The Road Trip free porn video

The Road Trip Jimmy was waiting by the door of his parent's house with a small bag packed beside him. He was back from college and had spent Christmas with the family but now he was waiting on his girl-friend to come and pick him up. They were going to take a long weekend and do a little road trip for New Year's. First stop was going to be Austin. He saw her car pulling up in front. "See you in a couple days!" he hollered as he reached for the doorknob. "Have a good time, but not too good a time," his mother called back. He rushed out the door and then slowed as he spotted there were already two people in the car. He walked to the back and the trunk lid popped open. He tossed in his bag and walked to the passenger door. It was a two-door so there wasn't any question where he was going to get in. Zoe was a bit of a control freak and insisted on driving all the time, he had gotten used to that. He pulled the door open. "Hey Jimmy," Zoe called from behind the wheel, "slide on in, there's room for all of us up front." Indeed this old sedan had a big bench seat and he slipped in. "Hope you don't mind but this is my roommate from college, Karen. Karen, this is Jimmy." "Hi Jimmy," she smiled. "Hope you don't mind me coming along." "Oh, no, not at all," he immediately answered though he felt his heart sink expecting to get a little alone time with Zoe in a hotel room for a change rather than the back seat. "Karen didn't have anywhere to go over the holidays, I was just able to talk her into this trip at the last minute." "It's cool," Jimmy settled into the seat. "The more the merrier." "We've got two rooms reserved down in Austin," Zoe continued. "My father set them up. He expects the girls to be staying in one, and you in the other but it doesn't have to work out that way." "Well, let's get going!" Jimmy grinned. The girl's laughed and they started the drive to the state capital. Though Jimmy and Karen hadn't met they knew a lot about each other since Zoe often spoke to them of the other. Before they even made it to the Interstate they were chatting like old friends. Jimmy tried to take a look at Karen without being noticed. Zoe was pretty, but she was always real laid back. She wore jeans and scoop-neck tees most of the time. Her hair was brown and long, she preferred a straight natural look and hardly ever wore any make-up. Karen was different. She was shorter, and though she was also in jeans he could see enough to know they were cut to fit her very tight. She wore a buttoned blouse in a very pale pink. She wore some make-up and her hair was blond, slightly curled and just past her shoulder. Even his hair was longer than hers. They reached Austin and got checked into the hotel, Jimmy toted all the bags up to the rooms. The rooms were connected with a pass-thru door. Jimmy dropped the bags and Karen immediately grabbed a small suitcase and garment bag and hauled them through the pass-thru to the other room. "We are just staying here the one night," Zoe called to her. "Don't get too comfortable." "OK, just want to get this dress hung up for the party tonight," Karen called back. "What are we going to do before the party?" "Thought we'd just do a little sight-seeing, then come back, change for the party, grab dinner in the hotel here, go to the party, then crash for the night," Zoe answered. "Works for me," Karen answered. "Me too," Jimmy finally chimed in. Zoe smiled and went to him. "Don't worry," she kissed him long and deep, "I'll be giving you plenty of attention." Jimmy took a few things from his bag and set up an area in the bathroom. He pulled a pair of slacks and a white shirt out and hung them. Zoe finished up her chores and called out, "Come on, let's get going or we aren't going to see anything except the inside of this hotel." Karen came back through and they trouped back down and out to the car. They wandered the Capitol building, the mall, and walked a bit of the main drag before the chill drove them back to the car. Karen did stop at a liquor store and picked up a bottle of Champaign for a private celebration back in the room after the party. They got back to the rooms and proceeded to get ready for the evening. Karen went to her room and closed the doors joining the rooms. Zoe went to the bathroom and Jimmy began stripping off his clothes there beside the bed. Jimmy was clad only in his boxers as he went to the closet to get his clothes. He looked in the bathroom and saw Zoe in her panties and bra doing a little bit of make-up in the mirror. It immediately got him excited. He decided to stop in and see if he could get some quick action. "Don't even think about it," Zoe stopped applying the mascara just long enough to warn him off. "I don't do this very often and I don't want to mess it up. Karen will be ready soon and I don't want her coming back in and we aren't ready. Go get dressed." Jimmy turned away and realized he was no longer in the mood for any action. "Wonder if this is what it is like when you're married," he thought to himself. He put on the shirt, buttoned it up to the next to top button, he wasn't wearing a tie, hated that. Then grabbed the slacks and pulled them on. Belt, socks, shoes. He was ready to go. A few minutes later Zoe emerged from the bathroom. She was wearing a silk blouse with black slacks. She was also wearing a high heel which was different for her. A short time later, Karen pulled open the door between the rooms and came in. She was wearing a black dress, not formal, but nice enough for this hotel party. She had done her make-up and looked much older than she had an hour before. She also had high-heels on. Jimmy gaped, caught himself, and thrust his hands in his pockets to hide the other reaction Karen had given him. "I knew you'd make us look like slobs," Zoe teased. "I don't get to do things like this very often," Karen defended herself. "And you both look very nice. I am probably way over-dressed." "Only one way to find out," Jimmy added, "let's go." He grabbed a room key and dropped it in his pocket. They had a nice dinner in the restaurant. Zoe picked up the tab curtesy of her father's credit card, then they proceeded to the club for the party. It wasn't all that entertaining. The music was pretty lame in their opinion, there weren't any real interesting people except themselves. The only real entertainment was the view of the city from the club which was on the top floor. They hung out for as long as they could stand it and decided to ring in the New Year back in their rooms. "Good thing I got that bottle," Zoe huffed as they rode the elevator down to their floor. They went into the room, both girls immediately kicked off their shoes while Jimmy went back