Anal on the First Date
I met Logan on Tinder, and he drove his van/house to a campsite just outside of my town so that we could meet up. I went there right after work, and we shared a couple cups of whiskey hot chocolate while we got to know each other. There wasn’t much whiskey in it- to be honest I never really got a buzz off of it, but it helped to break the ice. He had long hair and a runner’s bod (a bit skinnier than what I usually go for), and was wearing flannel pajama pants. Kind of a dirty hippie type, but seemed to have good hygiene, so I went for it. When we finished our drinks, he started kissing me. He went right for my bra, and unclasped it with one hand like a champ. He played with my nipples under my shirt as we kissed, and within a couple minutes we had transitioned to his bed. As he laid back on the bed I pulled off his pants to find that he had no underwear on, and his (more than adequate) already hard dick popped out. I undressed myself and crawled up to him. Space was a bit of a challenge in his van, since there was only about three or four feet of space between his bed and the roof. I laid on top of him and we kissed and touched each other as I stroked him. I continued to stroke him, letting my kisses gradually drift South until I was close enough to take him into my mouth. I won’t reveal all my secret head tricks, but after about five minutes or so he told me he was coming, so I sucked even harder and gulped it all down. When I finished cleaning him up I crawled up to him and he kissed me deeply. Then it was his turn, and he went straight to work on my wet cunt. He started with the clit, taking it into his mouth and sucking on it. He stared up at me as he dove harder into my pussy, and I grabbed and pulled at his long hair. He was doing a pretty good job, alternating between quick strokes of his tongue against my clit, licking around my hole, and sticking his tongue as far as he could into it, until I was just begging him to be inside me.
He grabbed a condom, and slid into my pussy so effortlessly. Because of the low ceiling on the van, I had my legs up with my feet pushing against the roof, and the way he was driving into me in that position hit my G-spot perfectly. I knew I was going to be squirting a lot tonight. Every few thrusts, he would push himself as far as he could inside me and grind himself there while kissing me passionately. Then he would pull himself almost all the way out and then start pounding me hard and fast again. It was a unique technique, and I have since tried to replicate it with others, but I’ve never been able to have that same feeling again. However he was doing what he was doing, it was fucking working. Whenever he would go deep and grind inside me, I would grab his ass and try to pull him even deeper. It felt so good to have him moving slow and rhythmically while he was deep inside me like that, and I wanted all of him. At that point he told me he wanted my ass, and with as good of a job as he had been doing at everything else, I figured I should probably let him have a crack at it.
He flipped me over, and because of the limited space, I had to lie flat on my stomach, ass down. I was so tight that I had to help guide him in. He began again with the same technique as before- pounding me hard at first, and then pausing inside me, going deep and grinding slow. He kissed the back of my neck and shoulders as he rocked me from behind. Every time he pushed himself deep for the grind, I had such a wave of pleasure that I almost felt dizzy. On his last grind I squirted all over the place, which sent him over the edge, blowing his load inside me. We got up and cleaned ourselves up a bit, and I prepared to go. He told me I should stay- that round two would be even better, and I didn’t need much convincing. We crawled back onto his bed and he wrapped his arms around me and pulled me in close for a kiss.
One kiss turned into a few, and he slid his fingers down to lightly tickle my clit. He kissed me deep as he swirled his fingers around it, absorbing my little moans into his mouth. He persisted in this for a long time, slowly building me up. I came again, and breathed a deep sigh of relaxation, after which I kissed him and went back down to see my new best friend. It was rock hard already, and I looked up at him with big doe-eyes as I slapped his cock across my face and tongue, and flicked the tip and underside of his head with the tip of my tongue. He was shaking, and stared me in the eye as I started sucking. After I got him warmed up, he asked me to climb on top (an admittedly challenging feat in the space we were in). I slid him inside me, and bounced and grinded my hips on him as he thrust his hips toward me. Because of the low ceiling, we were face to face the whole time, so we kissed and sucked on each other’s tongues as he gasped and moaned when I grinded on him. My tits were bouncing everywhere, and he alternated playing with them as they brushed his face, and holding my ass up to help me bounce on him. I wanted him in my ass again, so I slid him out of one hole and into the other without skipping a beat, and continued bouncing. Every grind was like fireworks. Just before I was about to cum again, he said he wanted me doggy style.
So we got off the bed, and he bent me over a cooler and rammed himself into me. At this point I was getting pretty sore (we hadn’t lubed up intermittently), but I didn’t care. I never wanted him to stop. He fucked me that way for a good 15 minutes, pulling my hair and slapping my ass as he drove hard into me. Finally I came with a huge, final squirt, and a scream that echoed through the forest outside. He kept going for a few minutes after I came, determined to get a third O for himself as well. He pulled himself close to my ear and whispered to me as he ground himself deep that he wanted me to suck him dry. He pulled back and I turned quickly around to push him onto his bed. I knelt on the floor in front of him, and proceeded to give the second messiest blowjob that I have ever given. I was dripping with saliva all over the place, and forcing his 8 thick inches all the way down my throat, holding back my gags and gasping for air each time I retreated. A couple minutes of that and he was ready to burst. He let out a load moan and yelled, “can I cum baby?”. I just nodded with his cock still in the back of my throat, and I felt him convulse as his warmth dripped down inside me. I pulled him out and made a show of licking the rest of it from the tip of his head, and staring him in the eye as I licked up some of the drippings from my chin, chest, and fingers.
We both fell back onto his bed, and he wrapped me in his arms. We chatted for a bit, touching each other lightly and laughing as we shared horror stories of other internet dates that had gone wrong. After a few minutes, I got up and got dressed to go. I hopped out of the van, and he kissed me and said that if he got to see me again, he would consider himself lucky. I thanked him, but told him “Don’t count on it”, and walked away very satisfied and feeling like a bad ass bitch. He texted me the next day to tell me that he would rate our encounter an 11/10, but I believe in using the scale accurately, so I’d say 10/10. I desperately wanted to fuck him again, but this was pretty early in my open relationship so I didn’t think I was ready for meeting up with someone more than once, especially if I wanted to so bad. So Logan moved off to the next town, and I was left to fantasize about that night for many subsequent months. Ladies, if a van named Caroline happens by your city someday, don’t hesitate to hop in!