My (f)riend's brother at the de(m) convention | 2016

LONG SORRY A little backstory: I went to the DNC in Philadelphia and my Airbnb fell through for various reasons, and I ended up having to crash at a friend from back in Maine's house in the area. She was still up there, so the only person home was her brother, looking after the huge, eccentrically designed stone house. Really a crazy place.

Even quicker backstory on me: I'm 19 and 5'3" with wavy short brown hair, curvy body. Thick thighs, big butt, 32DDD boobs, but small waist. All in all 135 lbs if that helps. Gray/Green eyes if anyone cares :)

So I arrived late at night with my bags and my brother and dad. We were introduced to Tanner, the brother. He comes from a Quaker family, so he has a beard that speaks to that, almost Amish looking. Light brown hair, tall sturdy build. Around 25. He had a very calming presence about him, and was excited to show us to our rooms. My brother and dad went to their beds and almost immediately fell asleep. I couldn't help but notice that he gave me the room furthest away from my family as possible. It was clearly the best room, belonging to my friend, but it was interesting that he offered it to me most enthusiastically.

After they were in bed, I asked Tanner if he smoked pot. He held up a finger to me and scurried into his room and out again, holding a homemade bamboo bong. He proceeded to give me a tour of the house and his favorite smoking spots. He kept sneaking glances at me and my reactions, and we were giggling the whole time. We decided to watch a movie, so he downloaded it while I took a shower, but I fell asleep before it was done (damn internet).

The next day, I came back from a long day of protesting in the hot sun. After another shower, we decided to sit down and watch the movie with my family. (Ponyo if anyone is interested.) Our hands kept accidentally touching when we shifted positions and I was getting really excited when they did. The fam went to bed about halfway through, and it was just the two of us. We looked at each other, and immediately switched into a cuddling (head on shoulder, arm around) position. I could tell that he'd wanted to do that the whole time like me, and it was exciting. I started falling asleep, but when the song at the end started playing I opened my eyes. I looked up to see him looking at me with the sweetest look on his face. Then we both just sort of leaned in and kissed. And then we kissed some more. Then all of a sudden we were rolling on the couch, me putting my legs around him while we made out passionately. We pull away for a breath and he says "relocate?" I nod, and he leads me to the room that I'm staying in (his was right next to my dad's). We pick up where we left off, and before I know it both of our shirts are off. Then my sleep shorts. As soon as he gets those off, he sort of groans a little bit and asks me if it's okay to slap it. I giggle and say yes, and so he takes a big handful of my ass and just grabs me all over. Then he gently slaps it, then massages and grabs it again, all over my ass, like he couldn't believe what he was experiencing. It felt so good, especially after walking all day. Then his hands started wandering, fingers going into crevices, gently exploring my curves. All of a sudden his eyes light up and he grabs me by the legs, picks me up and puts me onto my back. From there he kisses up my thigh, stopping right at my upper inner thigh area that's so sensitive. I start squirming a little when he breathes gently onto my skin. He then looks me in the eyes while goes back down and starts up the other leg, doing the same thing. Finally he breathes hot breath onto my neglected, wet pussy. He takes two fingers and gently separates my lips to see how tight and wet I am. He does the little groan thing again before slowly sticking out his tongue and gently flicking my clit a single time. A sort of shock wave of pleasure courses through my body and I can't help but sort of lurch. He then takes one long lick from my taint up the entirety of my vagina until he reaches my clit again, causing another lurch from me. He then reaches up with one hand to grab a pillow, and sticks it under my butt. He giggled a little bit at that, saying "you barely need it". With that he makes eye contact one more time before going in. I don't even remember specific things, but I remember riding the edge of orgasm the entire time, practically panting. I held onto his hair for support, and occasionally scratched his back if he was doing something particularly wonderful. Of course I was heavy breathing the entire time, sometimes letting a moan escape, but trying to stay quiet in case the walls were thinner than I thought. After a little bit, Tanner came up for air and the look he gave me was absolutely animalistic. I greeted it with the same energy, and I practically tore his boxers off. What was underneath I honestly was not expecting. I've had a large penis or two in my day, but this one slightly outranked even the biggest I'd had before. My jaw visibly dropped a little, and he giggled a little before embracing me again, and taking my lower lip gently between his teeth.