out to the ice machine. He returned to find both girls sitting on the bed, TV tuned to a local station working the countdown to midnight. "Should we let this chill for a bit first?" Jimmy asked. "Might not hurt, just for a few minutes," Zoe agreed. "We have about 20 minutes, let's let it chill for about 15 and then we'll get ready for the midnight toast." Jimmy thrust the bottle down into the ice bucket then joined he girls on the bed. They each moved toward the edges putting Jimmy in the middle. Karen carefully pulled her dress down as she slid across. They watched the show and talked about the next day. "I think we go out toward Fredericksburg, then cut south down through the hill country, find a place to stay in San Antonio tomorrow night," Zoe suggested. Jimmy and Karen both agreed it sounded like a good plan. Jimmy pried himself out from between them, pulled the bottle from the ice and proceeded to open the bottle. The cork came out with a gentle pop, he didn't let it go shooting across the room for fear of breaking something. He filled three glasses with the fizzing amber liquid and handed each of the girls a glass. Then with his own glass in hand, he carefully crawled back in between them. The countdown on the TV was down to 15 and when it reached 10 they began counting down together. "3...2...1...Happy New Year!" they cried out in unison, clinked their glasses together and sipped at their champagne. Jimmy turned and took Zoe and kissed her lustily. "Happy New Year," he whispered and pecked her lips again. "Happy New Year," she grinned and took another sip. "You need to give Karen a kiss." "Huh," Jimmy was stunned. "It's ok, he doesn't have to," Karen answered and took another swallow of her drink. "Do you not want him to?" Zoe leaned past Jimmy and asked. "I will not force him to or you to, but it's New Year's and everybody should get a kiss." "OK," Karen nodded and took another sip. Jimmy couldn't believe it. He turned and leaned in and briefly kissed Karen on the mouth. Not long, enough to feel the stickiness from her lipstick and withdrew. "Thanks," Karen answered, blushed a little, and took another sip. "That was nice, Happy New Year." Jimmy leaned back feeling pretty good. He had gotten a second kiss on New Year from a pretty girl at his girl-friend's insistence. "Seriously?" Zoe frowned. "You are happy with that? That wasn't a kiss. That was barely something you get from a family member. Jimmy, I know you can do better than that. I think she deserves to have her toes curl up. When she goes to bed tonight she should be thinking about that kiss. Now, try again." Jimmy was stunned. He looked over at Karen who looked equally stunned, but she also licked at her lips in preparation. Jimmy looked back at Zoe who tilted her head at him in a "Go on" type of signal. Jimmy again licked his own lips and turned back to Karen. Karen pushed herself up a little on the bed and waited. Jimmy leaned toward her, wrapped an arm around her waist, leaned further and met her lips. He pressed in, let them part a bit and touched her lips with his tongue. Her lips parted and he pressed forward. The kiss lasted several seconds and finally ended. "There, now that was a proper kiss," Zoe announced. "Um," Karen cleared her throat, "yes, it was. And I think it is time I go to bed. Thank you, both, for a wonderful evening." "Hey, Karen," Zoe called as Karen headed toward the door. "You ok?" "I'm great," Karen grinned back. "I just think you two need some time together alone now." She pushed the door closed behind her. "Alone works for me," Jimmy rolled off the bed. Grabbed the bottle and refilled both their glasses. He stripped down naked and crawled back onto the bed beside Zoe. He snuggled close and began kissing her neck. "Why," kiss, "don't", kiss, "you", kiss, "get", kiss, "your", kiss, "clothes", kiss, "off." "I need to tell you something," Zoe answered but didn't pull away. Jimmy stopped. He wondered if the kiss was a way of telling him to move on, she was breaking it off. It would be the sort of thing she would do, think she could control him going off with someone else so she wouldn't feel too guilty. "I started my period," she explained. Jimmy immediately felt crappy about what he initially thought. Then realized the cozy hotel night wasn't going to be all he had hoped. "Oh," he took a big gulp of his drink. "Sorry, but it isn't anything I can control," she answered. "But we'll have a good time on this trip anyway, and we'll get a room together another time." "Yea, sure," Jimmy agreed. He got up and refilled his glass again. The bottle was nearly empty and he was feeling a bit light-headed. He fell back on the bed, feet at the headboard, lying on his stomach, watching the party on the TV. The alcohol was stating to make him a bit braver and he started snuggling up to Zoe again. He began kissing her neck and moved to show her just how excited he was to be there. He was about to suggest she do something when there came a faint knock at the door. Zoe grabbed a pillow and threw it on top of Jimmy's bare ass. "Come in," she called. "Sorry," Karen came in wearing a white nightgown, it had ruffles and reached to just above her knees. "I can't find my glasses." She moved to the side of the bed and began looking around. Jimmy giggled and waited until he just couldn't figure out why he shouldn't help her look. He bounced up onto his hands and knees, the pillow falling to the side. He crawled to look off the side. Karen tried not to look but couldn't help herself but to peek and saw him fully at attention and quickly looked away. Flustered, she stood back up, "I don't see them, they must be somewhere back in my room, sorry." She scurried back through the door, her nightgown gently bouncing as she went. "I'm out of champagne again," Jimmy started to try and get off the bed. "I think you've had quite enough," Zoe gave him a gentle push back onto the bed. "You need to go to sleep." Jimmy struggled to think for a minute, gave up, and passed out within a couple minutes. Chapter 2 Jimmy woke the next morning feeling like a knife was lodged in his head. The room was bright with daylight, they hadn't closed the curtains far enough. Zoe was still sleeping beside him so he carefully extracted himself from the bed, grabbed up some clothes and went to the bathroom. He closed the door and turned on the shower. After a while, feeling a little more human, Jimmy came back into the room. Zoe and Karen were sitting on the bed drinking coffee. Zoe was in a t-shirt and white panties, Karen was already dressed for the day. Same as before: embroidered jeans and a nice blouse. "Good, you had clothes with you," Zoe told him. "I was afraid you were going to give us both another