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Three Cheers for Freedom I looked up at the clock on the wall as the second hand crept around the face of the clock. The bell would be sounding any minute and I couldn't wait to get out of class. There is one more after this but that is ok because I get to spend it with my girlfriend. The bell finally sounded and I joined the crowd of students and teachers that flowed through the hall. The din of a hundred conversations joined the clang of locker doors being opened and closed. I ignored it all and wormed my way to the classroom door down the hall. I saw the long blond hair of the back of her head as she turned away from me. She knew I would catch up quickly, it was a process we went through every day. I fell into step beside her. "Hey there," I called to her. "Miss me?" "Oh, yes," she answered with a laugh. "Those two hours since lunch were almost unbearable without you." I laughed with her. I really couldn't believe the luck I had. I didn't have a lot of friends when I started high school. A few here and there, mostly like me, somewhat out of place and always seemed to attract the attention of the bullies. I was smart, both book smart and common sense smart which don't often go together and it helped me get out of most troublesome situations. Though not terribly athletic, I could do ok in most sports. That didn't change things in Physical Education where I was almost always the last one picked for any team. I didn't really blame them on dodge ball, though. I hated that game and really tried to get eliminated early. So, one day toward the end of the sophomore year I overheard Diane talking to someone about a chemistry project she was having trouble with. Diane was one of the pretty, popular girls. She was a Junior Varsity cheerleader and everyone knew she would be on the Varsity squad the next year. Probably end up on the student council as well. Something overcame me at that moment and I actually decided to speak to her. "Excuse me," I spoke softly to her, my voice cracking with nervousness. "I didn't mean to eavesdrop but I think I know what your problem is on your project. I could help you." The girl she was speaking to stared at me. I knew she didn't think I should be allowed to address them, and I expected the same from Diane but she surprised me. "Really?" she smiled and it lit up her whole face. "I would really be so grateful. I have other projects to finish and just can't find the time to solve this." I figured she was just looking to use me to do the work, but what the hell? I would maybe get to spend an hour or two with her. If she didn't try and make me do all the work it might be fun. "Yes," I answered. "I'll bet I could get you on track in an hour or so." "OK, great," she smiled back at her friend who still regarded me as if I had climbed out of a rancid swamp. "By the way, my name is Diane. What's yours?" "I'm Zach, and everyone knows who you are." I think I blushed. "Well thank you, Zach," she reached her hand out and I shook it briefly. "When is a good time for you?" We talked for a few more minutes and arranged a time to meet after school to go over everything. It ended up taking a lot more than an hour. Once it was just the two of us we got along real well. She turned out to be a very friendly girl and open to being friends with me. We spoke often, much to the disdain of her other friends, during school until the end of that year. When we came back to start the junior year we found ourselves in a couple classes together. The first one, Algebra 2, I had gotten to first. I took a seat and when she came in she grabbed the one right beside me and started asking me about my summer! We talked until the teacher cut us off and then compared schedules on the way out the door after class was over. After Christmas break I got up the nerve to ask her out on a date, fully expecting to be turned down flat. Being friends at school was one thing, going out together, probably not going to happen. She accepted! We dated the rest of that year, went to Junior Prom together. She really boosted my self-esteem. Her friends slowly accepted me but I knew that if anything ever happened to split us up I would be dropped like a hot potato. We continued to see each other over the summer when our families were in town or she wasn't at cheerleader camp. We arranged our classes for senior year so we could be sure to share a few. She had to take Physics for the college she was applying to so I signed up for it as well. I could take anything I wanted as long as I passed at least one of them. That was where we were walking toward now. "Oh, Zach," Diane interrupted my revelry, "I found out the date of the powder puff football game. We get to play it just before Halloween." "Good deal," I nodded. "I'll be there to root you on." "I know," she hugged my arm. "You always support me. I just wish you could do more. You know we dress up the football team to be our cheerleaders for the game but they can be such jerks about it. They don't take us seriously at all." "Well, consider that you make them look foolish," I countered. "I mean hair in pigtails if they have enough, crepe paper streamers for a skirt over gym shorts, and big balloons for breasts. Not to mention the silly make-up job. They are farce personified." "Do you honestly think any of those guys would let us do a serious job on them?" she asked. "No, it would threaten their social standing too much," I acknowledged. "I, on the other hand, have nothing to lose. You are my social standing." We sat through a lecture on directional forces and gyroscopes and waited for the final bell to ring. As we left the class Diane took my arm, "Do you really mean that?" "Mean what?" I thought back. "That you would be a serious cheerleader for me?" she asked. "I'm always a serious cheerleader for you," I wrapped my arm around her waist. "I'm your biggest fan." "I want you to be a real cheerleader for me, for my team at the powder puff game. I am going to do a serious job on you if you'll let me. We'll show them that we girls can be serious about the game, and you can be serious about the cheerleading." I didn't give it much thought until the week before the game when Diane suggested I come by her house so we could be sure everything fit ok. * - * - * "Hi, mom!" Diane called as we went into her house. "Zach and I are heading up to my room." "OK, dear," she called back from another part of the house. "Will Zach be staying for dinner? It will be ready in an hour, we are having meatloaf." I nodded to Diane that I would be willing. "Yeah, he's staying," she called back as we headed toward her room. "OK, remember," she stuck her head out the kitchen into the hallway, "the bedroom door stays open." "Of course, mother," Diane sighed. "I know the rules." I just smiled at her mother. It was obvious where Diane's beauty came from. Diane went right to work pulling her uniform from the closet and comparing it to my body. It looked like it would be a decent fit. "Take your shirt off," she instructed. Nervously I pulled my t-shirt over my head. I didn't have any body hair yet. Half the guys in school shaved and I didn't see a single one that wasn't on my head. My dad tried to reassure me that it would grow in time but that it wasn't a big deal. My mom, who hadn't been around in years, had a lot of Native American in her lineage and I might not grow a lot of body hair. I also didn't have a lot of muscle. Diane looked me over for a second, it wasn't the first time she had seen me without a shirt, we had gone swimming together many times, but she was doing a different evaluation this time. She turned and went to her dresser. "Here, put this on," she handed me a white bra trimmed with lace. "Really?" I held it feeling the texture. "Serious right?" she asked. "Are you having second thoughts." I swallowed. I thought for a second and decided I was going through with