Trans in College

Author's Note: Here is the first chapter of a new series set at a college. I didn't transition until after college, so I will be living a little vicariously through our protagonist in this one (:

Enjoy

Chapter 1 -- Welcome Week

"Hey! It's so nice to finally meet you," I said to Riley, the person who would be my roommate for the next two semesters.

"Hi Alice! You too! Hope your drive here was okay," Riley said to myself, my Mom and Dad as we continued to unpack my stuff into the small dorm room.

------------------------------------------------------------------------------------

Just like that we had finally met. Honestly, initially meeting Riley wasn't the thing that I was super worried about, it was the sharing of vulnerable information about myself that gave me a little pause. I was very open about the fact that I was trans, however, the possibility of Riley being unwilling to live with me on the basis that I was trans, was a really upsetting hypothetical to entertain.

I had intended to ask her over social media, before we ever met in person, but I guess the fear of rejection was on my mind then, just as it was on my mind now. The anxiety was really getting to me and as soon as both of our parents left, I couldn't help but pull the band-aid off.

"Hey, I know we just got here and everything, but I was hoping I could tell you something kinda big and important," I said.

Riley had a look of shock on her face. "Okay, sure," she said.

"I wanted to say something before all of this, but I was just too nervous to say anything and so here it goes," I said before taking a long pause. "I'm trans."

There was a pause as Riley processed the information.

"So like you're transitioning to be a guy?" she asked.

I was taken aback. I didn't expect this. "No, no. I was born a guy and now I'm a girl," I said.

"Oh okay. Cool," Riley said.

"That's it?" I asked.

"Yeah, I don't think it's a big deal," she said, "It's still fine if you're naked in the room by the way. I don't mind."

"Wow I really did not expect this," I said, still reeling.

"I hope you feel better now, I can tell you were a little anxious about telling me that," Riley said. "I bet you've been through a lot and I appreciate you confiding in me."

I felt some tears start to come to the surface, but I pushed them down.

"Seriously thanks for saying that," I said. "Not everyone is so cool."

Riley chuckled. "Well you haven't seen all the sides of me yet, so I wouldn't think so highly of me."

"Well you couldn't have gotten off to a better start," I said with a smile. "Were you hungry? Did you wanna go grab something?"

"Sure!" Riley replied enthusiastically.

------------------------------------------------------------------------------------

After Riley and myself both collected our food from the counter, we both had a seat across from one another.

"So what sort of stuff are you hoping to get up to, here at school?" asked Riley.

"Ya know, I'm not really sure. Obviously I have true freedom for once, but I was never really wild back in high school. Maybe... Maybe I'll try and see what it's like to be a little crazy," I said with a chuckle.

"Ahh," Riley said, "You're looking for a real college experience."

"I don't know, I guess?" I continued. "I didn't get a high school experience that I would say is typical -- because of transitioning -- and so now I guess I just want to do what a normal girl does. And by my estimation, that is going to be to go a little crazy, but we'll see if I have the energy for all that."

"Yeah I guess going through something like that, would shake things up and not feel normal, right?" Riley asked. "I like to think it was normal, just not the typical thing that happens," she continued. "I suppose my life up until now has been rather typical, but I'm still not sure I've enjoyed it too much. There's always drama and stuff happening that makes things feel impossible. I'm just glad, like you said, that I have freedom now. No parents, no siblings -- just me trying to figure out who I am and who I want to be."

"Well I can relate to that," I replied. "I only knew I wanted to be a girl, I never thought beyond that. Now that I am, I honestly just feel so overwhelmed by everything and all of my options, I don't know what to do."

"Riiiiiiiiiight!?" Riley exclaimed. "I'm supposed to choose now what I want to do with my life? Fuck that."

"Amen sister," I said.

We both bit into our food for the first time since sitting down. "I know this is out of nowhere," Riley started, "but would you want to go to a party tonight? I heard some people on our floor talking about it and I thought it would be a good introduction to college for the both of us."

"Yeah, that sounds fun!" I said enthusiastically.