show." "Oh, right, I did that, didn't I?" Jimmy winced. "It's ok," Karen tried to assure him. "I didn't see much." "How could you not? He was practically waving it in your face?" Zoe laughed. "If he'd gotten up off his hands he probably would have been slapping you with it." "Stop!" Karen giggled blushing furiously. "It really wasn't that bad. I mean, yeah, I did sort of, um, see you, but I didn't have my glasses on, so..." "Please, don't go on," Jimmy begged. "I don't think this is helping." Zoe laughed again. "OK, I need to shower, can I trust you two alone?" "Is there any more champagne?" Jimmy asked. "No," Zoe answered. "Then I'm pretty sure we can be trusted," Jimmy waved her off to the bathroom. After the door closed Jimmy turned to Karen, "I'm really sorry about that, I just wasn't thinking all that clearly. Helping you look for your glasses just seemed like a good idea." "Well, I imagine you were feeling a whole lot drunk and a bit frustrated. I mean after you found out Zoe is on the rag," she explained. "Yeah, I definitely thought the evening was going to go a different direction," Jimmy admitted. They sat together in an uncomfortable silence for a while. Jimmy turned on a morning news show as a distraction. Finally, Zoe emerged and they packed up and headed out. The drove west out of Austin, did a tour of the Pedernales State Park, stopped for lunch. Walked around some stores in Fredericksburg then headed south through the winding roads of the hill country until they found themselves coming into San Antonio. The found the Alamo and El Paseo Del Rio, the Riverwalk, and spent time wandering around them until they found a Mexican restaurant they liked and had some dinner. Next up was to find a hotel. They left the area as the rooms were too expensive there and went to the outskirts in hopes of finding a cheaper but nice hotel or motel. They eventually found something they all agreed would work for a night and Zoe checked them in. "I just got us one room for the night, two beds," she told them as she maneuvered the car over to the room. "Figured there isn't going to be any action, and we've already seen everything Jimmy has to offer." "Am I ever going to live that down?" he groaned. "Not for a while," Zoe snickered. Karen giggled a bit too. Zoe parked and went to the door, Jimmy went for the luggage, Karen helped take a few things. They got inside and looked around. The room was passable, they unpacked a little of what they would need. "Jimmy," Zoe called. "You should take a shower." "I showered this morning," he protested. "Yeah, but in the morning there will be three of us trying to get ready," Karen explained. "And while Zoe and I have a routine we are used to in getting ready in the morning, you could be in the way." "OK, fine," he grabbed a clean pair of boxers and headed for the bathroom. After a few minutes, he had just gotten himself all soaped up when the door opened. The curtain slid back a little and Zoe stuck her head in. "Hey, there," she murmured. "Hey," he answered and leaned in to kiss her. They ended the kiss and Zoe ran her hand down his body getting them all soapy. "Sorry this hasn't gone the way we thought but I hope you are having a good time." While she spoke she had taken hold of him and was washing his cock and balls which was once again stiff. "Hmm, well, don't get ahead of yourself." She rinsed her hand off. Jimmy heard the door close and sighed. He thought about taking care of himself but decided to pass. He rinsed, turned off the water and pulled back the curtain. He looked around and couldn't find a towel, or any of his clothes. "Zoe!" he called. "Yes," she answered back. "There doesn't seem to any towels or clothes in here," he called. "Oh, well," she answered. "Guess you'll just have to come out naked." "What?" he felt trapped. "But last night..." "Since you've already done it then it won't be any big deal," she answered. "Is Karen out there?" he asked hoping maybe she had sent her off somewhere for something. "I'm here," Karen answered. "Oh, God," Jimmy groaned. "OK, you don't have to be naked," Zoe called back. A moment later the door cracked open and something fell to the floor. The door closed. Jimmy picked up the item and looked them over: a lacy, pink panty, and not much to them. "What is this supposed to be?" he called back. "They aren't going to cover me." "Well you have three choices," Zoe called back. "Come out naked, put on Karen's panties, or sleep in the tub. But if you sleep in the tub you'll still have to come out in the morning naked or in the panties." "These are Karen's panties?" he asked. "Yes, you know I don't wear anything like that," she called back. "But I would like to see you in them, and Karen would too." "Hey, don't make it sound like this was my idea," Karen answered. "I know but you haven't really objected, have you?" Zoe laughed. "Don't worry, this is just between the three of us. We won't tell anyone else about it." Jimmy thought about what to do. Naked would be a lot less worrisome should someone hear about it. Panties, Karen's panties, seemed awful exciting though. He leaned over, his hand shook as they held the panties while he put his legs through the holes. As he pulled them up he realized he may as well have gone out there naked. There just wasn't enough material. He looked at his butt in the mirror, the lace only seemed to add color and a pattern. He could see it clear as day. And the front? There were two little string that connected the front and back around his hips. The little triangle of pink lace held his balls and not much else. His cock stood proudly above the little pink bow. "They don't fit," Jimmy called back. "Really?" Zoe called back. "Can't get them on?" "Well, no, I can get them on," Jimmy sighed. "It's just that, well, they don't really cover me." "You got them on, though?" Zoe called. "Now you've got to come out and show us." Jimmy stood there deciding how to proceed. Should he try and use his hands to cover his manhood? Should he just walk out and pretend it didn't matter? He was wishing he had more champagne so he probably wouldn't even have thought about it. He opened the door and backed out of the bathroom. "Oh, what a cute butt!" Zoe called out. "Those panties really make you look sexy." "I have to say, for a guy you do have a cute butt. My panties do look good on you," Karen told him. "Come on now," Zoe prompted, "turn around." "But almost nothing is covered," Jimmy pleaded. "We've both seen it, turn around," Zoe purred. Jimmy took a deep breath and turned around. He held his hands behind his back. He watched as the girls both stared at him. "You weren't kidding," Zoe finally spoke, "maybe if you weren't hard you could tuck it in