it. "No, no second thoughts." I examined the item and slipped my arms through the straps. It had a front clasp between the cups which I thought would make it easier but the elastic made the ends disappear under my arms. Diane watched me struggle with it; I think she was really enjoying my dilemma. I finally managed to get hold of both end and connect them. "How's it feel?" she asked as she readjusted the straps and untwisted some of the edges that had folded over. "Tight," I answered. "Yeah, well it is supposed to be," she giggled. "We'll find something to fill it with so you have breasts." "What is going on in here?" her mother was standing at the door watching us. Now I was really embarrassed. "I told you," Diane answered. "Zach is going to be a cheerleader for us. We are working out his uniform now." "You are a brave boy, Zach," her mom shook her head. "I think I have an idea for you though. I'll be back in a minute." "This is an older bra of mine," Diane explained as we waited. "After you finish with it I'll probably toss it out. I guess since it is just you and your dad you haven't seen much of women's lingerie around the house." "Only in the Sunday ads," I admitted. I didn't want to admit that I was very excited. Diane and I had kissed but we didn't do anything else. I was afraid to ask and Diane was too afraid of disappointing her parents. "Here we go," her mom came back into the room carrying a couple clear bags of white powder. "I put flour in some freezer baggies. I think they should be the right size." Without stopping she came to me and slipped the first one into the cup giving me a left breast. She molded it into shape and satisfied went to work on my right one. When she stepped back to examine her work I was still feeling mortified. I just sat there trying to consciously reduce the heat I could feel in my face and my crotch. "I think that will work pretty well," she nodded. "Diane, hand him the sweater." Diane gave me the sweater and I dutifully pulled it on over my head. I was grateful to not be sitting there in a bra any longer. I stood up and pulled it down to my waist, my breasts were evident but not overly done. "Thanks, mom!" Diane clapped. "I think that is perfect! He won't look anything like the football dolts with breasts as big as their heads. I want him to look real." "OK, glad to be of some help," she turned to leave. "Dinner in 30 minutes." "OK," Diane answered but was already planning the next step. "Here, take these to the bathroom and put them on." She handed me more clothes. I crossed the hall, closed and locked the door. I found a white pleated skirt with red and black inside the pleats. Also a pair of red panties? Shorts? I didn't know what to call them. Cheerleader underwear that gets seen whenever they do their kicks and flips. I stripped off my pants and underwear and slipped them on. I pulled on the skirt and got it situated on my hips. My heart was racing with all the new feelings. I was aware of how the skirt slid against my legs and how open I felt behind as I stooped and retrieved my clothes from the floor. I went back across the hall to Diane. "Oh, you look great!" she cried. "This will be so much fun. So, next Friday I want you to come by here early so you can change and I am going to put some make-up on you." She walked around me checking me out. "Your sneakers should be ok, even though it seems we are the same size clothes your feet are bigger than mine but cheerleaders wear sneakers most of the time anyway. How do the pants fit?" She lifted the front of my skirt before I could react. "OH!" she let my skirt drop and I could see her blushing. "I'm sorry, I didn't realize." "I'm sorry," I apologized back. "I don't know why I'm reacting this way. I feel like I ought to be too embarrassed to be excited. Even now I can't seem to not be excited." I sat on the bed and tucked my skirt down between my thighs. "It's ok," she tried to reassure me. "I just didn't realize that it would be that obvious, even if you weren't, well, you know." I just nodded refusing to meet her eyes. She thought for a moment, went to her dresser and dug something out. "Here," she tossed me something. "Try this under the pants. It might be tight enough so you don't show that big bulge if your skirt flies up." I looked at what I had caught and it was a black thong. The front looked like it would be wide enough to hold me. I nodded still not looking. Then I realized she had said big and felt good for a moment. "You can check yourself in the mirror when you get them on," she pushed me toward the bathroom. Once again I closed the door. I reached under my skirt and removed the pants. After examining the little black thong I stepped into it and pulled it up. It was tight and I wiggled around getting it into place. It felt weird as the little strap slipped between my cheeks but once in place it really did keep me tucked in close to my body. I pulled the pants back on and raised my skirt to look in the mirror. There was still a bulge visible but nowhere near as obvious as it was. I returned to Diane's room. "Well?" she asked as I came in. "Much better," I assured her. "I think you can look this time. It wasn't like it was." Diane hesitated then decided to look. She lifted my skirt like she was afraid something was going to jump out at her, but that is exactly what we had just taken care of. Then she nodded and dropped my skirt. "OK, yes, much better." "Dinner!" came her mother's call from the kitchen. "I better change before we eat," I told Diane. "I don't want to sit at your dinner table like this and I don't want to get anything on this by accident." "Good idea," Diane headed for the door. "You can change in here, I'll tell Mom you are on the way." She closed the door as she left. I peeled off the clothes I was wearing and put my clothes back on. I put the uniform back on its hanger and hung it in the closet. I couldn't help but feel the material on a couple other things that were hanging in there as well. I went back and placed my breasts with the bra and thong in a neat pile on her bed and went and joined the family for dinner. * - * - * Friday rolled around and I got up early to shower and make sure I was squeaky clean. I headed over to Diane's with feelings of both dread and excitement. I knocked on the door and Diane's mom opened it. She hadn't really gotten started on the day yet. She wore a robe with a hint of a red nightgown peeking out through the opening. Even without make-up she looked great. "Still going through with it?" she asked as a greeting. "I guess so," I shrugged. "I don't want to let Diane down." "She's in her room waiting for you," she stepped back to let me in. "Have fun." I knocked lightly on Diane's bedroom door and heard her answer. I pushed in, my whole body was shaking. She smiled at me and it helped. "You are really special for doing this. I haven't told anyone about it so it is going to be a real surprise." She was dressed in jeans and a football jersey. She had her hair tied back in a ponytail and had done her make-up real light. She also added black on her cheekbone below her eyes to cut the glare. She looked really cute. Thing was there was going to be almost twenty other girls running around the school dressed the same. The football players would all have their rosy red cheeks, pigtails and crepe paper streamer skirts and acting like idiots. I was going to be the only legitimate cheerleader. I went to the bathroom and put on my thong, pants and skirt then returned so Diane could help me with my breasts in my bra. Once I was dressed she went to work on my face doing a serious make-up job on me. She purposely overdid the eye-shadow and lipstick to make it obvious it was a bit of a farce, but the overall effect was amazing. I wasn't going to be mistaken for a girl up close, but from a distance it might be tough to tell. I drove us to school and she kissed me carefully so not to