I finally pulled together the courage to talk about this, so feel free to tell me what you think.
Ok, so all of this happened about two and a half weeks ago. Just for a bit of background, I'm a college sophomore, five feet one, pretty damn petite, have fairly short brown hair, and small b cups which I'm quite fond of (let's face it, everyone reading my description would be up in arms if I didn't mention my boobs). At the point when this story took place I had broken up with my boyfriend of about four months a few weeks previous and was kind of looking to do something a tad wild and out of the ordinary to help me get over the breakup. When one of my friends invited me to a party at a house a few blocks off campus I wasn't thinking of doing anything particularly crazy, but the night had other plans for me.
When we first got to the party I was actually feeling pretty damn uncomfortable; my friend had slipped off to dance, leaving me alone, and the house was packed to the point of being unpleasant. I was actually considering leaving within the first ten minutes when I bumped into a guy I knew named Dan (not his real name of course, wouldn't want to betray his privacy). We knew each other from one of our classes, we weren't exactly the closest, but had chatted a couple of times before lecture started and thankfully for me we started to hit it off fairly quickly. We ended up finding a semi quiet corner and continued chatting over some of the 'punch' the host had put out (god only knows how much booze was in that stuff). Now I can't lie, Dan was very much the kind of guy I find to be attractive, tall, somewhat lanky, and most importantly charming as all hell without being self absorbed. As we chatted things became increasingly flirty and eventually some light making out started. I was kind of embarrassed about kissing in public, so I suggested we move back to my dorm room (thank god for having a single).
As we were walking back to campus I was equal parts nervous and aroused; on the one hand I had only been with three guys in any capacity before and had never had anything resembling a spontaneous hook-up, but on the other hand Dan was pretty much my dream guy. By the time we got back to my room I was almost shaking with anticipation and seriously turned on. As soon as the door closed I pulled him in for a huge kiss and we stumbled over towards my bed. Now, to Dan's credit, he was the perfect gentleman in bed. Neither of us had a condom which put sex off the table, but he still took his time undressing me, kissing all over as he peeled off my shirt and pants. By the time he had me down to my bra and panties I was practically squirming, I hadn't expected the situation to be so sensual and tender, both of which were major turn ons (guys take your time and be gentle, trust me, it works). I got him undressed and he asked me gently if I was ready to go further (GOD YES), and with that he helped me out of what little I had left on.
When his fingers first swept down over my waist and to my clit I thought I was going to orgasm on the spot... which I pretty much did. I don't think I lasted more than two minutes before him just stroking me lightly sent me over the edge. After giving me a minute to catch my breath, Dan slid two fingers inside of me while he worked my clit with his other hand. I've learned since that he had only been sexually involved with two people before that night with me, but my god whichever girlfriend of his taught him to finger her taught him well, I was in absolute nirvana. When my second orgasm hit me it was one of the best ones I had had in recent memory; he did things to my g-spot that practically had me floating off the bed. I thought things couldn't get any better, but then he went for round three.
Dan continued what he had been doing before, much to my pleasure, getting me fairly close to my third orgasm of the night. After a while he asked whether or not I would be ok taking over rubbing my clit from him. I assumed he was asking so he would have a hand free to attend to himself, the poor guy had been neglected the whole time, but boy was I in for a surprise. As I started rubbing myself I felt a finger, quite wet thanks to how turned on I was, slide down and begin to press on my ass. Now, I had never done anything regarding anal up to that point, and actually thought the idea was a tad gross, but in my obscenely aroused state I was way too far gone to even consider trying to stop him.
The tip of his finger slid into my ass without any resistance and, to my surprise, it felt AMAZING. Suddenly the orgasm which had been holding off in the distance started coming on fast and hard; something about being doubly penetrated by his fingers was making things happen like never before. I wish I could properly describe the orgasm that he brought me to, I really do, but nothing I write could do it justice. My back was fully arched and I was making what must frankly have been some pretty unsexy gasping sounds. I don't know how long it lasted, but it felt like I was coming forever, each contraction was long and powerful, pulling my whole body in. I was seeing spots for at least a good minute after he pulled his fingers away, sliding behind me to spoon and cradle me in his arms, our bodies pressed up against each other lulling us to sleep.
Since that night me and Dan have yet to have a chance to repeat that experience (damn the fact that he works nights pretty much every day), but we've both agreed we want to do that again and have been seriously talking about dating. As for forays in to anal, I have to admit I've tried again during my solo sessions, happily with similarly earth shattering results. I don't know if my new-found love is an unusual one (it would be interesting to hear what you guys and gals have to say), but I would certainly have to suggest giving it a try if you haven't already! Anyhow, I'm off to bed, hope everyone enjoyed my little confession.