Experimenting in College- Part 1
If you had told me a week ago that I would be dating a guy and working as a waitress I would have called you crazy, but a week later here I am and doing exactly that. You see I'm a straight guy named Chris who has a girlfriend and has zero interest in men or dressing as a woman, but to get into the most prestigious fraternity on campus I had to play along and live as Crystal for a week. Now you're probably wondering why a fraternity would have its potential members go through something like this and that's because a few years back some of the frats were shut down because of some sexual harassment issues with multiple sororities. Although this was not one of the fraternities responsible, it was decided that new members pledging any frat were required to spend a week as females as part of a sensitivity exercise rather than shut down the entire Greek program. So for the past week my best friend, Adrian, and I have been living as Crystal and Adrianna. This has included getting temporary campus IDs with our female names and photos, attending classes as girls, going to campus events and parties, participating in fundraisers, and getting jobs. Now while not every guy pledging is passable as a girl, Adrian and I actually make very convincing and very attractive females. So now that you're caught up, let me tell you how our week has gone so far.
The weekend before our pledge week began, we were all set up with appointments to get our hair, nails, and makeup done; our body hair waxed; our prosthetics attached; our wardrobes for the week purchased; our ID cards made; find jobs; and get instruction on living as a girl and finding our own unique style and female identity. The goal wasn't just to spend a week dressed as girls, they wanted us to really experience what life is like for a woman. While some guys needed wigs, Adrian and I both had long hair so they trimmed our hair into more feminine styles for the week while maintaining the length. We were also each given small doses of estrogen that we were to take each day. The effects weren't permanent, but were carefully designed to help put us in a more feminine mindset for that week. Among other things they were designed to stimulate our sexuality.
Although we both thought the ritual was stupid, Adrian and I both really wanted to get in so we played along and worked on creating Crystal and Adrianna's personalities. Adrian decided it would be funny to make Adrianna super girly and obsessed with taking selfies, looking hot, and showing off her body while I made Crystal feminine and artsy, but slightly more reserved. We both created Instagrams, Facebooks, Snapchats, and Google/Gmail accounts for the week and took a selfie together for Adrianna's first post which she captioned "Me and my bestie." I could tell he was starting to have fun and was getting into character, but I was still having trouble getting into the female role. As you can expect, Adrianna had already posted a ton of social media posts by the time the day was over while the only things I had posted were profile pictures and a repost of the selfie I had taken with Adrianna.
On Sunday night, all of the "girls" dressed up in white dresses and were presented at a party with all of the fraternity members. Although I was planning to wear a floor length gown, Adrianna convinced me to wear a much shorter dress that showed off my long legs. As much as I hated to admit it at the time, I looked hot in that dress. Even my girlfriend thought I made a better looking girl than she did after she saw the photos Adrianna posted. That night when we were presented before the party, I could sense every guy in the room checking us, and some of the other convincing girls out. Although I hated how good I looked at the time, I have to admit now that it feels kind of nice having that kind of power over people, even if it is for sexual reasons. It's rare that guys are able to use their sexuality to get someone to do what they want. At least for me it is, I'm not the most masculine looking guy as you can probably guess.
After we were all presented, the party began and each of us were observed to make sure we stayed in character for the night. although some of us slipped up now and then, some of the pledges thought the whole thing was gay or stupid and either left or were forced to leave. By the end of the party, only twenty of us remained. Throughout the night each of us practiced speaking in our best female voices, danced with each other and some of the frat members, and experienced what it was like to meet guys. By the end of the night Adrianna had made out with one guy, Alex, for most of the party and disappeared with him multiple times throughout the night. Although Adrian was straight, he had never had much luck with girls and I could tell that he wasn't so much interested in guys, but liked having someone who wanted him, even if it was a guy. I have to admit, he slipped into the female role rather easily and I was getting turned on watching the guy stroke her smooth thighs as he kissed her lips, neck, and shoulders as she giggled as he would pause to whisper in her ear presumably telling her how beautiful she is.