smear my lipstick and I nervously walked to my locker while she went to the gym to help do up the football team with the rest of the cheerleaders. I showed up in my first class and took my seat. At first nobody knew what to say to me but they weren't shy about looking. I kept fidgeting with the skirt making sure it wasn't stuck up on the back of the chair or anything. I crossed my ankles and squeezed my knees together. Just as the bell rang, two of the football players came bouncing into the classroom yelling and whooping. "Everybody needs to come to the big game tonight! Come and cheer for your favorite squad!" They kicked their legs and shook their butts. Then one of them spotted me, grabbed the other and pointed. "Zach?" he asked, "what the ..." he caught himself and glanced at the teacher. "What are you doing?" "Diane's idea," I sat up and explained to everyone. "She wanted someone who understood they were serious about playing tonight and would be a serious cheerleader for her team. So, here I am." "That is totally wrong," the other one added. "I hope she is giving you something special for this. Oh wait! Everyone knows she doesn't give you anything!" They both started cracking up laughing. "That's enough boys," the teacher scolded but I could see a bit of laughter in her eyes as well. "I think you should be on your way now." Still laughing they went out the door and we could hear them yelling again as they entered the next classroom. All through class I saw both the boys and girls eying me. Nobody else offered any comments and I was able to get on to the next class. It is amazing how fast word gets around in a high school. By the time I walked into that classroom it seemed everyone already knew that I was wearing the cheerleader outfit. There were a few remarks but nothing too terrible and I took my seat. I was getting more comfortable moving around and I didn't pick at myself as much. I tucked my skirt as I sat which elicited a couple snickers but I ignored them. It was better than having my pants showing. Diane finally caught up to me third period, which we shared English. She asked how it was going and I told her it wasn't too bad. She surprised me by saying that maybe it wasn't such a good idea. Friends of hers were giving her trouble about it. I just told her we didn't have a choice any longer and I was standing by her no matter what. She gave me a little hug. We finished the day and the girls all went to the gym to change into the shorts they would be wearing for the game. I went out to the field and took a seat near the bench that would be occupied by Diane's team. When they finally emerged I jumped down onto the track that surrounded the football field and started cheering for my girl and her team. People pointed and laughed but I just ignored them. Diane's team won the game and after she gathered her clothes from the locker room we went back to her house where she helped clean all the make-up off. Diane didn't talk too much. When I prodded her about how she enjoyed playing in the game her answers were short and dismissive. I stripped off the sweater, bra and breasts then went to the bathroom to remove the skirt and all. Once I had my own pants back on I returned to her room and put my shirt on. I dropped the rest of the clothes on the pile on her bed. "Why did you do that today?" she asked quietly. "Why did you embarrass yourself like that?" "Because you asked me to," I told her. "And it wasn't that bad. A few jerks and one girl that pinched my butt when I was going up the stairs. Overall, I think they let it go because of you." "No, I don't think they did," Diane sighed. "My other friends are all saying you did it because you are really a faggot and that is why you aren't pressing me to have sex." "That is ridiculous!" I countered. "We've talked about sex and we've agreed we should wait. Did you tell them that?" "Yes, but they think I am just covering for you." "Well who cares what they think?" I answered. "You went out with me when nobody else thought you should waste your time on me. I found out not all the cheerleaders were snobby bitches. We are good together." "I guess so," she turned away from me a little. "Why were you so excited that first time you put on my clothes? Was wearing my things exciting for you?" "Well, yeah," I admitted. "I mean there haven't been clothes like that around my house. I've never really seen or touched anything like it before. And the idea that I was wearing something that you wore just got me turned on because it was like I was closer to you than I had been before. And the way they feel when I was moving around. Don't you get excited by them?" "No, not really," she shook her head. "I guess since I grew up wearing dresses and stuff it is just normal to me." "OK," I reached to hug her. "I guess that makes sense." She let me pull her close but kept her arms crossed over her chest keeping a distance between us. I kissed her and left. * - * - * We met up again on Monday and talked some more. Things were different though. I didn't understand. This was her idea; she didn't have the problem with it her friends did. It didn't matter though. Over the next couple months she pulled away from me. She would still say hi but that was about it. I could see the same look in her friend's eyes that said I wasn't supposed to be talking to her any more. High school sucks. We got through the end of the school year. She had gotten into a college with her best girlfriend. I ended up at a college in the completely opposite direction so I guess it was just as well that we weren't together any longer. Working out a relationship with all the new things that college offers would be a rough time. * - * - * I got to college and was looking forward to the new experience. I thought that now that I was among an older crowd that the maturity level would be so much better than it was in high school. It didn't take long before I discovered that it wasn't really that much different at all. With the new found freedom of being away from home lots of the kids were drinking and having sex whenever they found the time. The cliques that were in high school once again developed here. I thought I found a way to beat that because I got an invitation to come to a pledge party for one of the fraternities. It seemed like a great way to get into a crowd if I could get accepted, though it seemed like I was volunteering myself to the school bullies to be humiliated. Despite how things had ended between Diane and me I had developed a better sense of myself. I had a bit more confidence, plus when I signed up for the fall semester I didn't see dodge ball on the class list anywhere so I was sure I wouldn't end up in a class that I was afraid of. I was also surprised that I was able to make friends outside the frat group easily as well. There were a few in my Introduction to Computing class that I got along with, guys and girls both. And my chemistry lab partner was a nice girl, Pam, that I got along with terrifically. She was pretty, not as pretty as Diane, but more than pretty enough for anyone I knew. She was more like a girl next door than the cover to Teen People or something. I was staying busy between the pledge tasks that we were assigned; some of it was really stupid I thought, but they insisted that going through this would make us a tighter group. I worked a campus job to earn a few dollars for my pocket. My studies ate up the rest of my time. We were nearing the end of the pledging when they announced we would all be attending a party with our sister sorority. The entire pledge class was required to attend and required to wear a dress or skirt. It felt like the blood in my veins turned to ice water when I heard it. Yeah, I had enjoyed it the last time, but the results were that I had lost my girlfriend and ended up feeling ostracized for the rest of my senior year. I went to the chemistry lab the next Monday