My sophomore year of college was the beginning of major changes in my life, and it's crazy to think about how things spiraled out of control as fast as they did. My name is John and I go to a university in Miami. I had a successful first year in the dorms but they tend to be more expensive than living off campus, and while I wasn't much for parties, I was excited to get away from overzealous RA's. My scholarship covered my tuition, but I was going to need a roommate and some loans to cover the cost of an apartment.
A bit more about myself: I'm not a bad looking guy, but I've always been fairly awkward around girls. I have an average-sized dick, or at least that's what I tell myself. It's five inches. I've never really felt bad about it. I've had sex with two girls, the first a girl from band in my rural hometown a couple hours away, and now my current girlfriend Gabriella. The first girl was also a virgin, and it was a one-time thing. Really, we both sort of just wanted to get the virginity thing out of the way and it happened at one of the few high school parties I drank at.
Gabriella is also 19, and goes to community college around here and is a barista at one of the campus coffee shops. She grew up around here, and is definitely someone that I think a lot of people would consider out of my league. She didn't come from much money, and was perhaps a bit of a late bloomer. She doesn't have the most confidence about her looks, then, but this is completely ridiculous. She's half-white, half-hispanic, about 5'3, and weighs about 120 pounds - and a lot of that is in her tits and ass. Her natural double-D chest is something I catch myself staring at pretty regularly, even if she doesn't show it off as much as I'd like. To be honest, though, if she did I feel like I might lose her.
She's fairly shy, and after nearly a semester and a half of studying at her coffee shop, I had the courage to ask her out. She said yes, and we dated for the rest of the semester before I went home for summer break. Our first time having sex, the second time of my life, was the night before I went home. She hadn't given me so much as a blowjob before then, even though I had spent a lot of time fingering her and going down on her. She said sucking dick just seemed icky, and that the two boyfriends she had been intimate with before me pushed it way too often.
She also said something that made me a bit nervous.
"Look, babe, I just am not really interested in sucking dick. It's annoying when guys ask for it, it's icky, and my past boyfriends were pretty big and it just wasn't easy at all. We're still working up to have sex, but I promise I'll make it worth it when it happens. Just don't be needy in the meantime. It's not attractive."
Wow. Okay. So her past experience was with guys with big dicks. When we finally did make love on our last night before break, it was sort of overwhelming. She had bought special lingerie for the occasion, and showed up at my dorm in a trenchcoat and her hair in a ponytail. My freshman roommate had already gone home, so the place was all me. I didn't know if we would watch a movie or go out to dinner or what, so you'll imagine my surprise when she entered my room, untied her hair, and dropped the trench coat on the floor.
Thigh high black stockings, crotchless black thong panties, and a black bra to match, and that was all. Oh, and three inch heels.
We immediately started making out, and I felt like the luckiest man alive as I groped her huge tits and reached back behind to get a handful of her ass. We took it to the bed and I started to move down, kissing her neck, and then chest, and then sucked on each tit. She was into it, and I was encouraged. This was a far cry from my only sex act back in high school. I ate her out for three or four minutes, and my cock was throbbing despite the fact that I had jacked off just a few hours beforehand.
Finally, she asked if I had a condom, and I slipped one on. I couldn't believe my good luck as I slid into Gabriella, and felt proud as she gave a slight whimper as my dick went in. We were going in the straight missionary position, and I had no clue how long I could last.
"Oh, oh ... fuck me really good John. Oh ... this is so good ... keep going."
I asked her if she wanted to try a different position.
"I ... just keep going ... just keep going."
I had sort of wanted a reason to pull out to slow myself down and keep myself from coming into the condom, and I also wanted to fuck her from behind. I can't tell you how good her ass looks in jeans and a thong, and it would have been an amazing feeling to give it to her doggystyle. Without her permission, though, I did keep going. At least for another 15 seconds. I couldn't hold on. All of a sudden I was coming, and I let her know.
"Oh, babe, babe, I'm coming. Oh my god. Oh my god I'm sorry. You're too good. You felt too good."
I saw a small look of disappointment on her face, but she masked it quickly and pulled me down so I was lying flat on top of her, my deflating dick still inside the condom that was still inside her.
"It's okay baby. Kind of makes me feel good to know my pussy is that good for you."
I smiled, feeling a little better, but knowing three minutes would be something I'd want to improve on. She found some of my sweatpants and a t-shirt and we watched a movie and ordered pizza. It was perfect, though we didn't end up having sex again that night. She said she was tired. There was one other thing that I knew was bothering her, and something we would end up reckoning with.
"So, tell me again ... what's your roommate going to be doing when you live with her next year?"
Ahh yes. My new roommate. It was completely fair that Gabriella was worried. You see, while I had made some friends that I would have been able to live with as a sophomore from the university, my best friend from home, Rachel, was going to be moving from our town to Miami and it was going to work out perfectly in terms of both of us needing someone to live with.
"Rachel just needs to get out of our town. I've told you how it is. If you don't leave, you're stuck. She knows I can be a good support system for her, and she doesn't necessarily have that at home either. I think her plan is to move here, get a job, and then eventually get started at the community college, like you. Her mom at least promised she'd cover the first six months of rent for her."
"I see," Gabriella responded. "And you two have never had a thing? I've seen the facebook. And I've heard the way some of your friends talk about the weekend she came and visited. She's hot, she's apparently down for whatever ... is that you? Is your apartment going to be a madhouse?"
"Gabby ... we've never been a thing. Rachel and I. That's just not what it is. Frankly, I'm probably in what people would call a friendzone. We've just always told each other everything, from boys and girls to sex ... okay, well, more her sex than my sex ..."
And we both started laughing a little bit.
"So you really don't have feelings for her?"