As much as it pains me to admit it, I was kind of jealous of how quickly she was able to slip into her role. Throughout the night, guys would get me drinks, ask me to dance, and strike up conversations with me, but although I played along so as not to get kicked out, I was still feeling pretty uncomfortable having all these guys treating me like a girl. That all changed, however, when I met Trevor. Unlike the other guys, he tried to ease my awkwardness at the situation by offering tips and sharing his experiences from when he was a pledge. Although he was much taller and muscular than me, he had plenty of helpful pointers.
"You're actually lucky you can pass as a girl, he said as we sat on the patio drinking our drinks and smoking a bowl, "do you know how hard it was finding clothes and shoes that fit me. There aren't a lot of big and tall stores for women."
"I guess that's true," I said with a small laugh, "I guess it's still just feeling kind of strange for me."
"Don't worry," he replied with a smile, "I'll be here to help you out and before you know it the week will be over and you'll be back to your old self."
"Thanks," I said as I pulled his coat closer around me that he had let me wear because it was cold outside and the dressing I was wearing left very little covered up.
I ended up spending the rest of the night with him mostly just talking, but also dancing a few dances together. Although I had only met him briefly during rush week, I felt safe with him and he didn't try to make any moves on me like a lot of the other guys had done with me earlier and with some of the other pledges. By the end of the night I was no longer feeling so out of place in the situation and was starting to feel more comfortable as Crystal. We kissed a little, though it was just a few pecks and nothing overtly sexual, and at the end of the night when I discovered that Adrianna had disappeared with Alex, he held my hand as he walked me back to my dorm. We had already exchanged numbers and added each other on social media earlier in the night and when we reached my door we made plans to have lunch together the next day between classes. As we stood there a part of me was not ready for him to go, but I was afraid I might end up doing something I was not ready for, so I kissed him one more time and went inside closing the door behind me. The kiss lasted slightly longer than the ones we shared at the party, but at the time I was still not fully comfortable kissing a guy, no matter how good a guy he seemed. I removed my makeup and changed into some of my new sleepwear and lay in bed looking at some of the posts from the party before falling asleep. Adrianna was still not back yet, but had texted me saying she would catch me up in the morning.
The next morning I woke up and got myself ready for my first full day as a girl. I decided to wear something simple and not too revealing as I wasn't sure how other students would respond to my feminine appearance and did not want to draw any unnecessary attention to myself. After a quick shower, I put on a pair of jeans, a t-shirt with the university logo, a light jacket, and a pair of Vans, did my makeup, put my hair in a ponytail, gathered my things, and left for class. I woke up really early despite being slightly hungover from the night before because the showers were co-Ed and I was scared of guys coming in and seeing me in just my towel. Most of the people on my floor were not pledging the frat and would probably would mistake me for a real girl.
As I rode down in the elevator, the elevator opened and a guy walked in from another floor. He smiled at me and started to make small talk. It turned out we were both headed to the same class and had the same major. Even though I wasn't showing any skin, I could tell he was checking out my ass and tits. Although we were required to stay in character for the week, we were allowed to tell people of our true gender if we felt necessary.
"Oh, I'm Greg by the way," he said reaching out his hand.
"Crystal," I replied shaking his hand, "but I should tell you I'm really a guy. I'm pledging a frat and have to spend the week as a girl."
"Oh wow," he said not appearing angry, "I would have never guessed. I hope this doesn't make you uncomfortable, but even knowing you're a guy, I still find you really attractive."
"Thanks," I said blushing slightly, "I've been getting that a lot. I'm actually straight, but I am starting to kind of like the compliments. "
"Well," he continued, "you'd better get used to it because you're gonna get a lot of them this week. I hope this isn't too forward, but have you ever been with a guy before."
"Not before this whole experience, but last night this one guy and I kissed a little," I admitted reluctantly.
"Did you like it?" He asked curiously.
"I don't know," I replied honestly, "I know I haven't suddenly turned gay, but it wasn't too bad. It was a lot different than kissing my girlfriend, but it wasn't as weird as I'd expected it to be."
When the elevator opened we continued walking together to class and he seemed genuinely interested in hearing about my experiences as a girl so far. He admitted that although he had never thought about dressing as a girl, he had sometimes wondered what life would be like as a girl. I have to admit that before this whole experience the thought had crossed my mind once or twice. I assume everyone has wondered what it would be like if they had been born the opposite gender. Who would have ever guessed I would be experiencing it first hand.