and told Pam about the upcoming party. Pam was a sophomore so had been around a year longer that I had. "Oh, yeah," she answered and she swirled the liquid in a beaker, "I heard about that party last year. It's no big deal." "Well, it is to me," I moaned. "I don't want to have to buy a skirt and I had kind of a bad experience in high school." She set the beaker down and turned to look at me. I proceeded to explain what happened with Diane and being a cheerleader for the day and how things fell completely apart after that. I explained I really didn't want that to happen to me again. "It sounds like you enjoyed yourself that day," she pointed out, "aside from the teasing, that is." "Well, yeah," I admitted. "I got real excited wearing her clothes. She had to give me something tight to wear to make sure I didn't have a bulge in my pants. That was embarrassing but I did have a good time with it." "Looks like you still find it exciting." She nodded toward my crotch where I had once again gotten excited thinking about it. I turned and leaned against the lab bench in an attempt to hide it. Pam snickered a little. "It's alright. I imagine wearing things like that for the first time when you are 17 would really be exciting." "Tell you what," she went on, "I'll give you a call tomorrow night. I want to check on a few things and I might be able to help you out." I reached for the beaker but my hands were shaking so bad that I had to let her do the rest of the work while I tried to keep the notes. * - * - * I grabbed the phone on the first ring. "Hello?" "Sitting right on top of the phone?" came Pam's voice. "It's a small room," I laughed. "Can you afford $20 for pizza?" she asked. "Sure," I told her and she gave me an address to meet her the next evening. * - * - * I found the apartment complex, double checked the apartment number and knocked on the door. I looked around a bit; it wasn't the nicest looking place, probably pretty cheap rent, but it was close to campus. I heard a lock turn in the door and it opened. I didn't recognize the girl on the other side. "Hi," she started, "are you Zach?" "Yes, Pam gave me this address," I semi-asked if I was in the right place. "Yeah, come on in," she stepped back opening the door to admit me. "She ought to be along in a few minutes. Have a seat." Inside the apartment was a lot nicer than the outside. The occupant kept it tidy and decorated it minimally. It was definitely a temporary residence for a student. I looked at the couch and chairs and after noticing an open book on the couch picked a chair to sit in figuring she had been on the couch. Still a bit anxious I sat on the edge of the chair. "By the way, my name is Stacy," she told me as tossed the book onto the floor. She was pretty like Pam, had the potential to look amazing if she put on make-up and such, but still looked good without it. "Pam told me about your upcoming party. Since she also stays in a dorm she asked if I would mind letting you guys use this place to find you something to wear." "Ah, sure, that's great," I stumbled through the words. "I've got money for pizza whenever we get ready for dinner." "Good deal, I'll call it in now," she went to the phone, "it'll probably take them at least an hour to get it here. Any requests?" "Well, I prefer no anchovies," I answered. "Works for me," she dialed the number and placed the order. Just as she put the phone down there was a knock on the door. Stacy trotted over and pulled it open. Pam came in carrying a garment bag. They greeted each other and hugged. "Oh, you got here before me," Pam spotted me. "Yeah, I hate to be late when someone is doing me a favor," I replied. "Pizza is ordered," Stacy announced, "so you have about 45 minutes to start your work if you like." "Are you going to be ok with this?" Pam asked me as she laid the bag on the couch and started unzipping it. "I really didn't think it would be a problem since you will be at a party with probably 60 other people, but we can work something out if you will be embarrassed trying these things on in front of us." "Well, like you said, there will be a lot of other people soon and it isn't like this is the first time I've done this," I stood up to take a look at what she had brought. "Not the first time?" Stacy asked. "Uh, no," I confessed. "Either Pam can tell you about it while I am changing or I can when the pizza gets here." "OK, I'm looking forward to hearing about this," Stacy crossed her legs lotus style on the end of the couch and peered into the bag as Pam opened it. "Wow, you brought quite a selection." "Only 6," Pam answered. "I wasn't sure what would work best or what he might like. Sorry Zach," she turned to me, "I didn't bring any skirts, just dresses." "That's ok," I could feel myself starting to react to the idea of wearing those dresses and tried to position myself so that it wasn't obvious. "OK, why don't you start with this one," Pam pulled a short dress out and handed it to me. "Bathroom is down the hall on the left, unless you just want to change here in the living room?" Stacy winked. The idea of that did not help my situation. I swallowed, "Bathroom will work. Thanks." I headed down the hall. I stripped down to my underwear and checked the dress out. It was white with a tank top style above a peplum at the waist. The skirt was very short, not even mid-thigh, and once I got it on realized it was very tight as well. I had the same problem as the cheerleader pants. "Well, come on out and let's see," Pam called from the other room. I left the bathroom but stopped short of entering the living room. "This is a little tight, I don't know if you really want to see this," I spoke just above a whisper. "Come on in here," Stacy responded, "I'm sure we can handle it." I stepped into the living room. "Wow, you actually have nice legs," Pam offered. "Yeah, but quite a problem too," Stacy pointed out. "What kind of underwear did you plan on giving him?" "Underwear?" Pam answered. "I didn't even think about that, all I brought was the dresses." "Oh good grief," Stacy shook her head. "You're lucky Zach. I've decided I like you. After what you did for your idiot girlfriend in high school I think I can help you out today as well. Hold on a second." Stacy left the room and I went to look at what my next dress would be. I wasn't sure it would be much better. It was longer but looked to be as tight. One thing about the cheerleader skirt is that it was loose enough that it didn't look like there was a small animal hiding under it. When Pam returned she handed me a bra and a pair of panties. The bra had a smooth cup that looked like it would be really stiff, though it felt soft. The panty looked like a bikini bottom, two strands of fabric connected the front and back at the hip. Both the bra and panty were a lime green. "Let's see how those fit you and if they work but need a different color we can do that too," Pam flopped back onto the couch. "Thanks," my hands were shaking again. "I appreciate it." "Just don't get anything on them, OK?" she laughed. I snickered nervously and took the next dress back to the bathroom with me. I peeled out of all the clothes and pulled the panty on first. It felt smooth against my skin and though I was completely covered I could see that light was shining through the fine meshed fabric where my dick was tenting it away from my skin. They were tight enough to reduce the bulge even though they didn't eliminate it completely. A lot like the thong Diane had given me but they felt different maybe because they covered my butt rather than diving in between my cheeks. I struggled getting the bra on because this one fastened in the back. After failing at reaching behind myself, I finally hooked it in front and spun it around pulling the straps up over my shoulders. Once settled I pulled the dress over my head. This one was knee length and I liked that a bit better. It was one thing to wear a