My first time doing it with someone else.
When I first started college a year and a half ago, I was set to share a room with two other girls. To my relief, one of them chose not to attend at the last minute, leaving a room for three girls to only two.
Aside from actual academic concerns, my biggest fear about college was masturbating. I had never talked with friends about it and there was no way I was bringing it up with my roommate. At home, I would either lock my door and do it in my room, or do it in the shower. In addition, I found it really hard to get off unless I could get completely naked.
At first, I was hopeful that I could at least get some privacy in the bathrooms. Unfortunately, they were shared by everyone on the floor. They stunk, and the showers were cold and uncomfortable. There was no way I would be able to finger myself in there.
When I met my roommate, she seemed just as shy as I was. Her name was Elizabeth. She had long straight black hair reaching to her mid back and thick glasses. She was incredibly thin. The first few days we were there, we didn't have any classes, and it was hell.
We talked for a little while on the first two days. She was into video games and anime like me and she didn't really know anyone else at the school, while I had a number of high school friends there. She seemed perfectly nice and I figured we could get along.
Elizabeth did not leave the room for anything but the bathroom. She spent three days straight sitting on her bed using her laptop. I explored the campus, but every time I returned to my room she was in the exact same position. One time I was a bit daring and pulled my shorts and panties down when she left for the bathroom, but I had to scramble and dress myself when she returned only minutes later.
By the first day of classes (fourth day on campus), I had resigned myself to quietly fingering myself in my pjs under the covers in the middle of the night. And even then, Elizabeth barely slept. She stayed up on her laptop until like two in the morning, and even after she closed it and got under the covers, I could hear her tossing and turning most of the night. I would freeze every time she made a noise. It was hell.
Then everything changed on day four. I got back from class and she wasn't there yet. I decided to risk masturbating. Of course, like five minutes in, I heard the door unlocking and had to dress myself quickly. She rushed in and threw her books down.
That's when the most wonderful words left her mouth. 'I'm going out with some kids from my lit class. I'll be back tonight.'
She would be gone. For HOURS. Needless to say, I had a lot of fun while she was gone. I pretty much soaked my sheets in juices. By 8:00pm, I was all jilled out, had dressed myself in my pjs (t-shirt and short shorts) and was just lurking on the internet.
Elizabeth got back around 8:30pm. As she closed the door behind her, Elizabeth was making some kind of sound like moaning. It took a second to register that she was wearing nothing but her shoes, socks, and an oversized sweatshirt. She was literally dripping between the legs.
Before I could say anything, she looked at me blushing and said 'Sorry, I really need to do this. Please don't watch.' And she lifted the sweatshirt high enough to expose her soaking wet pussy and started to go to town on herself.
She had two or three fingers working, two inside her lips and a third massaging her clit. It was the most amazingly hot thing I had ever seen.
All I could think was that I should leave or look away, but I could feel a wet spot forming in my panties. About three minutes in, I gave in and dropped my shorts and panties, then placed my own fingers in the same position. At first, I crossed my legs and tried to cover myself with my opposite hand. I was insanely embarrassed that I was doing this in front of Elizabeth. But once I had been going for a few minutes I stopped caring and spread my legs for the world to see.
We went on like this for a good ten minutes before Elizabeth let out a huge moan and froze up, then slid to the floor, landing in the miniature puddle she had made at the foot of the door. About a minute later I felt my own climax wash over my body.
We sort of just sat there for a few minutes, awkwardly looking at each others' cum-stained crotches and our matching puddles. Then, as Elizabeth got up to get some paper towels, I decided to break the tension 'That was hot...'
Elizabeth blushed even harder and pulled her sweatshirt lower to cover herself. She told me she thought the same about watching me and that it was also her first time doing it with someone else watching, let alone joining in.
After cleaning herself up and putting her pjs on, she explained to me that a male friend of hers was messing with her (entirely consensually) and had gotten her really horny. On the way back to the dorm, her new friends dared her to streak back to our room, but she talked them down to letting her wear the sweatshirt. Already horny from the teasing, one of the other girls decided to fondle her a bit to get her dripping for the run. By the time she reached our room, she just couldn't wait any longer.
Since then, the two of us have been way more comfortable about masturbating. We just start doing it with each other in the room, usually completely naked. We even do it together sometimes.