While I had felt a comfort with with Trevor, we really didn't have that much in common. Greg, on the other hand, shared many of my interests and passions, including my reasons for picking psychology as my major. I was genuinely interested in what he had to say and although I wasn't thinking of him sexually, I found myself thinking we would probably have a lot of fun together if we were a couple. It's actually the same way I felt when I met my girlfriend, although with her there was also a physical attraction. That isn't to say Greg wasn't good looking. If I were attracted to guys I admit he would probably have caught my attention. As with Trevor, we exchanged information and added each other on social media, not only on my Crystal accounts, but on my Chris profiles as well. I was interested in getting to know him as a friend after this experience was all over.
My classes went by without any incident and Greg and I sat together in the two classes we had together. After class I had planned to meet up with Adrianna, but our schedules conflicted so I grabbed a coffee with Greg in the campus Starbucks. He invited me to have lunch with him later, but I told him I already had plans with Trevor.
"Wow, look at you," he teased, "only your first full day as a girl and you already have two guys. Look at you little miss popular. How about dinner then?"
"What can I say," I replied playfully as I was really enjoying spending time with him, "when you got it, flaunt it. And yes, I get off my new job at 9, but I would love to have dinner with you after."
"Great," he said, "I'll pick you up from your dorm so you can get ready. You probably want to change out of your uniform."
"Oh, you don't want to see me in my waitress uniform," I said somewhat flirtingly.
We both laughed as I looked down and realized we had been holding hands across the table for much of the time we were there. Although I started to feel somewhat self conscious about it I didn't pull my hand away. I was having a good time with him and was starting to feel more comfortable being out in public as a girl. When it was time for us to go our separate ways to our next classes, I stared longingly after him as he walked away after we shared a hug. Although I had already kissed a guy, I was feeling in a different mindset after smoking and drinking at the party and wasn't thinking as clearly when I was with Trevor. Although I still had a slight hangover, I was sober now and wasn't as comfortable going in for a kiss as I would have been had I met Greg at the party the night before. I could definitely feel the estrogen taking effect and was beginning to shape my thinking.
I went to my next class and found a seat between a few girls as I didn't want anyone I knew in the class to recognize me. The girls (Paige, Monica, and Emily) were very friendly and even after I told them I was a guy they continued to treat me like one of the girls. We continued talking before class started and for some reason I felt comfortable telling them about my experiences with Greg and Trevor and the "dates" I had with them later. They each offered some advice and warnings from their dating experience, and I admit it felt nice having some real girls to guide me through what it's like being a female. Although Trevor had offered me some pointers the night before, it was different getting a female perspective on things. As real girls, who were all quite attractive, they all had spent their lives experiencing what I would be going through throughout the week. They even agreed to pick me up after work later to help me get ready for my date with Greg. I had admitted to them that I thought the estrogen was starting to make me fall for him and they were all very supportive and understanding.
Throughout that morning Adrianna had been messaging me telling me all about her night with Alex. She was eager to tell me that although she felt weird at first, she really liked making out with him and that they had sex and she sucked his dick several times throughout the night before going back to his place and spending the night together. She shared details of how much bigger his cock was than hers and how she thinks she might be bisexual, but that it could have been because she had asked for a larger supply of estrogen to help her get through the week and was probably feeling its effects more strongly than I was. She went on and on about how hot he was and sent me numerous photos of him, the two of them making out, and even a couple videos of her giving him a blow job. I felt strange seeing this sudden transformation in someone who had been my best friend almost my entire life. Although Adrian had never had any desires to be a girl or any prior interest in guys, it seemed like the experience had awakened something in him. He was really loving his experience as a girl and sent me photos of the short shorts and tank top that Alex had picked out for her to wear to class that day. I could even see the naval piercing she had gotten that weekend because of how revealing her outfit was. We definitely had a lot to talk about in person later.