short cheerleader skirt with pants that you knew people would eventually see, but another to have to worry about giving someone a view that wasn't planned. The top of this dress was like a shirt with sleeves that came to my elbows. It looked like it wrapped around me like a robe and had a matching belt that tied around my waist, the skirt had a flap though it was sewn so that it didn't really open. I liked this dress better. It was also just loose enough at my hips that my problem wasn't as evident. I walked into the living room with more confidence in this one. "Very nice!" Stacy commented, "but it needs something a little more." She went to the kitchen and returned with some paper towels which she wadded up and reached into the front of my dress stuffing the bra with them. "We'll find something better once we find the right dress," Stacy told me. "Looks like the underwear works for you too." Pam just looked me over nodding. She reached into the bag for dress number three. It was red and black sleeveless. I returned to the bathroom. This dress was again well above my knee but not as short as the first dress. I had some trouble getting it on at first because there was a lining in it that I kept getting my hand in between it and the skirt and there was no way out. I finally got it on and decided I liked this one best so far. It was simple, the collar scooped just below my neck, the skirt was full and it actually had pockets! I went back for the next appraisal. Stacy shook her head, "It really is a crime how good you look in these dresses. With a little make-up I bet we could pass you off as one of the sorority girls." "I know," Pam joined in. "I'm going to feel subconscious about how I look next time I wear one of these." "Oh, please," I scoffed. "I know you are just trying to make me feel good. There is no way I can look anywhere close to as good as you in these." "Well, no," Stacy agreed, "but you do look good." "Next one," Pam handed me another dress and I carted it back to the bathroom. This time it had a zipper in the back. I got into it and found it was a black dress, much the same as the previous dress, it was sleeveless with a v neck, and almost as short as dress number one. The difference here was that it had a high waist where a sheer blue skirt started and layered over the top of the black dress. The front of the blue skirt came to just above my knee while the back reached almost to the floor. I went back to the living room imagining how the blue skirt might be flowing behind me as I walked. When I got to the living room Pam saw I needed zipper help and sealed me into the dress. As I turned for their evaluation there was a knock at the door. "Pizza is here," Stacy jumped up to get the door. I scampered back to the bathroom. "Zach," Stacy called, "we need the money for the pizza!" I was stuck, I couldn't get out of the dress. I pulled the money from my wallet and walked back to give Stacy the money acting as if everything was as it should be. Fortunately I didn't recognize the pizza delivery guy, probably a local high school kid. He snickered as I turned away. "There goes your tip," Stacy told him as she took the pizza and closed the door. "OK," Pam said, "Let's finish this up before we eat. I don't want to take any chances of getting pizza sauce on these dresses. I have two more left for you to try if you want. They really aren't appropriate for this party but while I was picking dresses out of the closet I thought what the heck. If you were game for going this far, maybe you would like to try them. They are on the more formal side." "Really," Stacy added, "you realize a lot of guys would have just looked at the dresses in the bag, tried on one that they thought would work to be sure it fit. Probably wouldn't have given us a chance to see him in it. I think you are really getting into this. But that is ok, because Pam and I are too! She wouldn't have brought the extra dresses otherwise. Please, keep going." I would have done it without a second thought but now that they had said all that I started thinking about it and whether I should do any more. That sat patiently waiting for my decision. "Could one of you please unzip me?" I turned my back on them. "Does the next dress have a zipper too?" Pam jumped up to unzip the dress and Stacy clapped her hands. "Look," Stacy said, "why don't you just change here instead of running back to the bathroom each time. Maybe we can speed it up a little so the pizza doesn't get cold." "That's true," Pam added, "besides, you will still have on bra and panties and it isn't like you've never been naked with a girl before." The top of the dress sagged as the zipper released it. I held it in place as I turned to face them. I couldn't say anything. I didn't know what to say. "You haven't been with a girl, have you?" Stacy asked. I nodded my head slightly, even more embarrassed than when they saw my erection through the first dress. "Hey," Pam placed her hand on my bare arm. "That's ok. I think it is sweet that you haven't done anything yet." "Out of curiosity, what have you done?" Stacy asked. "I've kissed," I said. "No touchy, feely? Under the sweater over the bra? Maybe over the sweater?" Stacy pried further. "Stacy!" Pam scolded her, "Let him be." I just shook my head no, I hadn't done any of that. "Wow," Stacy leaned back on the couch, "a real live virgin." "It's ok," Pam assured me. "Absolutely nothing wrong with that. Some of us don't jump into bed on a whim." "I'm sorry," Stacy added back. "I just never came across a guy that was willing to wait without getting something. I'm not making fun of you, I really respect you. And if you want to change in the bathroom that is perfectly fine." I looked at Stacy for a moment and then at Pam. They were both nodding slightly. I knew they meant it and this was a special moment, at least to me. My trust had been betrayed by Diane but I felt I needed to extend it again or I wouldn't be able to trust anyone ever. I slowly lowered my arms and let the dress fall down off my body. I stepped out of it and handed it to Pam. "Could you put this back on the hanger for me?" She smiled and took the dress, then laid it over the back of the couch. "You left the hanger in the bathroom, we'll get it later." I reached in and pulled the next dress from the bag. Like the previous dress it had two layers: the dress itself was a silver sequin strapless sheath covered by a sheer black striped sleeveless dress. The length was once again just above knee length. Pam zipped the back of it which was cut into a deep v that went well below my shoulders. It felt strange to not have anything on my back. "You couldn't wear that bra with that dress," Stacy observed. "Well, this dress is too formal for the party he is going to," Pam added. "This crosses the line from trying hard to what's he up to? I do like it on him though. Once again, you look great." "Thanks," I looked around to see if there was a mirror where I could get a view, "but you know, I would really like to see you in one of these dresses. I think you would look phenomenal." "Well, let's get you into the last dress so we can eat," Pam stated as she unzipped me. I stepped out of the dress and handed it to her, not even thinking about standing there in my lime green bra and panties any more. Stacy handed me the last dress. The fabric shimmered shades of blue and teal along the pleated floor length skirt. I found the zipper and opened it and stepped carefully into it. Stacy helped make sure I didn't stand on the skirt as I pulled the straps up onto my shoulders. The top was black felt not much more than the bra I wore. Two straps, one over the shoulder and one that draped down onto my arm met where two broaches seemed to hold them together. The back was cut as deep as the previous dress. The skirt began just below my chest and fanned in pleats down to the floor, it actually dragged a little bit. I ran my