there, but there really isn't enough material to hide anything. And even if you did you could see everything." She looked at Karen who pulled her eyes away from Jimmy. "You really wear those?" "Yes, when I want to feel sexy," Karen answered. "Not under a short dress, I'm not that brave, but wearing sexy, lacy lingerie sometimes makes me feel really good about myself." "OK, not my style, but I like it on Jimmy," Zoe turned back to Jimmy. "Can I have my clothes now," Jimmy asked. "No, I am really enjoying this," Zoe answered. "Why don't you two play a game of backgammon or something." "Are you serious?" Jimmy asked. "Yeah, I need to do some reading and figured you could play a game or two while I do it." Jimmy looked at Karen, Karen immediately looked up to meet his eyes and shrugged. Zoe rolled off the bed, walked over to Jimmy and ran her fingers over the lace front of the panty. Jimmy shuddered. "Mmm, I do like this." Jimmy moved to the bed, Karen had backed over to one edge and was setting up the backgammon board. Jimmy had resigned himself to the situation and lay down on the bed facing Karen, his back to Zoe. They rolled a die and started the game. After a while Jimmy realized he had become more relaxed but as soon as he thought about trying to tuck himself into the panty he wore he began getting hard again. He saw Karen's eyes shift from the board to his crotch as his dick began to expand again and that just caused him to get completely hard again. She dragged her eyes back to the board, rolled double fours and declared herself the winner for the third time. "OK," Zoe announced from the other bed. "I can't handle looking at those lacy panties on his ass any longer." Jimmy sighed believing the ordeal was coming to an end. "So, I think you should play one more game," Zoe continued. "If Jimmy wins, we bring him to an orgasm that he'll never forget." "What?" Karen sat up and looked at Zoe, then back at Jimmy in her panties. "I didn't agree to that." "I know, but we've got one more night on this trip tomorrow night and I want to have a little fun, it won't hurt for you to help me. You don't have to suck him or anything. Kiss him on the mouth, maybe. Help me stroke him, if you like." Karen looked back and saw Jimmy's cock throbbing with excitement. "I can tell you he certainly likes that idea." "See," Zoe went on, "you've been looking at him so much over the last hour that you don't even think about it now. He kissed good, right? You enjoyed the New Year's kiss?" "Well," Karen looked at Jimmy, tried not to glance at his dick and failed, but nodded," yeah, it was great." "OK, you lose, I'll do most of the work, and I bet after being excited for so long today he won't last long. I'll even rinse out your panties for you if it comes to that," Zoe went on. "What happens if I win again?" Karen asked. Jimmy shuddered, the stakes were already high, he worried about what he was in for. "Well, again, I am going to ask for your help, Karen," Zoe went on. "I'd like us to do a full makeup on him. Put him in your black dress and see what kind of girl we've got." "Don't you think we've embarrassed him enough?" Karen asked. "I don't think he is that embarrassed any more about wearing your panties. And I promise, if you win, and we make you up and don't look as good as I think then I'll give you all your clothes back and I won't ever do this to you again." "Wait," Jimmy caught what she said, "what if I do look as good as you think?" "Well, let's cross that bridge when we get to it," Zoe answered. "Please, I promise, either way I'll make it up to you." Jimmy thought about it, what are the odds he'd lose four in a row. He wouldn't have on the last one if she hadn't rolled doubles at the end. And Zoe was right, he'd been pretty much naked except for the panties for a while that he really was passed the embarrassment. "If Karen agrees, then I'll do it," Jimmy announced. Karen's mouth dropped open in amazement, she was certain he would decline. "OK, my curiosity is up, let's play." They set up the board again and began the game, Zoe now was perched on the end of the bed watching intently. Jimmy was hitting well until Karen captured one of his men and put him on the rail but she only had two points covered. Jimmy's first roll was a 5-2, the two she had covered. Karen rolled back to back doubles and covered the 3 point. Jimmy rolled a 3-2 and was beginning to sweat. Without realizing he was doing it, he reached down and tucked himself into the panties, they were pinching his now soft cock. Neither of the girls missed what he did. They exchanged a glance and a smirk. Another roll and Karen was taking men from the board. Jimmy rolled and came off the rail. Karen pulled another pair off and Jimmy rolled double 2. It allowed him to get all but the straggler into the off table. Another roll and the straggler was free, double six! He raced around the board, but it was too late. He got two off and Karen got doubles again taking off the last of her men. "I don't believe it," Jimmy sat up staring at the board. "He looked at the two girls. "What are you going to do to me?" "Actually, I need Karen to do most of it," Zoe answered. "I'm not good with make-up." Karen nodded, "Come on, let's go over her by the mirror where the light is better." She pulled out a case she kept her make-up in. "Don't worry, this will be fun." She glanced down at his cock neatly tucked into her lacy panties. Karen worked away covering Jimmy's face with a base and powder, she shaded his eyelids, added mascara and thickened his lashes. "Here, let's get this on," Zoe held a black bra out and had Jimmy slip his arms through the straps. She fastened it and took loads of tissue and stuffed them in the cups that were trimmed in lace. "OK, that ought to work. Oh, Karen, you are an artist." "Thanks," Karen was seriously working now. She added more touches here and there and finally painted his lips with a pink lip gloss. "Your skin tone and hair will look great in that black dress and the shades I've used will really make everything pop." "OK," was all Jimmy could think to say. Zoe came over with Karen's black dress. "Here, let's slip this on you and be careful not to smudge your make-up." She fed the dress over Jimmy's head and tugged it down his body. She zipped up the back of it and waited for him to turn around. He slowly rotated to look at the girls. Not sure what he wanted to hear at this point he was surprised to find he actually felt good standing there in the black dress. It was tight down to his belly button, then loose down to mid-thigh where it ended. After dreading all that was being done to him he was suddenly feeling his cock trying to push its way out of his panty again. "Oh, wow," Zoe