After my morning classes had ended, I went to the student union to meet up with Trevor for lunch. He was very sweet when I admitted that our kissing the night before was more a product of the weed and alcohol and I didn't want to give him the wrong impression about us. He was very understanding and figured that might have been the case. He asked me how my day had gone so far and I told him about Greg and my new friends. He seemed happy for me and how well I had been adjusting so far. Since last night the number of pledges had dropped down to fifteen. He also told me that a lot of guys, including himself, experienced dating during pledge week and that it generally resulted in the pledges having a better understanding and respect for girls when the week was over. In a few cases some pledges had realized they were possibly gay, bisexual, or transgender, but most returned to their normal lives after. As I listened I wondered if my date with Greg would awaken something in me as had happened to Adrianna or if I would be able to return to my regular life when the week was over.
I had also been telling my girlfriend, Becky, who I was in a long distance relationship with since she went to college out of state, about my experiences so far. Like everyone else she encouraged me to continue on with my week as a girl and that we would evaluate our relationship at the end of the week if the experience changed anything in me. It really felt good to have such an understanding girlfriend and made me wonder what kind of girlfriend I would be if I ended up having a boyfriend that week. The thought of being someone's girlfriend was much more possible at that point than when this experience had started.
After lunch Trevor walked with me to my next class. We didn't hold hands like we did the night before. Although he was a great guy and very good looking, we both realized there wasn't that strong a connection between us and that even while I was a girl we would be better just as friends. Having been friend zoned by girls before, I could now understand why it happens. Even though someone might be a really nice guy, it takes more to be in a relationship with someone. Now that I was thinking more like a girl, I had to admit I might have been down to hook up with him before the week was over if things with Greg didn't work out. Adrianna had gotten me curious what sex was like as a girl. I hadn't suddenly turned gay or anything, but I had begun to wonder what sex was like in the opposite role than I was used to. I admitted this reluctantly to Trevor and he told me he would be there if I decided to go through with it. If the way he had kissed me the night before was any indication, I imagined he would be a very gentle, but passionate lover. I began to get turned on as I thought about it and felt a strange urge to kiss him again. After all, it would be good practice if things went well with Greg that night. I wouldn't want to seem inexperienced if things escalated that night. Although we didn't kiss for it long, we made out this time as I let my lips part and our tongues briefly touched.
"You're a pretty good kisser," Trevor said with a smile as he pulled me in by the waist for another quick kiss.
"You're not so bad yourself," I replied as I felt our bodies press together as we kissed again.
I smiled at him as we separated and I reached for the door to my class. I could feel his erection pressing against me on that last kiss and knew I had to put a pause on this before I let things go too far. By this point the hormones had really begun to take their effect on me and i could tell he knew this too. He admitted the pills made him feel the same way when he was a pledge. I couldn't resist and gave him one more quick kiss before going into class. When I walked in I found Greg smiling at me and took a seat next to him. I could tell he and the rest of the class had seen the shilouette of Trevor and I making out through the fogged window on the door. To the rest of the class we seemed like any couple saying goodbye to each other. I didn't really know too many people in my classes yet as I mostly kept to myself, so nobody really knew me as Chris. The only ones who knew who I really was were Greg and Monica. I had told them both about the estrogen we had been given so I could tell they both seemed to understand the cause of my behavior.
"Should I be jealous?" Greg teased, "I hope our date is still on."
"Don't worry," I said softly, "just a little practice. You never know what might happen tonight."
By that point my flirting had become much more overt and I was feeling much more comfortable in my sexuality. I still wasn't sure if it was the estrogen or if I was really falling for Greg, but I assumed it was probably some combination of the two. After class I introduced him to Monica and after we talked a little, she politely requested we walk on on our own for a little girl talk. He was very understanding and I hugged him before Monica and I continued on our way.
"Wow, he's hot," she said, "Ive had a crush on him since the first day of class. I hope you don't mind setting us up when you go back to being a guy. "
"You better ask me when I'm Chris," I replied, "All this estrogen isn't leaving me thinking very straight. There must be something else in those tablets that they didn't tell us about because I've been having daydreams about a threesome with Greg and Trevor the entire class."
"Yeah, my ex had the same experience when he pledged last year, she said reassuringly, "once you stop taking them the effects go away in a day or two."
"I hope so," I went on, "I'm feeling so confused right now. I'm starting to check out every hot guy that's passed us."
"Welcome to my life," Monica teased.