hands over the fabric as I moved about the room being careful not to trip. I loved the feel of the material as it slid around my legs as I walked. Pam smiled at me. "I wear a high heel with it of course. Since we are about the same height it drags a bit for you. Once again, it is too formal for this party. They will expect all the guys to be showing up in short skirts mainly. But keep it on for a while." I looked at her wondering what she meant. She reached up and pulled her shirt off then unbuttoned her jeans and pushed them to the floor. She was in a black bra in the same style I was wearing, but her panties were low hip hugger style with a broad pink lace band at the top. She reached for the black dress I had just taken off and I saw that her panties were not quite a thong but exposed the bottom part of her cheeks. She slipped the dress over her head and deftly zipped it. "OK," Stacy said as Pam adjusted the dress. "Zach looked really good but you do look better." "I'll say," I added. "Thanks," Pam blushed a bit. "So, be as careful as you can please, but let's eat." "Oh, hold on a minute," Stacy called, "I'll be right back. Go ahead and start dishing out the pizza, Pam you know where everything is. And there is a bottle of wine in there too. Let's open it. Don't expect much though, it's pretty cheap." Pam and I went to kitchen and started getting dinner set out. I couldn't take my eyes off her she looked so good in that dress. I tried to imagine what she would look like if she had done the whole make-up and hair routine. She might actually give Diane a run for her money. We took the plates and glasses to the little dining table and as we sat Stacy returned wearing a strapless evening gown. I sheer black skirt over the black dress underneath. "I'm not going to sit here looking like a slob while you to are looking all glitzy," Stacy told us and handed us large napkins. We managed to get through dinner without any accidents and discussed my choices. I voiced my regret in not being able to wear the long dress I had on but they assured me it would not be good for that party. So I decided on the fourth dress, the one that had the sheer hi-low skirt. They felt that would be a good choice for me. Stacy said she would lend me a black bra and panty to wear with it. "What about shoes?" Stacy asked. "I imagine I'll have to wear something of my own. I have a pair of sandals I could wear because I certainly can't wear socks with it," I shrugged. "Maybe," Stacy looked pensive. Then she disappeared from the room again, skirts flowing out behind her as she went. "See if you can get your foot in these?" she handed me a pair of sandals, black with about a two inch high heel. I sat on the couch and pulled the long skirt up so that I could get to my feet. I slid my foot into one and it was tight. I worked it a bit until my toes hung over the front by a fraction of an inch. I got the strap around my ankle and buckled it, my heel was off the back by a bit as well. "I think you should put the other dress on again so we can see," Pam suggested. I nodded and stood up. Pam unzipped me and helped me step out of the dress. Stacy handed me the dress I would wear to the party and I got it on, difficult wearing just one high heeled shoe. Once I got it on I sat on the couch again to try and put the other shoe on. Pam squatted down and put the shoe on for me. While she worked to get it on and buckled I noticed I could see up her dress since she had pulled it up out of her way. Even though I had seen her standing there in her underwear just a short time ago, I couldn't help but stare at her panties for a moment. When I realized I looked at her to see if she had caught me staring when I saw she was looking up my dress. Our eyes met and she looked away embarrassed at having been caught. "You two are just too cute," Stacy laughed. "I'll bet it won't be too long before something is going on with you." Neither of us said anything. We tidied up the dinner dishes and glasses. I got my things from the bathroom and helped Pam get the dresses back onto the hangers. She slipped back out of the dress she had put on and I hung it up and stowed it in the bag while she finished dressing. I then took the shoes off and the dress. Pam put the dress back in the bag while I removed the bra and paper towel breasts. I dropped it on the couch and then suddenly stopped as I realized I was about to remove my panties with them both standing there. "Do you really think it matters?" Stacy asked. "Those panties aren't hiding much of anything," Pam agreed. "I think if you had a mole on it I would already know." "I didn't realize you were looking that close," I teased. "Tell me you didn't try and see through her panties when she was changing clothes," Stacy teased back. "Easy for you to say who changed clothes in the other room," I came back. "Oh, I have a feeling we'll do this again sometime and we'll all be changing in front of each other," Stacy finished. I dropped the panties to the floor, my cock standing at attention as I grabbed my shorts and pulled them quickly on. I grabbed the rest of my clothes and finished getting dressed. "Why do you choose to wear jeans when you can wear skirts?" I asked them. "Because it is easier to lounge around in jeans," Stacy answered. She had her knees pulled up but had wrapped her arms around under her dress pulling it tight around her legs. We agreed to meet again on Saturday around 6:00. My party started at 7:30 and they felt that would give them enough time to have me ready. * - * - * Saturday rolled around and I went over to Stacy's apartment. When I got there Pam was already there, the dress I was to wear hung on a doorframe. "Are you ready for this?" I asked them. "Us?" Pam asked. "What about you? You're the one who has to go through with it." "I know, but you two are going to try and make me presentable without making me look like a drag queen in training." "Go get dressed," Stacy commanded. I took the dress and noticed a bra and panty were looped around the hanger and went to the bathroom. This time the bra and panty were black, same style as before. I got them on and slipped the dress on. I couldn't zip it so I went back to the living room with the back open. "I did your breasts the same way you told me that girl's mom did them," Stacy explained. "Drop the front of your dress so I can load you up." I did as I was told and she created my breasts for me. Once she felt they were correct she helped me pull the dress back up and zipped it up. I was led to the couch where Pam and Stacy went to work on my face. They explained that while they would normally do a more dramatic make- up job on themselves for a party like this, for me they just wanted to soften things a bit so I looked good in the dress, not too male. While the frat boys might not think much of it the sorority girls would likely love it and their opinion for this party would carry a lot of weight with the guys. I didn't understand how understated make-up would be better but when they finished I was once again shocked at what I saw in the mirror. The last time I had garish eye shadow and bright red lipstick as the cheerleader. This time my eyes were shades of tans with a touch of blue to match the dress just above the lashes. My lips were a pale red, not quite pink. And the rest of my face had been evened out. "Well?" Pam asked. "I think you've done an amazing job," I confirmed. "I'm sorry, but this is amazing. I think it is the best thing I have done yet. Thank you." "What are you sorry for?" Stacy asked. "Because," I explained, "now that you've seen me as a girl, you'll probably get grief over it and hope I go away." I felt a tear start to well up and willed it back so as to not mess up my make-up. "Just because that happened before doesn't mean it will happen again," Pam assured me. "Yeah, that girl was an idiot choosing her snobby friends over you," Stacy added. "You