------------------------------------------------------------------------------------

After finishing our lunch, Riley and I headed back to the dorms where the two of us proceeded to gather more information regarding the party that night. Turns out the party was going to be at one of the more reputable frats on campus, Delta Chi. It turns out their was also a theme for the party -- lingerie to be exact.

I was admittedly very nervous. Both about the party in general, and at the prospect of having to wear lingerie in front of other people. Most girls just had their own insecurities to worry about, and while I certainly had those, I also had a dick hanging between my legs that made wearing something like lingerie might expose my little secret.

Even though I am rather open about being trans, I still didn't really desire to let it be seen that I have a dick. If things progressed with someone so that we were intimately involved, I'd definitely want them to know, but I guess I always found it rather unattractive on myself, even though I didn't have any intention of getting any sort of surgery to remove it. I've always known my feelings on the matter were complicated and this scenario was really proving that to me.

That was exactly what I decided to tell Riley.

"Oh, well that's no problem," Riley said, "We can put you in something that obscures the vision of your lady parts. Luckily we're about the same size so you can wear the teddy I have."

"Oh smart," I said. "I would've just worn the classic bra, panties, and garter belt combo. Adding a teddy on top of that will definitely help me feel less subconscious -- less cold as well!"

Riley chuckled as she moved over to her closet in our shared dorm room. She took a minute looking around but finally emerged with a blue sheer, somewhat see through teddy and handed it to me.

"What about you, what will you wear?" I asked.

"Oh I've got plenty of options and ideas," she said. "I may just go with what you said to be honest though. It sounds sexy."

"No one has ever complained about it," I replied.

"Ohhhh, do you have some references?" Riley asked.

"Mayyyyybe," I said with a sing-songy voice.

Riley gave a half-laugh before asking: "So are we talking boys or girls here?"

"A little of each," I replied. "I'm not one to be picky. Though nothing makes me feel more like a woman, than being with a man"

"I know what you mean," she said.

------------------------------------------------------------------------------------

After doing our hair and putting on our makeup -- each of us opting for a smokey eye -- we both stripped down to nothing to put on our outfits for the night. I was wearing my favorite and only black lingerie set. Lacy and classy by lingerie standards. The only thing slightly trashy about it being the thong that accompanied it rather than standard panties. However, over top all of this was the aforementioned blue teddy that was lent to me by Riley.

Though before putting it on, I couldn't help but realize how nice it felt to just be naked with another girl and things not be sexual at all. It just felt like two girls -- two friends -- getting dressed for a night out.

I was drawn out of my daydream though as Riley slipped on a red body suit that was mostly see through, except where it being see through would create some awkwardness in a public area. Riley also slid some red fishnet stockings up her legs to match. She looked stunning -- model-like even -- and I was about to let her know when...

"Holy shit, you look so hot," Riley said to me.

I chuckled. "I was just going to say the same to you."

"I think we're going to have every guy in that party at our mercy when we walk in," Riley said. "But we are freshmen so we gotta look out for weirdos."

"Yeah," I started, "I think we're particularly vulnerable. And not just because of what we're wearing."

"How about you and me just stick together," Riley said. "I'm not interested in starting out college as the subject of a news story."

"Good idea!" I exclaimed. "Besides, I want to keep talking to you and getting to know you."

"Awww. You're so sweet," said Riley as she threw her arms around me, bringing me in for a hug. Without hesitation, I hugged back.

With an hour or so before people were going to start getting picked up for the party, this left Riley and myself with a little downtime. Riley opted to go out and be a little more social, while I hung out in the room just to recharge.

So far I was honestly very shocked how well things were going. I certainly didn't expect Riley to be so cool, both about me being trans, and as a person in general. I was starting to think that perhaps this was some sort of karmic act, as a result of all the good I'd done in the past, and the horrible things I had endured. But I was also very conscious that things could switch at any moment and that I could find myself in some rather dire circumstances. I obviously hoped things wouldn't come to anything like that, but I was planning on remaining cautiously optimistic.

------------------------------------------------------------------------------------

It was about 30 minutes or so until rides were meant to start arriving to take us to the party when Riley re-entered the dorm with a couple new girls.