Although I normally would have been checking Monica or any girl out when the semester started, in my current mindset I only saw her as a friend. I admit, even though I had a girlfriend, being in a long distance relationship was hard and we had both agreed to an open relationship. I had hooked up with a few girls since moving here and although I had never talked to her before today, I had had my eye on Monica since the beginning of the semester. Meeting her in my current state, however, made me think about the fact that I had never tried to make any female friends and had always looked at most of the girls I met in a sexual nature. I admit I felt kind of ashamed about this and admitted this to Monica. She was very understanding and we hugged after I apologized. Although my apology was to her, it was more of a symbolic apology to all women. I genuinely hoped she and I would remain friends when this was over.
We said our goodbyes as we reached the campus restaurant where I would be working for the next week. I went inside where I was given my uniform and name tag and went to the back to change. Although the uniform wasn't too revealing, it was definitely very feminine and form fitting. The skirt ended at the knee and the long sleeved blouse fit tightly against my thin waist and new breasts. The heels weren't too high, but by the end of the shift were definitely uncomfortable. I did have several guys flirt with me during my shift and even got a couple guys that gave me their numbers, but fortunately I was able to control my sexual urges as the effects of the pills had begun to wear off somewhat as my shift went on. By the time my shift had ended the effects had gone away almost completely and gave me a brief chance to think like myself again. I decided to cut the dosage down to one pill for that night and the rest of the week because two pills were much more than I felt I needed.
When my shift ended I took one of the pills and met up with the girls to get ready for my date with Greg. I decided it was best to take the pill then as I didn't want any awkward incidents undressing with the girls around. I thought about it for a moment and decided it wouldn't hurt to take one more. We went to my dorm, where I found a note that Adrianna left telling me she was out with Alex, and the girls went to work having me try on different outfits, including some of Adrianna's and some of their own that they had brought. At that moment I was feeling pretty glad that my body was more feminine than most guys and that I could fit into all these clothes and shoes. The girls felt I should wear something sexy, but not too revealing, especially after Greg texted me and told me he had made reservations at a nice Italian restaurant in the village off campus. We eventually decided on a simple black dress that ended a few inches above the knee and showed off a hint of cleavage. They went to work doing my long brown hair, which now had highlights from my weekend makeover, and makeup before spraying some perfume, added some jewelry, and having me slip into a pair of four inch heels. They handed me a clutch and had me turn to face the mirror to see my reflection.
I couldn't believe how gorgeous I looked. Although I had looked good at the party the night before, their talents far outshined my own. My hair had a slight wave and framed my perfectly made up face. I blinked my eyes admiring my long curled eyelashes and my full red lips. The dress hugged my body and accentuated my large breasts, flat stomach, thin waist, wide hips, and round ass, and the heels made my legs look perfectly long and shapely. I could feel the pill had already taken its effect and was eager for Greg to pick me up. The girls all seemed quite impressed with their work and offered my some quick advice for my date. I texted Greg telling him I was ready and he replied that he would be up in two minutes. When he arrived I opened the door where he stood looking like a total stud in his suit and he stared at me in disbelief.
"You look incredible," he said finally finding the ability to speak, "You girls did an amazing job with her."
"Thanks," Monica said trying to hide her awkwardness around him, "but she was easy to work with."
I could tell it was difficult for her to act casually around her crush, but she tried her best to put her feelings aside and support me potentially being his girl for the week. The girls left as he took me by the arm and we closed my door behind me. Any trepidation I had about dating a guy had disappeared and my only concern was that the date went well. As I realized earlier all of these feelings would likely go away at the end of the week, but for now I was a gorgeous eighteen year old girl out on a date with a hot nineteen year old guy. For now there was no Chris, only Crystal, and she was ready to take on the world. My thoughts had changed from the pills and I was thinking of myself as completely female. By this point I had begun posting almost as much on my social media accounts as Adrianna had been. I definitely would have a lot to report to the frat at check in that night.
