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Here's another one from back in college. I had been dating a girl for a few months, let's call her Vicki. The relationship had gone from 0 to 60 in no time flat. The night we met was at a friend's show. I didn't notice her until after the show was done, but I ran into her sitting on the steps outside chatting with some of her friends. She was medium height, about 5'6", long blonde hair, lots of freckles, thin build but nice C cup breasts. She smiled at me when she saw me coming and I decided to chat her up.
Long story short we decided to hang out the rest of the night. We went to a movie and just made out in the back row. Afterward she came back to my room and we just went at it. But this isn't a story about her. The relationship went nowhere, it became clear it was only about the sex for her. As things got stale I decided to end it and move on.
Afterward, all her friends got really frosty right away giving me nasty looks anytime they saw me coming. I wasn't shocked, breakups mean tearing apart your ex and you have to support your friends. nbd. However, one of her friends wasn't on board with the rest of the group. Let's call her Madison.
About a week after our breakup I ran into Madison in the dining hall. Madison is another blonde friend of Vicki's, shorter than her with much bigger breasts, who lived next door to V. It was the first time we'd crossed paths since I had split up with Vicki, and while everyone else had been staring daggers at me Madison was the friendliest she'd ever been. When V and I had been dating she was casually nice, but we had barely exchanged more than 20 words. Now she asked to join me for lunch and was throwing me all the signs, touching my arm, playing with her hair, big smiles, chatting non stop.
The whole conversation she doesn't mention Vicki or the break-up, she's just asking about me and talking about other things going on around campus, or complaining about sharing such a small space with her roommates. I mention that I wouldn't know about that, since I have a single. She immediately jumps on the topic and asks if she can see my room.
I'm not an idiot, and I can see where this is going. I say "yeah, sure, do you want to see it now?"
Again, she jumps on the idea and the next thing I know we are heading back to my room in the middle of the afternoon. As we get closer and closer to my room I can see her getting more and more nervous as her confidence starts to fall apart.
Once we get there I close the door behind us. Though it's a single the room itself is a small space so she shyly stands in the middle and looks around taking it all in as this blush starts to grow on her cheeks. Seeing how shy she has become I take the lead, step up to her, take her chin in my hand, turn her to face me and kiss her. She's a little stiff at first but she quickly loosens up and wraps her arms around my neck. She gets more and more into making out, and so I go farther. I reach under her skirt to squeeze her ass, and then slip my fingers inside her panties to play with her pussy which is already soaking through the fabric.
Since all this was fair game and she hasn't stopped me yet, I figure we might as well go all the way. I push her back onto the bed. I yank off her shoes and socks and then she excitedly helps me take her panties off. I love eating pussy and hers was so deliciously tight and pink. As nervous as she had been I thought it might take a while to get her off but maybe a couple minutes later she cums hard with my mouth on her clit and fingers deep inside her.
She's calmed down at this point and is feeling more comfortable in the afterglow. She asks if I have any condoms and I gesture to my desk drawer while I start to get undressed. She fumbles around in the drawer for a moment and pulls out the box of condoms I have in there. "What are these?" she asks holding up the box of my.size 64s. She turns around as I'm sliding off my jeans and underwear and her eyes bug out. "What the hell is that?" she asks, gesturing toward my crotch.
I was honestly a little surprised at this, since I figured the reason she chatted me up was because she had heard something from V. I asked her as much and she said "She joked about it being big but I thought she was just exagerating. That thing is ridiculous!"
"Is that a problem?" I ask her. She says "No, I don't know, maybe."
"Let's give it a try and see how it goes." I suggest, and she agrees. She opens the box of condoms and she's incredibly nervous again, dropping the condoms all over the floor. She picks them up and her hands are shaking as she opens the wrapper and puts it on me. I can tell she's losing the plot a little as she starts stroking it in the condom, her eyes fixated on it as she plays with me. So, I push her back onto the bed and start to tease her with it. Rubbing the head on her clit and sliding the length of it along her slit.
Once she's good and turned on again I start to work my way in, a little at a time. She's a little too tight, and even as wet as she is we need some lube. I'm gradually able to work a good amount of my dick into her but I'm still giving it to her nice and slow while she alternates squeezing her eyes shut or staring right into mine.
Feeling good about how she's taking it I decided to start picking up speed and see how deep she can take it which she does surprisingly well with. She grabs one of the pillows from behind her head to hold it in front of her own face as she starts shouting the usual "fuck me" and "oh god." I was sad not to see her face or kiss her, but the view of her big tits bouncing was great anyway.
We end up going at it for a while until we've both cum. And after I pull out of her she surprises me by taking the condom off to start sucking my cock, almost like she can't help herself. We end up going another round and afterwards just laying in my bed and chatting.
She admits that she had a crush on me before but only knew me as V's bf. "Sometimes I'd hear you two in her room together and I would play along, imagining you were with me instead of her" which explains why she was so shy before.
We hung out a few times after that, but only when her other friends weren't around. She didn't want to get ostricized for betraying V. She at least didn't join them in staring daggers at me, but we mostly kept our distance from each other in public.
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