"Alice, this is Anahis," Riley said, pointing to the gorgeous latina girl to her left, with silky long black hair, a perfectly made up face and an all white ensemble, complete with a corset that made her boobs look perfect, and a cute little tiara she was wearing on her head.

"And this is Chloe," Riley continued as she gestured toward her right to the person that had an asian complexion, with a similarly made up face, however, Chloe had opted for a very simple bra and panties look with a matching set of pink underwear.

"And we have booze," Riley said with a smile and holding a bottle of vodka.

We all moved to Riley's bed in order to sit and share the vodka, taking turns passing it around and taking a sip. Without a chaser, I was taking very small sips, plus with the added knowledge that there would probably be drinks at the party tonight, I didn't want to overdo it. All of the other girls, except Chloe, had the same idea as me -- pacing themselves so as to not get too fucked up too fast. But Chloe continued taking big sips, which worried me because she was probably the smallest out of all of us.

"Slow down Chloe, Jesus," Anahis said.

"I'm trying to have fun tonight," she replied.

"Well you're not going to be able to have fun if you're puking your guts up all night," exclaimed Anahis.

"I know, I know. Sorry. I'll slow down a bit," she said reluctantly. "I just want to fuck someone tonight, that's all."

"Well I don't think you need to be blacked out to do that," Riley interjected. "Look at you. You're so fucking hot. We all are. We're gonna be like the candy in a candy store tonight, except you get to be in charge of who picks you."

"Yeah, so don't let the alcohol choose for you," Anahis said.

"If I'm being honest, I don't really care who picks me, just as long as their dick is big," Chloe said matter of factly.

"How big are we talking?" I asked sincerely.

"I'm not sure," Chloe said, "My ex was like 4 inches and it was not very satisfying at all, so I want to give a much bigger guy a shot, so maybe, like, 8 inches."

"Oh no," Riley said, "You may be a little too small for a dick that big. It'll cut you in half."

"Really? I feel like I can handle it with the right guy," Chloe said.

"Well sure, but do you think a guy you find at a frat party is going to be all gentle with you? No he's gonna just ram it in you with no thought about how you feel. And with 8 inches of dick, it's not going to be pleasant," Riley said.

"Yeah I'd say work your way up to it, hun," Anahis interjected.

Chloe sunk deep into thought as she took a swig of vodka. And even though I had taken only small sips thus far, I was starting to feel a slight buzz come on and with that buzz, and all the talk of sex, I also could feel a warmth building up inside of me as a combination of intoxication and horniness emerged.

All the talk of dicks had my head spinning with images of me on my knees in front of a tall man and me worshiping his dick as he held back my hair. As I kept sucking I could start to feel him tense up as he was just about to --------

"Alice, are you ready to go?" Riley asked as she moved from her bed to the door.

"Oh yeah, sure," I said with the feeling of hotness now on my face.

------------------------------------------------------------------------------------

After the 4 of us were crammed into the back seat of some random Delta Chi brother's shitty car for the short 10 minute drive to the house, the 4 of us stood in our lingerie and light jackets outside as tons of other girls in lingerie, and guys in boxers poured in.

As we made our way closer to the house, we could hear music thumping and growing increasingly louder. As we stepped over the threshold, the music was nearly deafening, blaring some popular song from TikTok as tons of people danced in the main living room, and gathered drinks in the kitchen.

The four of us made a beeline for the drinks, as we began to cross through the dance floor, where girls wearing similar outfits to us were grinding their asses on guys and each other. With guys wearing just their boxers and the girls looking so hot, it didn't take long until I noticed that many of the guys were unashamed with the hardness of their dicks, literally popping a tent in their boxers.

Geez, I thought to myself. We're basically one step away from a giant fuck party with everyone out here on the dance floor dry humping each other in barely any clothes. As my eyes focused on one couple who seemed to be getting particularly physical and handsy with one another, I was jerked away.

"Here," Riley screamed over the music as she handed me a drink.

My eyes went searching again for the couple I was just looking at and found them. The girl, wearing a tight black bodysuit, was facing the guy and had one leg curled around him and was dry humping him while making out.

"Pretty hot, huh?" Riley yelled as she gestured toward them.