My date with Greg was like a fairy tale. Being my first time going out on a date as a girl he wanted to make it extra special. Waiting at our table was a bouquet of roses and a singer sang us love songs throughout the night. I looked longingly into his eyes and could feel myself falling in love with him as he held my small delicate hand in his strong masculine hand across the table. I wanted to kiss him so bad, but held myself back as I wanted him to make the first move. He stood up and reached for my hand to dance as a violin player began to play for us. He held me close as I rested my head on his chest and melted into his strong embrace. I looked up into his eyes and smiled as he smiled back at me and soon we were locked in a passionate kiss. We made out for what seemed like an eternity as the world around us seemed to disappear. Even though he was only the second guy I had kissed, I felt like he was the greatest kisser in the world. The stubble on his strong draw grazed my smooth face as his lips found his way down my slender neck and bare shoulders. This must have been what Adrianna felt like kissing Alex.
By the time we left the restaurant and were walking hand in hand toward through the village toward the frat house I knew I wanted to spend the week as his girlfriend. Not only was he hot as hell, he was smart, funny, passionate, and what I imagined was the perfect man. When I returned to my life as Chris, I could only strive to be a fraction of the man he was. For that moment though I wished the week would never end and I could be his girl forever. I imagined us getting married and starting a family together. Of course I knew none of this was real, but for the moment it was fun to pretend. When we arrived at the frat house we kissed again and I didn't care who watched. I was his girl now and wanted the world to know. Reluctantly I broke the kiss and walked toward the frat house staring longingly back at my man.
Inside most of the pledges were assembled in the living room and after the rest of the girls had arrived, we were informed that there were now only twelve pledges left. Of the girls remaining, including Adrianna and myself, about half were quite passable as females. The rest were somewhat masculine looking, but had seemed to fall in well to their female roles so far. I looked over at Adrianna who was sitting in Alex's lap and she smiled back at me as he stroked her waist between the tank top and shorts she was wearing. You could make out the two piece swimsuit she was wearing underneath. As it turned out, Adrianna and I weren't the only ones who had found guys as each of the girls took turns sharing their first day experiences. One girl had hooked up with her roommate and another with one of her best friends. Some of the girls were still too nervous to experiment, but admitted they hoped to by the end of the week.
When the meeting was over Trevor asked me about my date and gave me my instructions for tomorrow's first pledge week activity. As was the custom, the first day was dedicated to each of the pledges getting comfortable its girls, but the rest of the week would have some frat challenge each day. My task for Tuesday was a charity bikini car wash, where I would be washing cars with Adrianna and two of the other girls. It just so happened that we were the four most attractive of the pledges and that Alex had been in charge of assigning the first tasks. It came as no surprise when that Adrianna wasn't the first pledge he had hooked up with. Despite this, he and the pledges were able to become friends and fraternity brothers after the week was over. In fact the pledges he had hooked up with last year and the year before were now two of his closest friends and he was always setting them up with the hottest girls on campus. As Adrianna later told me, that was part of why she hooked up with him. For now, however, that was the furthest thing from her mind as she just wanted him for his body and huge cock.
Before she disappeared with him again though, I pulled her aside for some girl talk with my bestie. Even though I had made new friends that day, I missed her and was anxious to tell her about my day and hear all about hers. She told me all about how they spent most of the day at the pool together after her classes and how great the sex was. She briefly touched on her classes and her job as a barista at the Starbucks, but most of what she told me was about Alex. I told her about my new friends and my experiences with Trevor and Greg. She seemed disappointed I haven't had sex or given either of them a blow job yet, but understood that I wasn't as ready for that as she was. She was excited we would get to spend time together at the car wash and was excited to meet my new boyfriend soon, but as I expected she was planning to stay at Alex's for the week and had already moved most of her new wardrobe to his place. Although I would miss her, it did mean I would have the dorm to myself for the week and would give me some privacy when I was finally ready to have sex. We hugged before she ran over to Alex and they left together.
I went outside where I found Greg had waited for me and smiled. He took my hand and walked me back to my dorm. When we got to my door I paused and considered inviting him in. As much as I wanted to have him spend the night, the pills were starting to lose their effect and I wanted to be in full girl mode for my first time. We shared a quick kiss as I wanted to kiss him one more time before the pills lost their effect. We said our good nights and I went inside closing the door behind me. I walked over and glanced at some of my new swimsuits wondering which one to wear and eager for my second day as Crystal as the pills wore off and my mind began to revert back to Chris.