can say that because you have only met just me," I rationalized. "No," Stacy stepped closer and stared me in the eye. "I can say that because you went out on a limb for her and when the going got tough she abandoned you for a bunch of judgmental fools." "We've only been away from high school a year longer than you have," Pam went on. "We remember how the cliques work. You are a far better person than anyone has given you credit for being." Stacy reached up with a tissue and snagged the tear before it spilled down my cheek. "Now, enough of that," she whispered. "Go dazzle them with our handiwork." I laughed and gave them each a hug and a kiss. Stacy handed me a clutch explaining it contained things I would need. I walked across campus to the party. It wasn't that far but because my shoes didn't fit right my feet were already aching by the time I arrived. Several people were already there. I saw two of the guys standing there in black skirts but otherwise regular guy clothes. One other guy did wear a dress, but it looked like a joke on him due to his hairy legs, no chest. I was beginning to think I had made another mistake. I walked in and found some punch to drink, then I took a seat carefully arranging my dress as I sat. I was away from everyone so I could watch the room. It quickly filled up over the next few minutes. Two of the sorority girls approached me. I swallowed preparing myself for what was to come. They were both wearing dresses comparable to mine except they wore a sash that identified them as pledges for their sorority. I had my pledge pin attached just above my left breast. "No, see, it is one of the pledges," I heard one say. "Wow, that's amazing," the other responded. I stood up and smoothed my dress to be sure it wasn't sticking to me anywhere. "Hi," the first started. "I'm Gena and this is Vy." "I'm Zach," I extended my hand. They each shook it gently. "I can't believe you dressed up this much for this party," Vy stated. "I had help from a couple friends," I explained. "They thought I should do more than just throw on a skirt and walk in the door. Truth is, I agreed with them." "Oh, we agree too," Gena went on. "I mean look at that guy over there. I followed where she pointed and one of the guys in a black skirt was now sitting on a folding chair, his knees pointing in different directions, and even from across the room the boxers he wore under the skirt were visible. "I mean, that just looks gross," Gena added. I scanned the room again and saw most of the guys had done as little as needed to meet the requirements for the party. Another girl was coming over. "You girls need to be mixing in with the boys." Then when she got close enough, "Oh! I'm sorry, I didn't realize." "Sister Christi, this is Pledge Zach," Gena introduced me. "Sister Christi," I offered a little bow of my head and my hand. She shook it briefly and looked me over. "You have certainly taken this to the next level, Pledge Zach." "Yes, Sister. I believed you ladies deserved my best effort." "Are you in drama?" she asked me. "No, Sister, I just have very talented friends." "Very good. Thank you for putting in the effort." She turned to the other girls. "Pledges, I still think it is time you mingled with some others. Pledge Zach, I leave it to your brothers to dictate where your time is best spent." They left me and I decided my feet had recovered enough that I could start mingling. After wandering around I ran into a couple of the senior brothers. "What the hell, Pledge Zach," the first bellowed. "Are you pledging us or the sorority?" "Us, Brother Matt," I responded standing straighter. "Shit, I bet you are even wearing panties under that dress. You were just required to wear a skirt not transform." The other brother was laughing at me when someone stepped up behind them and whispered something I didn't catch. The looks on their faces changed to ones of bewilderment. "Really?" I heard Brother Matt respond. "OK." He turned back to me, "Well, it looks like you've really impressed the sorority with your effort. They have chosen you as top pledge for this evening. With that endorsement you are all but accepted into the frat. We'll be taking a final vote tomorrow, but let me just be the first to say welcome, Brother Zach." "Brother Zach," the other shook my hand and they disappeared. I stood there stunned for several seconds. Then I gathered my wits and visited with everyone. The other frat pledges still teased me about my dress but all the sorority girls seemed to make it a point to spend time with me. A few of the brighter frat pledges started to realize that the girls really liked what I had done. The party broke up and I walked back to Stacy's apartment. When I got there she and Pam were watching a movie on TV. I collapsed into the chair unconsciously spreading my ankles so my knees would stay together. I told them all about the party and the news that I was expecting the next day. I thanked them over and over for what they had done for me. "So, I guess the big question now is that since you are going to be a big frat boy, are you still going to want to hang out with us?" Stacy suddenly asked. At first I was shocked into not speaking. The idea that I wouldn't want to hang out with them was not even something I considered. Would the frat try and dictate that? "I would quit the frat if they try and make me stop hanging out with you, either of you," I swore. "I bet you would," Pam grinned. "We have been talking," Stacy went on. "My lease here is up at the end of the semester. We could get a larger apartment, two or three bedroom, and split the costs. We would be able to afford a nicer place together. What do you think?" "Me living with the two of you?" I had to ask, I couldn't believe they were suggesting it. "Yes, all three of us," Pam assured me. "You've seen Three's Company haven't you?" I remembered the show she was talking about. It ran on TV Land or Nick at Nite or one of those stations that ran old shows. One guy living with two girls but nothing ever went on between him and the girls. I nodded. "Well, it will be something like that." Pam confirmed. "Not exactly like that," Stacy came back. "Even though you probably won't have any more parties where you get to wear a dress, we are hoping you will still want to have a party with us. We really enjoyed our formal pizza party the other night." I didn't miss the fact that she said "get to wear a dress" instead of "have to wear a dress". I knew I had lost all pretense of not really wanting to wear a dress during the trying on session just a couple days before even though it was only the second time I had ever worn any kind of girl's clothes. "I would love it," I answered. "Oh, and you might be ok to get involved with one of the roommates," Pam added blushing a little. "Fine," Stacy added, "I bet you are ready to get out of that dress." She stood up. "I guess so," I reached down to unbuckle the shoe and looked around to see where my clothes were. "I'll be right back," Stacy left the room. I got the shoes off and stood up going over to Pam to unzip my dress. She unzipped it and ran her hand across the bare skin of my back. A chill ran up my spine. "OK," Stacy called as she came back into the room. She had changed into a pink baby doll nightie, her matching pink panties easily visible beneath the edge. "We have another movie we can watch together so let's get really comfortable." She tossed me a black baby doll and a green one to Pam. "Sorry, Pam, didn't know what color panties you were wearing so you get the green one. I have orange and red if that is better." Pam laughed. "Green will be just fine." I took my dress and bra off and pulled the nightie over my head. I was surprised to see Pam strip down to her panties, her nipples standing stiff as she slipped the nightie on. I saw Stacy shake her head as she caught me staring at Pam. I looked over at Stacy and could easily see the shape of