The both of us continued drinking as we continued to watch the couple dry hump right in front of us. After a couple more minutes of that, the girl took the guy by the hand and started to lead him towards the stairs leading to the second floor, no doubt to finish what they started out here in a more private place.

"Wanna dance?" Riley screamed over the music.

"Yeah," I yelled back.

As we made our way onto the dance floor, it finally dawned on me that we had been separated from Chloe and Anahis. Before I could think too much about them, Riley and I had reached a place on the dance floor where we could dance and so we started shaking our bodies together in rhythm with the music.

We didn't dance together like we had just seen that couple doing, but rather we were dancing like two friends at a wedding or any other place like that -- just two girls having fun. The fun, however, was soon interrupted when a guy slid behind me and Riley at nearly the same time. As we looked at each other, I gave Riley a shrug and proceeded to change up my rhythm.

Rather than focusing on my whole body, I started focusing on my ass, as I twerked on the guy behind me. As I pressed my ass into him, I could feel his dick start to grow. As the guy's dick became fully hard, he had to readjust so that his dick was pointing up, so as to not be crushed by my ass.

As we settled into a groove of me, basically jerking a guy off with my ass, I felt his hands hold my waist, as if he were fucking me. I looked over and made eye contact with Riley who was in the same position, shaking her ass just as I was doing. We both giggled at each other, before I saw a hand reaching for Riley's boobs.

Her eyes widened as the guy reached her boob and started to play with it. Once again the two of us giggled. Riley continued to let the guy feel her up when all of a sudden I felt a hand on my boob. I suppose seeing the bold display of heavy petting had gotten the guy I was dancing with, to make a move.

My eyes widened, just as Riley's had, and Riley and I once again shared a giggle. We continued making eye contact as we stopped giggling and were left with just the heavy petting and the grinding situation. As it continued, the guy groping my boobs was starting to hit the right spot and my eye contact with Riley became much more difficult as I started to close my eyes a bit and focus on the sensation.

"You slut," I heard Riley yell, but just barely. She then gave me a wink.

I replied with a smile, before I was suddenly turned around, as the guy that I was dancing with grabbed me by the hand and started to lead me where I had seen the couple go earlier. I turned to look at Riley one last time, as she gave me a questioning look and a thumbs up, signaling to ask if I was okay.

I gave her a nod of approval and a smile back.

The guy I was with led me upstairs and after trying a few doors, but with no luck, we finally pushed our way into a room -- a bathroom.

As we entered, I had one thought on my mind, and immediately sank to my knees on the bath mat to give my knees some cushion.

The guy, after closing the door and locking it, turned around to the sight of me on my knees and uttered one word: "Slut."

He then, without hesitation pulled down the only thing he was wearing, his boxers, to reveal the dick that I had been grinding on for the past 15 minutes. It wasn't bad, honestly nothing to write home about, but kind of the perfect size for giving a blowjob.

The head of his dick was glistening with precum, proving that I was an expert at teasing a guy, and in my eagerness, I moved my hand up to his cock to use my finger to get some of the precum and put it in my mouth.

After getting a taste, I immediately moved my mouth to his cock and began sucking, fulfilling the fantasy I had earlier that night. It made me feel so hot to imagine the sight of me on my knees in my lingerie, with a guy's dick in my mouth. Moving my head up and down as he moaned.

The guy put his hand gently on my head, as I removed my hands from him so that I was just using my mouth. I started to move them to bunch my hair up and was going to try for some sort of messy bun, before he grabbed my hair for me so that it wouldn't be in the way of the blowjob I was giving him -- what a gentleman, I thought.

I didn't take too much time to focus on that though because I was intent on making this guy cum. Just as I suspected it wasn't going to take too long to do that. The 15 minute dry humping session had this guy sufficiently horny, so that after about 3 or 4 minutes when I looked up at him, he was looking up with his eyes closed, trying so hard to prolong this experience.

But that only made me work harder as I picked up the pace and sucked in just a little bit to provide a little bit more a tight suction around his cock. I could tell it was working because his face started to scrunch up and I could start to feel his cock get even harder.