whispered. "I can't believe I've actually had sex with this person. "I know," Karen added. "I didn't think this would work when you suggested it but it is hard to believe he is a he. He makes a really pretty girl." "I'm guessing this isn't going to be the end of this," Jimmy spoke. Secretly, he was hoping this wasn't the case. "I'm afraid it is for tonight," Zoe answered. "It is already midnight. We need to get you cleaned up. But, tomorrow, I'd like to have Karen make you up again and spend the day as three girls." Jimmy looked back and forth between the two girls. He saw Karen nod. He took that as her wanting the same, and he had watched Karen transform him and had already decided he would do it. But... "I can't, shoes. I can't wear my shoes and both of yours will be too small." "Oh, right," Zoe frowned. "Well, if I can solve that, you'll do it?" Jimmy hesitated, looked at the two girls, licked at his lips and tasted the lipstick. Then he nodded. "Oh, this will be fun!" Zoe crowed. "Let me help you get out of that dress. Karen, can you help him get the make-up off?" Jimmy turned, Zoe pulled the zipper down and helped him get it off. She draped it over her arm and undid his bra then gave him a gentle shove toward the bathroom. She patted his ass as he went. "Leave the panties on, I'd like you to sleep in them tonight." She went and hung the dress up. "I guess it doesn't matter much now," Jimmy muttered as he entered the bathroom. "Are you ok with me wearing your panties?" he asked Karen as he sat on a stool. "I think it's a little late to be worrying about that, don't you think?" Karen started cleaning his face. "Do you know why this happened?" he asked. "Well, Zoe thought it would be funny to make you come out of the shower naked. I mean I didn't really see much of you last night but I saw enough, and you were pretty drunk," she explained. "When you balked she remembered these panties I had packed and grabbed them up and gave them to you. I thought you'd rather come out naked then to wear my underwear but there you were, your ass covered in pink lace." "I wasn't sure what to do," Jimmy sighed. "I even thought about just hanging out in there until she gave up, but," Karen could see his cheeks reddening as the make-up came off, "the idea of wearing those, of being yours, I just got really excited about the idea and thought I'd do it and maybe it would all be over soon." "You were," Karen giggles, "or maybe I should say still are, pretty excited about it." "Sorry," Jimmy put his hands in his lap trying to hide his cock. "A bit late for that," Karen finished up. "I think I could identify yours in a line-up if I had to. Rinse your face off and get out. I need to get ready for bed." Jimmy leaned over the sink and washed his face off. He looked up and caught Karen staring at his ass before she quickly looked away. He dried off and went back to the bedroom. Zoe was already lying in the bed under the covers. "Well, I can see nothing untoward happened in there," she grinned. "Still waving the flag." Jimmy pulled back the covers and got into bed. Karen slid over close and began running her fingers over the little bit of lace she could feel on the front. "I don't think that is such a good idea," Jimmy squirmed. "I've been ready to explode most of the evening." Karen emerged from the bathroom once again wearing her nightgown. She sat on the edge of the other bed. "Zoe, why are you doing all this to him?" she asked. "Making him get naked in front of us? Making him wear my panties?" "Well," Karen shifted her hand to above the panty and Jimmy groaned a little. "First, I didn't make him get naked, that was his doing when you came back to the room. The panties were a sort of clue I wasn't going to give in to him wanting out of the shower. I couldn't believe he actually put them on but I found out I was thrilled by it." Karen's eyes shifted down the bed where she could see the blanket moving slowly and knew what was going on. She pulled the blanket back and started to get in. "Wait," Zoe called, "how about you give Jimmy another New Year's kiss. I think he deserves a little extra attention after what we, or I, have put him through." "You aren't trying to get me involved in your sex lives, are you?" Karen asked. "Only if you want to," Karen grinned. "I've been hearing stories around the dorm from other girls. I'm curious but I won't ask you to do anything you aren't comfortable with. You don't even have to kiss him if you don't want to." "We are going to have a long talk about this tomorrow, ok?" she asked. "I'll tell you both everything tomorrow while we are on the road," Zoe promised. Karen got up and leaned over Jimmy. She pressed her lips against his, her boobs slid across his chest as she positioned herself to extend the kiss. She felt him move beneath her and realized Zoe had repositioned herself. Jimmy pushed his tongue up into Karen's mouth and felt her tongue meet his. He could feel her nipple through her nightgown against his chest and wanted to squeeze it but resisted. Then he felt he warmth on the head of his cock. Zoe had moved under the covers and was tickling his balls through the lace and was sucking on him. He reached up wrapping his arms around Karen's back. His breathing became more erratic, and he had to break off the kiss but he didn't let Karen go. "Oh!! God!!" he called out and squeezed Karen tight. Karen lost her balance and fell on top of him. She felt her hip bump Zoe's head under the covers and quickly tried to get back up. Zoe emerged from under the covers. "Wow," she laughed. "That was intense. I thought you were going to drown me. How was the kiss, Karen?" "Great for a little bit, then he got a little crazy," she brushed her hair back as she collapsed on the other bed. "Quite honestly, I was afraid he might grab something and I am not ready for that. He's your boyfriend. A kiss, ok, but, y'know, other stuff doesn't seem right." "Well, if I wasn't on my period I would probably give you a show tonight, but as it is, that was all," she laid back. "Jimmy, I think maybe you ought to take those off now. Go rinse them out in the bathroom and lay them out to dry." "Should I use soap or something?" he asked as he crawled out of bed and headed toward the bath. "Yes, please, a little bit," Karen called. A few minutes later they were all asleep. Chapter 3 Jimmy woke the next morning and stretched. He had one of the best night's sleep in a long time. He opened his eyes and spotted Karen still asleep in the other bed. "Oh, good, you're awake," Zoe called as she emerged from the bathroom. "You need to get up and get started. I'm looking forward to having a girl's day today." She grabbed Karen's leg that was sticking out from under the