her lips outlined within her panties. I knew that they could just as easily see what was stiff in my panties as well. I just smiled and moved to sit between them on the couch. Pam started the movie. * - * - * We got all moved in together the next semester. We found a great three bedroom place that cost just a little more than double what Pam was spending on the old place. We decided that three bedrooms would be best, and if circumstances changed we would be able to convert the extra bedroom into an office. The first weekend we were in the new place we had a real formal dinner together. Better wine, steaks, and all of us in floor-length gowns. This time Stacy let me borrow one of hers. They went all out fixing their hair and doing their make-up, as well as doing my make-up. This time they did me up for a formal night with very dramatic eyes and lips. We had a wonderful time together. Pam and I started dating right after we moved in together, which sounds strange when you think about it. But we were just so perfect together. Stacy said she never had a doubt about us and looking back I think she may have pushed us very gently to get things going. I found a part time job off campus that paid a lot better and still left time for my studies. I used some of the extra money on some clothes for myself. We enjoyed spending our free nights (of which there weren't many) sitting in our nightgowns watching movies. I also started collecting my own panties, bras and things. I knew I would need to be borrowing their dresses for some time to come but I thought it best to have my own foundations. Stacy said she thought it was exciting sometimes thinking about me wearing her things, so I assured her I would still borrow things on occasion. I think she purposely started buying some sexier things like garters and stocking just so I would want to try them. I think she also knew it got Pam really turned on too. One other thing they did was to buy me a pair of breast forms to wear. They said they were tired of having to buy flour and paper towels all the time and this would be cheaper. After about four months of living together and dating, we had planned on another formal dinner for Saturday night. I went to my room and found that someone had laid out an outfit for me to wear for dinner on my bed. I never questioned who did it, if one of the ladies wanted me to wear something special I would happily accommodate their desire. In this case it was a strapless black dress. The skirt was short and had many layers so that it spread out around my legs. A strapless black bra and a see-though black panty. Also a black lace garter with silk seamed stocking. My black high heeled shoes were set out beside the bed under the dress. I quickly changed clothes and went to do my make-up. By now I had gotten pretty good at doing my own work so the girls were free to get themselves ready without having to worry about making time for me. I finished touching up my lipstick and went out to the living room. Pam emerged from her room a moment later looking like a model. She was in a black column dress that had a slit up her left leg. When she walked toward me her leg flashed and I saw she was wearing stockings as well but the garters were wider. We met in the middle of the room with a hug and a kiss and waited for Stacy to emerge. After a couple minutes Stacy did enter the room, dressed in a gray sweatshirt and jeans. "What is going on?" I asked. "Something came up, but don't worry, you two can have a good time without me," Stacy explained. "I'll probably be back around midnight." "But it is tradition for us to do these together," Pam pleaded. "It's ok. You both look wonderful," Stacy hugged and kissed us both. "Enjoy your dinner. Have fun and I'll either see you later tonight or in the morning." She disappeared out the door. Pam and I looked at each other for a moment and then went about making dinner. Once we got seated we toasted to our friendship as was our custom at these dinners and to Stacy though she wasn't with us this evening. "So, when did you get that dress?" I asked her. "I didn't," she answered, "I thought maybe you bought it for me. All this stuff is new and was waiting on the bed when I got home." I sat back in my chair. "Yours too," she went on. I nodded. I also started getting very excited. I knew that as sexy as the dress she wore was, the underwear would be even sexier, probably more than what I was wearing. I could see she had reached the same conclusion. Tracy had set us up apparently tired of the slow pace at which we were taking our relationship. We finished our dinner and while cleaning up I approached Pam from behind and reached around her slipping my fingers inside the slit in her dress. My fingers traced up the silky stocking and onto her bare skin. She leaned back against me and I knew she could feel how turned on I was even through the multiple layers of fabric in my dress. I kissed her neck and let my fingers wander to her panty. The material felt the same as what I was wearing but I felt ridges like stripes that ran vertically on them. Pam suddenly spun in my arms and wrapped an arm around my neck pulling me into a kiss. Her turn did not remove my hand from inside her dress but instead I had it on her ass, her dress folded back exposing her, my dress now rubbing against her legs. Her other hand sought the hem of my dress and began searching through the layers until she reached my panties and the hardness within. She moved them and wrapped her fingers around me, the first time anyone had ever touched me. I gasped. "Wait," I gasped again. "You don't want to?" she panted. "Oh, yes, I do, really I do, but I'm afraid I will cum too fast. I don't want to get anything on my dress or yours. Let's get them off and go to my room or yours. I hope I can be good for you." "Oh, don't worry," she pulled my panties back into place and lowered my dress. She backed away putting her dress back into place as well but not before I saw her panties did indeed have stripes, black silk alternating with see-through black mesh. "I think we will do just fine, we have all night." We took care of one more thing before heading for Pam's bedroom. I watched her strip off her dress, bra and finally her panties. Then she helped me take off mine until we were both left in the garter and stockings. I did cum quickly the first time too soon after we got started but youth has its advantages and I was ready to pleasure her within a few minutes. Pam was amazing teacher and I was an eager student. She instructed me on how best to pleasure her. We both came the second time together and the third time as well. Somewhere during the course of our exertions we heard the front door open and close. We knew she found the sign we left for her: "Thank you, Stacy! You are the best, we owe you one!" * - * - * Unfortunately time passes and Stacy and Pam both graduated. I was still a year behind. Stacy took a job in another town and had to move. Pam decided to wait a year before finding a job and continued to work the part time job she had been holding. We managed to hold onto the place while I finished up but it wasn't the same without Stacy there. In truth I couldn't wait to graduate so we could move on. At last my graduation day finally rolled around. Stacy came back so we could all celebrate together. We went out on the town one night and had one of our special formal dinners together the next night. The following morning I was searching for a job for both me and Pam where we could both go together when I found something that was perfect. Not only would we be able to both find jobs in the same area but we would be less than 25 miles from where Stacy lived. Six weeks later we got confirmations that we had the jobs. We went house hunting looking for an area between us and Stacy; she came along and looked as well. Our luck held as we found a nice little house that had an in-laws quart