Becoming a College Cuckold Ch. 01

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?"

"I've been talking her ear off about you since before I even asked you out at the coffee shop. Trust me. You have nothing to worry about there.

"Nothing to worry about because she's not interested in you?"

"Hey!", and I was a little wounded by that. But she had good reason to have that view. Rachel was classically beautiful. 5'8, blue eyes, thin with perky c cup breasts and an ass that, and I'm being honest here, would put Mia Malkova and Anikka Albrite on notice. She was also blond, which made her your All-American beauty. Totally different than Gabriella, but damn. And while it was true I had never done anything with Rachel, I had lusted after her and doted on her for years as her best friend. But at the same time, I was totally committed to Gabby. If I'm honest, Gabriella was a bit of an achievement for me. It felt validating. I was excited to show Rachel that I was worth dating, and that Gabriella recognized it.

I should have known better.

That summer raced by, and while I only saw Gabriella one weekend (and had sex for the third time!) when Rachel and I picked out our apartment and put down our deposit, we spoke on the phone every day. I was working an internship and then another job for money on the side, so there wasn't much time for craziness. I found myself watching a lot of porn, of course, particularly of young hispanic girls that looked like my Gabby. And, sure, okay, Rachel look-alikes were always popular. I found myself thinking over and over of Gabriella telling me that her two previous boyfriends had big cocks, and I loved watched porn where a little hispanic girl would slobber all over a huge cock before getting pounded.

One night, while on the phone with her, I had to bring it up.

"So ... babe ... remember how you told me you don't really like giving head?"

"Well, I mean I guess it's not that I don't like it. I just have to be in the mood and all worked up."

"Oh. Okay. Well, the guys you've done it to. Did you like their big dicks?"

"Ugh, guys are so silly getting worked up about dick size. I'm not doing this with you."

"No! Babe. I'm not mad. It's ... kind of hot to think of you as being sexual. Did you give them head a lot?"

"Are you sure you can handle this?"

"Hey ... we're together now, right? I'm not worried about the past. We're still getting comfortable with each other and I get that."

She sighed into the phone. "Well. Yeah. I mean, there were times I really got into them. That's why I was with them. With guys that are bigger, stronger, you just ... I guess sometimes you get wrapped up and want to please them. But you know me. I don't talk to guys that often and really let loose. It's hard for me to trust people."

"Why is that, by the way. I think you know how hot you are."

"Funny you're just now interested in MY wants and needs. John, both guys ended up cheating on me. I was just another slut to them."

"Babe. I'm sorry," I said. "I'm a dick." And then, "you know I'd never do that."

"I know. But you know what the worst part was? The second guy, was fucking other girls the entire time. And even after I found out, I went to his house, sucked the life out of his dick, rode his cock, let him take me from behind. Everything. I still wanted him. Let him cum in my pussy. Even after what he did to me I was still drawn in to him and his dick. So I knew I had to stop. And you were the first guy I opened myself up to in three months before you asked me out."

My dick was somehow rock hard from listening to her describe what kind of slut she had been, and I was totally speechless.

"He came in your pussy?"

"Well I'm on birth control, you know that."

She made me wear a condom, even though she knew I had little to no sexual experience. Just like her comment about the big dicks weeks before, this one would gnaw at me for some time.

"Oh. Yeah," I said lamely.

"Look, are you going to be weird about this? It was before I met you."

"No! No, babe, I brought it up. I would never hold something against you that happened before we knew each other. And I'm so happy with you now."

"Same, John. You've made me feel like I can trust guys again."

About a week before moving in for sophomore year, Gabriella started to come off as distant in our daily phone calls. I couldn't tell what it was that was wrong, but something definitely changed in her voice. I was terrified that she was sick of me, or wanted to move on. I should have made more of an effort to visit her over the summer, but I wasn't exactly sure where I could have stayed. I worried for a week, though she swore nothing was wrong.

The first night back, she couldn't deny it any longer. I had been hoping for reunion sex, but the distance she was putting off kept me discouraged.

"Gabby ... I promise I won't be mad but you have to tell me what's wrong. You can't keep saying nothing."

She was silent for a moment, not looking at me. Rachel was in her room unpacking, and Gabby and I were on our own. I was so excited about the privacy we were going to have with me having a whole room to myself, but if my girlfriend was going to act like this ... well, I didn't know how fun it would be. Finally, she opened up.

"Okay. Last week I went out with my cousin. You know I never drink but I felt like I could let loose a little bit. I don't get the college experience at the junior college that you do at university. Well. I met a guy and I fucked him. I feel awful. I don't want to lose you. It was just sex, I ... can't explain myself."

She wasn't crying, but was speaking more as a matter of fact.

"Were you drunk? Did he take advantage of you?" I was clinging on to any kind of hope it wasn't her choice.

"I had a few drinks, but it's not worth lying to you. I just ... I was horny, I thought he was hot, and it happened. It was stupid."

I felt like I had been punched in the gut. My beautiful Gabriella had done this to me? I realized I had more questions.

"Well ... what was he like? Was it just the one time?"

She didn't respond immediately. "I ... I told you I was attracted to him. We fucked that night. It happened again the next morning."

The room was spinning. "What ... was he big? Is all that happened that you fucked him?"

"He wasn't small but I've tried to tell you that's not everything. I sucked his dick that morning too to get him going."

"Are you like ... into him?" I asked. "Have you talked to him since?"

"No. No. I want to be with you. I don't even have his number. Now that you're here, I'm so excited to be committed to you. I know we're young but I've never trusted anyone like you."

She put her hands in mine, which were resting on my lap as we sat on the bed. All of a sudden I noticed something, and she noticed something at the same time. I was hard. Her eyebrows raised. I felt disgusted, betrayed, and ashamed that I was ... turned on.

"I ... I don't know," I said. I stood up. "This. This is a lot. A lot to take in. I'm pretty sure I'm in love with you. I don't want to lose you. But this is not normal."

"I love you too! I know I've messed up." She walked towards me. "Can I make it up to you?" She gave a half-smile, as though she couldn't believe she was trying it instead of being thrown out of the apartment. She placed her hands on my cock through my shorts.

She said, "I know I need to do a better job of taking care of you. I need to start opening myself up to you." She was jerking my cock. "You need to have more opportunities to see me. To be with me. I need to play with your dick, and make you happy. I'm ready to give more of myself to you."

She had pulled down my pants and was massaging my dick while she talked.

"Do you like how I stroke your dick with my hands? I know I've been a bad girl. I want to be your bad girl. I think your dick likes this."

"I .. I do." I was trying to be mad at her, I was trying not to think about her being a bad girl with guys with bigger cocks than me. But mostly I was turned on. After a short while, I couldn't take it anymore, and I exploded all over her hands.

"That's my baby. That's a good boy. I'll have to get my mouth involved next time."

I was lightheaded from the orgasm and the events and had to sit down. She went to the bathroom to wash her hands. I used a tissue to clean up the rest. We cuddled up and watched a romantic comedy before falling asleep.

At one point, she said "Baby ... I really am sorry. From now on I want to make sure I'm your bad girl."

I had no idea what I had coming.