blanket. "You too! You know he is going to need a lot of help getting ready, I'm going to head out for a few minutes. Be back soon." And she was out the door. "What?" Karen asked in a foggy voice. "Zoe was telling me to get going for girl's day," Jimmy sat up but left a blanket and sheet draped across his lap. "I guess she is still set on doing this." "What about you?" Karen asked a bit more awake now. "You still going through with it?" "I said I would, don't know why," Jimmy snickered. "At least we aren't anywhere near anyone that might recognize me. I guess I'll get in the shower." "Do you have a razor with you?" Karen posed. "You don't have a lot of hair but you do need to clean up your neck and legs. I don't see much else." "No, I didn't bring one," Jimmy admitted, "I haven't actually had to shave yet. Late bloomer." "It's ok, you can use mine. It's pretty new so you should be ok, just go slow." "Thanks," Jimmy took a breath and stood up, quickly turned toward the bathroom and went to shower. Karen felt a little embarrassed. She could see Jimmy's dick was getting hard as he had to get up naked in front of her but she'd been looking at it almost all evening so it wasn't anything really new. She heard the shower come on and got up and went about collecting clothes for Jimmy and selecting her own outfit for the day. When the shower turned off she grabbed some lingerie and went into the bathroom. Jimmy was toweling off. "OK, so don't dry your hair," she instructed as she laid a small black pile on the vanity. Finish drying off, put on the panties and bra then we'll do your hair and make-up." She turned and left. Jimmy nodded to her back as she left. He made sure he was dry as possible then picked up the first item, the same black bra they had on him the night before. He slipped it on and found he was just able to stretch the ends down enough to fasten them together. He adjusted it to get it settled where he thought it ought to go then grabbed the other item. Black panties, bigger than the lacy ones he wore before, but these were except for some satiny ribbon accents that didn't help to hide anything. He slipped them up his legs and at least the waist was high enough that he was completely contained. They were cut very high on the hip baring a lot of skin from his hips down his thighs. He looked at himself in the mirror and could clearly see all he had to offer through the panty, but what did he really expect? At least these would be better than the pink panties for keeping him in place. He took a breath and left the bathroom. "Ah, good," Karen spoke, "much longer and we'd have to wet your hair down again. Oh, those are pretty sheer, aren't they. Sorry, I didn't notice that much when there wasn't, well, something in them. But, just so you know, those were the ones I was wearing the other night under that dress. And I guess you like that idea." She saw Jimmy's already semi-hard cock become fully erect. "Oh, sorry," Jimmy blushed and turned away, "I'm afraid I just really can't control myself." "It's ok," Karen answered. "I take it as a compliment. Now, let's get started on your hair and make-up." She spent the better part of the next hour first teasing and applying hairspray to Jimmy's hair giving it more volume and then spraying some pieces in place to make it look like a more feminine cut without actually having to cut it. Then she worked her magic on his face deftly blending colors to accent cheekbones and eyes. Finally the lip gloss and she nodded. "There you go," she announced. "Let me help you with your dress." First she helped stuff his bra, then got the dress and carefully got it on him without messing up his hair or make-up. She zipped it up. "Wow," she stood back and looked. "You really do look amazing as a girl. You could walk through our dorm right now and nobody would think you didn't belong there." "Thanks," Jimmy turned and looked at himself in the mirror. "It's all thanks to you. Makes me wonder about what you girls really look like when we meet you." Karen laughed, "Yeah, I guess you are really getting the crash course here. Of course there are some that don't do all this, like Zoe. With her what you see is what you get." "At least physically," Jimmy frowned. "I still wonder why she has me doing this. Hell, I'm still wondering why I'm doing this." "I think because you are enjoying it," Karen answered. "It's ok, you're curious and maybe this is a one-time thing. Maybe you'll want to do it more. That's up to you. I think you are pretty amazing doing it. I need to get ready or Zoe may make me go out without any make-up or having showered." Jimmy watched her go and then turned to look at himself again. He felt up his fake boobs, walked around feeling the dress slip against his legs, the hem tap against the backs of his thighs. He was trying to figure out what to do when he heard the lock turn and Zoe came back in carrying a bag. "Wow, you look great," she walked over and kissed him. "Hmm, never kissed someone wearing lipstick before, that was interesting. Here, try these." She pulled a pair of flats from the bag. He sat on a chair and slipped them on his feet, they fit pretty well, just a little tight on the sides. "They work ok," he told her and stood back up. "Good, heels would be better but we are going to be doing some walking around and there isn't time to get you used to walking in them," Zoe explained. "Also, the temp outside has dropped some so I got you a jacket." She handed it to him and he slipped it on. "I know it is short but it was on sale and besides, I want to be able to see you in the dress rather than a long coat." Karen came out of the bathroom, "Oh, you're back. I'll be ready in about thirty. Just need to do my make-up and finish getting dressed." They watched as Zoe went and pulled some clothes from her bags, she was wearing the pink lacy panties and a white bra. "Something happen while I was gone?" Zoe asked. "Nothing at all," Karen turned to face them. The bra was solid but they could easily see a patch of soft blond curls crushed inside the lacy panty. "I just decided that since this is going to be girls day I would act like it's just us girls." "OK, I'm certain he appreciates that," Zoe grinned. "Uh, yes, true," Karen answered and pulled on a pair of dressy black slacks. She then pulled on a white blouse and began buttoning it up. "But, I think you need to change, he is too dressed up for you to be running around in jeans and a t-shirt." "Oh, ok, I guess you're right," Zoe admitted. "I'll be out in a minute," Karen went to the bathroom. "Well, she certainly decided to open up some," Zoe stared at the empty space where Karen had been standing. She turned and went and found her own dress slacks and