I couldn't contain myself and kissed down the entirety of his body before reaching the cobra of my intentions. I took it into my mouth and swirled the tip with my tongue, tried to get it as deep down my throat as possible, all that good stuff. Then he picks me up again and essentially throws me down on the bed. He quickly put the condom on and grabbed his bottle of lube, holding it up for my approval before putting some on his finger and softly traced up and down my already dripping parts. He of course put some on himself with his other hand, and the look he gave me while doing this was almost ravenous.

I positioned myself back on the pillow, and he repositioned himself between my legs. I was excited but also a little nervous about the size. He must have seen that on my face because he leaned in close to my ear and said "just let yourself relax." I did what he asked, let my muscles relax in preparation as he rubbed his tip against my throbbing clit, and up and down my opening. Slowly, steadily, he worked himself in, gently breaching my tight wet pussy with his monster cock. It didn't hurt as much as I thought it would, but it certainly helped that he had a reassuring hand by my head, and that he was barely rubbing my clitoris, teasing me into opening up for him. The feeling of him filling me slowly, stretching me more than I've ever been stretched, was absolutely unbelievable. My back arched slightly, and I had to grab his hand and put over my mouth so I didn't make too much noise. Eventually, he got to a point where he couldn't fit anymore of himself into me comfortably on my end, so he just stayed put, letting me feel his hot huge cock pulse fill me as much as I could take. Then when I couldn't stand it any longer, I slowly started rocking my hips, working him a little in and out of me. Then suddenly he put his hands firmly on my hips, holding me in place, and he started working himself in and out me, using sort of circular motions. I started to do the same sort of thing to meet his movements, and this time he let me move. He started rubbing my clit again, and before I knew it, he was almost working his full length into me when I came all over his cock. He stayed put while I did that, letting me work myself feverishly onto him, rubbing my own clit while he kept my mouth quiet with his hand. I scratched his sweaty back a little while waves of pleasure crashed through my body. After the waves subsided, I lay there panting and sweaty underneath him, loving his weight on top of me. He gave me a minute, waiting still inside of me, before slowly starting to move again. We repeated this cycle a few times, him lasting the entirety, before I collapse underneath him, begging for a breather and some water. He laughs and collapses as well, even sweatier than I, next to me on the bed. We drank some water and he ran his hands over my body, stopping to massage my sore thighs and feet (ugh dreamy). After 10 minutes of this, I say, "I'm so sore but I want you so badly" and he only responded by kissing me passionately. This time he stood next to the bed, lining up perfectly with my slightly worn, sticky pussy. Still hard, he puts a little fresh lube on himself before starting to push gently into me. I beg him to go slow, but this time my exhausted parts are so sensitive, that I can feel an orgasm building just as he enters me. Slowly entering me deeper, I start rubbing my clit and saying "oh fuck" gently to myself when I can feel the pressure and pleasure actively building inside of me. He continues his slowly course, working his huge length patiently into me. Finally I can't help myself and I grab his body closer to me pulling him deep into me, and proceed to viciously grab onto him as every muscle tightens around his hefty member inside of me, cumming harder than I've ever came before. I squeeze him so tight without even trying, and my nails dig into his back as I can't control my moans any longer. I almost squeak into his chest when I bury my face into his chest hair, grabbing it, anything on him to keep me grounded. He was grabbing me just as hard, burying himself deeper into my pussy than ever before. It lasted for what seemed like minutes, and when it finally subsided we were beyond words, just trying to gather our thoughts and catch our breath. We lay there for a while before recovering slightly to change position to trace each other with our fingers while we passed out intertwined.

We woke up when my dad knocked on my door to tell me to get ready for the day. I opened the door only a crack, still naked, while Tanner hid in the bathroom, and he seemed suspicious of the scene, but after being reassured by me, he left, letting Tanner and I collapse into nervous laughter on the bed, kissing until we had to actually put on clothes and such. We snuck kisses until I had to leave. I may not see him anytime soon, and my family will ever know, but it was not a night that I'll forget anytime soon.

TL:DR had best orgasm of my life in my friends bed with her brother, with my family sleeping close by.