled Holly off of the desk some, letting her ass slide off, and her legs went on top of his shoulders for balance. Her skirt was hiked up on her hips, his hands reached down, finding the hole in her panties, reaching underneath them to pull her ass cheeks apart, leaving her open for his cock as he pushed against her hole. Holly was moaning now, the anticipation of being penetrated by a real cock for the first time having really turned her on.

"Ready for me Holly?" Shawn asked "I'll make sure that you pass not only this class, but all your classes, and with A's, not C's."

"Yes sir, please sir," she said while breathing heavy and moaning from feeling his hands all over her body. That was all the prompting that he needed as he slowly thrust himself into Holly's waiting hole, letting her feel every inch of his 8" cock. Her head was at the desk, and she kept moaning and screaming with every thrust he made inside of her, her legs on his shoulders as he took her, the first time that a man had. He started slowly, being gentle, but realized that she was no virgin there, and so his thrusts began to take on a quicker pace, and a harder force, his body ramming into hers once his cock was in as far as it would go. He groaned as he thrusted, sweat beginning to form on his brow from the exertion, and she continued to moan and scream at how great his cock felt inside of her. Holly felt one of his hands move down to her panties, and started rubbing her restrained cock, and the combination of that and his hard thrusts into her was too much, as she moaned and moaned and came in her panties, spurting again and again. Shawn could feel her cock twitch and he grabbed her ankles, spreading her legs as he continued to thrust, pulling her closer to him, and then he thrust all the way inside of her and came. He slumped over her after he did, and after a few seconds, he kissed her again.

The crowd began to applaud and cat call at the conclusion of the scene. Shawn and Holly put their clothes back on and waved to the crowd and took a bow. Tricia ran up and kissed Holly, and since they were tired from the show they only observed the rest of the time they were at the house, and talked to the others members, who complimented them about there show, and that they'd have to perform like that again the next time they came to a party, none of them realizing who Holly really is.

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