blouse and proceeded to change. Karen came back out of the bath, "Sorry I don't have a dress to wear too, I only brought the one and didn't expect to be lending it out. When I'd go out with my girlfriends in High School we'd often coordinate what we'd wear. I was always more comfortable dressed in the same sort of style as the other girls." "No problem," Jimmy answered, "I appreciate you lending it to me." They grabbed the girl's stuff, Jimmy's was already back in the car from the night before, and left the room. A cold breeze grabbed at Jimmy's dress and he grabbed it to prevent it blowing up too far. "Good grief! That's cold!" he called out. The girls laughed. Karen took the middle of the bench seat. Jimmy at the passenger window, Zoe drove, of course. They traveled a short distance and pulled up to a 7-11 near the gas pumps. "Jimmy, hate to ask, but would you mind pumping the gas? Karen and I will go in and pay and get some things." "I guess," he climbed out of the car and moved back to the pump trying to shelter himself from the wind. Zoe and Karen quickly trotted into the store and within a few seconds he got the pump going. The handle was broken and he found himself holding the handle with one hand and his dress with the other. At last it clicked off and he hung the handle up and got back into the car out of the wind. The girls came out of the store and Jimmy pushed open the doors on both sides again finding the breeze's icy fingers tickling its way up his dress. It lasted only a few moments since the girls were also trying to get out of the cold as well. "We have coffee, and egg sandwich, your choice sausage or bacon, and a little something else for you," Zoe told him as she got the car started. "Sausage," Jimmy answered and with dread, "what else have you got for me?" "These," Karen answered and handed him a package. "They'll help keep your legs a little warmer." Jimmy looked at the package marked nude, sheer to toe. He pulled the contents out and held up the beige pantyhose. "These will fit me? They don't look like they'd fit a three year old." "You'll be surprised how stretchy they are, just be careful not to put a run in them. Do it like this," Karen instructed and showed him how to gather one leg onto his fingers. "Then put your foot in there and pull it up a little ways, then get the other foot going, work it up some on each leg to the top." "Better wait," Zoe told him," I'm going to move away so nobody will walk by while you are pulling them up and see what's hiding in your panties." She moved the car away from the pumps and the store and Jimmy went to work getting the pantyhose on. He was amazed at how they fit all the way up and pulled the waistband up above his belly button. Then he quickly pulled his dress back down covering himself again. "Pretty sexy panties," Zoe commented. "I like them on you." "Thanks," Jimmy answered not knowing what else to say. He ran his hands down his legs taking in the silky feel of the nylon on his legs. Zoe pulled out of the lot and they began their journey back up I-35 toward Austin again. They ate their breakfast, and chatted. Zoe said she would get into why she was doing it later, they would be making stops along the way and just wanted to take in girl's day for a while. They stopped in San Marcos and walked around a couple places. Jimmy found the pantyhose helped some but weren't a perfect solution. Sometimes he would see the three of them in the reflection of a window, or a mirror in a display of a furniture store. It looked like three girls on an outing. He was also surprised how relaxed he was. He caught himself wondering if it were summer if he could wear a shorter dress. They drove further up to New Braunfels where they found a nice little restaurant for lunch. Zoe ordered for all three so nobody would wonder why the one girl wouldn't talk to the waitress. Jimmy found himself needing to go to the bathroom so Zoe accompanied him to help avoid any issues. He was able to get in and out fairly well, just having to fight with his dress getting caught up in his pantyhose, but at least he caught it before leaving the stall. They continued the drive and decided to make that night's stop in Waco. They thought they could go to a few places before heading back to drop Jimmy off the next day. "So, check in somewhere and order a pizza? Or find a restaurant?" Zoe asked. "Oh, I think we may have subjected Jimmy to enough and ought to head right to the hotel," Karen suggested. "Actually," Jimmy interrupted, "I've had a wonderful time today. I'd like a nice dinner for our last night on the road." Both girls looked at him with raised eyebrows. "And if it isn't too crowded, would you tell us why you've done all this?" Jimmy asked Zoe. "Yeah," Zoe smiled, "I can do that." They drove around and found a restaurant that looked pretty nice, had just a few cars in the lot being fairly late. They went in and got seated right away, Zoe requested a table away from the other few patrons. Jimmy slipped into the booth holding his skirt as he slid along the bench. "I'd have to say, you've really taken to your role as a girl today," Zoe pointed out. "The way you are doing things now just looks so natural on you." "I agree," Karen added, "I kept forgetting you are her boyfriend. Then I'd get a vision of you pulling on those pantyhose, and well, that image was gone." They all laughed. "I just really started feeling comfortable," Jimmy confessed. "I mean, I'd see us in a reflection and I couldn't tell from looking that it wasn't just a group of girls. So I watched, and I tried to mimic doing things in how you did them." "You just sat in a booth and checked your skirt as you went," Karen pointed out. "You didn't see either of us do that today." "OK, so maybe I was watching you a bit New Year's Eve," he admitted. "But the real question is why do I find myself sitting in a restaurant, wearing a black dress and sexy lingerie, as well as pantyhose?" "Oh, I guess it's my turn, eh?" Zoe answered. "Well, school has been very educational, especially outside class. The girls in the dorm, well, some of them are so different than the ones we knew in High School. I've gotten caught up in a few conversations and to be honest had a few offers of sex. I've declined the offers but that might have been part of the reason I've gotten Karen involved this weekend. I don't know if I wanted her to be part of sex with us, if I hadn't started my period right at the start of the trip I'm not sure which way things might have gone. I might have been satisfied with just us having sex. "Another thing a couple girls talked about was feminizing their boyfriends. Make them dress up, but everything they talked about was in private. They'd make