Losing It

I've always been a fairly shy guy and I recently had an experience I'd like to share. I've been told I'm good looking, but I've never had any success with women. I went through high school without losing my virginity, and it's always been in the back of my mind that I was a loser because I couldn't get laid. I'm nineteen now and last night I had sex with a girl for the first time. It was a lot different than I expected, and the chick I did it with was wilder than I'd ever imagined.

I used an online dating site to get a date. I think I actually had a harder time than most guys because I'm honest. No one seemed to believe I was a virgin, but the first woman to listen was a 21-year-old college girl (I'll call her Penny here to keep her real name anonymous), and she found it exciting- enough to want to meet in person for a weekend date.

I rented a cabin in a country and arranged to meet her there. She said she had a boyfriend, but he was busy that weekend with some fraternity stuff and it would be easy for her to slip away. Somehow knowing she had a boyfriend made her an even better catch.

I got to the cabin first and waited for her to show up. I told myself that it didn't matter if she didn't show- I needed the vacation and it was worth risking the cost of one night's rental on the chance that this could change my life forever. It was off-season, so it wasn't that much anyway.

She showed, and I was so excited and nervous I must have seemed like a total idiot. I could barely string two words together- I was actually stuttering. She was a brunette and in very good shape, exactly the type of girl I never in my wildest dreams I ever thought I had a chance with- and that really didn't help my nerves. As she walked through the door my eyes were glued to her body and my cock uncontrollably became rock hard when she started flirting with me. It was very embarrassing, especially since she noticed and commented that she thought I was excited enough to be a virgin. Online we'd talked about my virginity quite a bit, she was still skeptical, but said she was willing to find out for herself.

I helped her with her bags and offered to make her something to eat on the stove and when I turned away for a second she removed her shirt. As I turned around I just froze, staring at her perfect bare breasts. "I already ate," she said casually, and then stepped out of her pants and came towards me. I really didn't know what to do as she put her arms around me.

It was like I was dreaming, and I was so shocked I didn't even kiss her back when her tongue darted into my mouth and around me lips. She actually said she liked that, but at the time I didn't even know what she was talking about. My hands naturally gravitated towards her breasts though and her nipples were rock hard beneath my palms, a very different sensation than I'd imagined. I never knew nipples could get that hard!

She pushed her right nipple into my mouth and I sucked on it instinctively. Her body felt incredibly warm and she smelled so nice all I wanted to do was lick her everywhere. Eventually I worked out a plan and decided we needed to get out of the kitchen. I walked with her in my arms upstairs to the bedroom, the whole time alternating my mouth on her nipples and her neck. She seemed to really enjoy everything I did with my hands and tongue.

In the bedroom I put her down on her back and she shoved my head between her legs. I lapped at her pussy and she instructed me to lick and suck the top of her clit. My tongue was sore by the time she had an orgasm, but she thanked me over and over for not stopping. By this time I was so turned on I'd soaked my underwear with pre-come. When she helped me out of my clothes it was like my entire body had goose bumps and when I felt her warm mouth close around the head of my cock it felt so good I thought I would die.

Unfortunately she bobbed her head up and down on my cock and I came in her mouth after only a few seconds. I came so fast it even surprised me. What she didn't get in her mouth went in her hair and on her face. She spat on the floor and I apologized, but she seemed upset that I didn't warn her I was going to come. I'm pretty sure she finally believed I was a virgin at that point.

I worried she was going to go home after that because she ran out of the room and downstairs to her luggage. I was too out of it to do anything though. I'd just had the best orgasm of my life and I laid there on the bed dumbstruck and cursing myself for not knowing what to do. As it turns out she went to get her toothbrush and returned still naked and brushing her teeth. She smiled at me and went into the bathroom to rinse and clean up. I followed her, now completely naked and hard again.

After she spit the toothpaste out we played around a bit, cleaning my come out of her hair and then she bent over the bathtub and told me to fuck her from behind. As I got in position she spread her ass cheeks apart giving me a perfect view of her pussy. As I slipped my cock inside her she shuddered with what I thought was another orgasm, but it might have been something else. Doing a girl from behind like that wasn't how I'd imagined my first fuck, but it was incredible. Her pussy was hot and velvety soft and I could feel the muscles of it contract around my shaft. The only benefit of coming so fast in her mouth was that at least I had a bit of staying power (or so I thought). I still didn't last all that long while fucking her, but we got the chance to do it in a couple of other positions before I came on her tits.

She said she believed I was a virgin- no guy she'd ever known had come so fast twice in a row. She then got a wicked look in her eye and told me to wait while she went downstairs again. She returned with a bottle of lubricant and said she was going to rock my world. Without saying anything else she got down on her knees and poured some of the lubricant around her asshole and fingered her anus in front of me. She then took my hand and helped me put my index finger in her butt.

I never thought that anything could be so hot and tight. It was weird, but it was the most erotic moment of my life. She moaned as I anal probed her and I could feel her ass loosening up around my finger. She had me stop a couple of times to add lubricant and after a few minutes of this I was totally hard again. I couldn't believe it turned me on, I thought I'd be grossed out. She reached around and when she discovered I was hard she told me to cover my cock with lube and put it in her ass.

I did as I was told, only when I placed the head of my cock against her rosebud she told me to wait and reached back to grab the base of my cock. She did everything from there, easing her butt down very slowly. Fuck, I thought it felt tight to have my finger up there, I didn't think it would ever fit! I never actually found out though, it was so tight I didn't make it all the way in before I came. Her sphincter just made it over the tip of my cock and I unloaded for a third time. After that I was completely spent and I stumbled to the bed and fall asleep. When I woke up she was gone. She didn't stay for the weekend, but since I'd scored, I really can't complain.

She hasn't returned any of my emails so I have to assume she didn't think I was a very good lover, or possibly didn't want to cheat on her boyfriend again. I'm still not going to give up on her, but I'm not going to stop trying to find other women online. Stick to what works I always say. I feel a little disappointed that I wasn't able to completely satisfy her, but I'm very relieved I finally lost my virginity. I feel like a man for the first time in my life and I owe it all to Penny. I'll never forget her.

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