them put on a dress and maybe some make-up. Then they'd make out. I'll spare you the details there but it sounded interesting. One of the girls said doing that made her curious about making out with a real girl, and so she did and enjoyed it. I think you have to want something like that anyway if you are going to start making out with other girls. "Anyway, Karen, you're my best friend, I thought if I were going to try something with another girl I wanted it to be you. I guess I should have talked to you about it first. Things just seemed to accelerate that first night. I saw Jimmy crawling around naked in front of you and wondered if you were interested in him and what if we were doing things to him together, would I get the courage to touch you?" "Oh," Karen took a drink of water, "I mean Jimmy is a good looking guy, and he certainly is, um, well equipped, but he is your boyfriend. What if something were to go wrong and then we end up being mad at each other. I don't want to risk that. You are too good a friend." "I'm sorry," Zoe reached and held a hand of each of them. "But thank you both for not just walking out on me." "Well," Jimmy spoke up, "you do have the car, and I can't exactly hitchhike like this." "Asshole," Zoe pushed his hand away and laughed. They finished their dinner and checked into a hotel. Zoe helped Jimmy out of his dress and undid his bra while Karen changed in the bathroom. She turned him around to face her and traced her fingers along the red lines in his skin from the bra. "Thank you again. This has really been fun, and I promise I won't share this with anyone at school so you don't have to worry about visiting and someone knowing." "Thank you," Jimmy pulled her close and kissed her. "That makes me feel better, but I have a question for you." "What?" "Do you think we might do something like this again?" he blushed. "I really enjoyed walking around as one of the girls. But, I'd like to maybe do it when the weather is a lot warmer." "Are you serious?" Zoe asked. "Serious about what?" Karen asked as she came back into the room once again in her white nightgown. "He asked if he could do this again, when it's warmer," Zoe told her. "Oh, I'm sorry, did you mean for that to be just between us?" "It's ok," Jimmy answered. "Karen has been a part of all this. If she wanted to be part of it again, I wouldn't mind. Besides, she knows how to do my make-up. I'm not so certain you could." "Well that hurts," Zoe huffed, "probably true, but it still hurts." "Actually," Karen added, "I think I'd like that. I had a lot of fun on this whole trip but today was the cherry on top." "Oh," Jimmy pealed the pantyhose off his legs, then asked, "should I rinse these out? Wear them to bed?" "Might as well wear them to bed," Karen conceded. "Wash your face real well like last night. You can get back into your own clothes tomorrow." Epilog They were strolling down a path alongside a park by a lake. There were stores along the street to the other side. School had let out a couple weeks before and they finally found time to get together and enjoy the beautiful summer weather. "I really like that skirt," Karen commented. "Thanks," Jimmy said and fingered the top tier. "Zoe helped me shop for an outfit for today. I just really like the layered look and she liked this skirt on me as well." "I can't believe you got her in a dress," Karen teased Zoe. "Hey, I am a girl," Zoe protested. "I may not dress all that feminine often but I can if I want. Apparently being a girl isn't a requirement but wearing a dress as a girl isn't a requirement either." "Nobody said you had to wear a dress today," Jimmy stated. "I was looking forward to doing it again, especially on a nice day where I could get a little sun on these legs." "No pantyhose this time," Karen prodded. "No, but I did wear out the others," Jimmy admitted. "I found that I liked wearing them under my jeans to class during the winter. I just had to be real careful about when I put them on or took them off to be sure nobody caught me. I wore them several times until several runs made them unwearable." "Why didn't you go buy some more?" Karen asked. "Oh, you should have seen him shopping with me to get his dress and shoes. He was a nervous wreck," Zoe explained. "I do like the shoes too," Karen commented. "I nice wedge is casual enough for that dress. And you know if we went shopping right now you could walk into any store, buy anything, and nobody would even look twice, except maybe to admire your legs. It still ticks me off how good you look as a girl." "That's just because of the amazing job you do on my make-up," Jimmy deflected. "Oh, look, an ice cream store," Zoe called out. "I'd love a cone, how about you two?" They nodded and they all crossed the street. "I'm going for Rocky Road," Zoe announced. "What about you, Karen?" "Strawberry, for sure," she answered. "Jenny?" Zoe asked. "Has to be chocolate chip," Jimmy answered softly. Jimmy reached into his purse and paid cash for the cones and they all headed for the door. Jimmy saw a reflection of the teenage boy behind the counter in a mirror staring at the three of them as they left. "By the way," Karen started when they were back outside, "what made you decide on the name Jenny?" "I was going to go for Kimmy, one letter different, at first," he explained, "but it just didn't fit for some reason. Then I tried some completely different, like Gloria, Betty, Theresa, but nothing stuck. Then after I bought this dress I put it on and looked in the mirror and said Jenny. It felt right." Karen nodded. "So, road trip?" Zoe asked. "Maybe head out to Oklahoma, or Louisiana this time? Still going to be in one room though." "Jimmy or Jenny?" Karen asked. "I thought it might be like last time," Jenny answered. "Jimmy will do the first day, then Jenny until the last day. Perhaps you could teach me how to do my own make-up so I don't have to tie you up." "Hmm, tying her up," Zoe mused. "No!" Karen snapped and gave Zoe a playful shove. "I told you I am not joining in." They all laughed. "Well, it will be interesting," Zoe went on. "Wait til you see some of the panties Jenny likes to wear. She obviously likes the sexier side of lingerie." "Don't worry," Jenny added, "I'll pack a nightgown so you don't have to look at me walking around in my underwear." "Wasn't worried," Karen answered. "Kinda got used to seeing you during that trip. That's why that last day I walked out in my own underwear. It felt like a girl's trip even if you were packing in your panties. Jenny choked on her ice cream and the other girls laughed. "I think we're in for a fun summer," Zoe answered. The girls continued to chat and stroll around the lake enjoying the sunshine and some girl talk.