I went through high school without losing my virginity and I always thought I was a loser because I couldn't get laid. I'm eighteen now and still a virgin. I have a steady girlfriend, but she wants to wait until were married to have sex. Ive tried everything to get in her pants, but eventually I just couldnt wait and I decided to use an online dating service to meet someone for a one night stand.
It was hard to do, but I think it would have been easier if I hadnt been so honest. No one believed I was a virgin, but one woman did listen long enough for me to score. She was a 30-year-old redhead I'll call Allison to keep her real name anonymous. I was a bit surprised to find out she was married, but I didnt care.
She said she was only able to get away from her husband for one weekend and she wanted to meet somewhere very private. I work at a lodge in the country and I told her I could swing a free cabin rental. The timing was perfect because the season doesnt really start for a few weeks and I knew wed pretty much have the place to ourselves. It wasnt even something I could get fired for. My boss lets us bring friends out every now and then as long as we clean up afterwards. Allison went for it in a big way and I dont think Ive ever been so excited about anything.
I lied to my girlfriend that I had to work and it bothered me, but I forgot all about being guilty when I met Allison face to face. She wasnt anything like Id imagined, although I think I let my imagination run a little wild. I dont know how to say this, but I sort of thought shed be very demanding, or have a kind of mean streak (she was after all cheating on her husband), but in person she was very friendly and she had a great sense of humor. I also thought our age difference would be obvious, but she appeared and acted like any girl my age. We got along like wed been friends forever.
As expected, the resort was pretty much empty. After helping her with her bags I gave her a full tour, which included a walk along the lakeshore. I didnt plan to have sex with her right on the beach, but thats exactly what happened. I made the first move to kiss her, but after we necked for about a minute she pulled my shirt off and put her hand down my pants.
I was already rock hard and from there she helped me out of all my clothes and got down on her knees in front of me. She said my cock was beautiful and then put the head in her mouth. Oh my god was all I could say. Her mouth was super hot and her tongue flicked the underside of my shaft as she started bobbing her head up and down, taking me deeper with each stroke. Eventually she had the whole thing in her mouth and I dont even know where it went.
It was the most fantastic feeling in the world. I almost came right in her mouth but my knees buckled uncontrollably and I fell down on the sand, pulling her on top of me by her shoulders. It wasnt graceful and she laughed and told me she finally believed I was a virgin. I was very embarrassed, but I saved the moment by kissing her and helping her out of her dress.
Her breasts were perfect. They were just big enough for my hands. With her encouragement and instruction I fondled and licked every inch of her body. I couldnt get enough of her and we ended up in a sixty nine. I lapped at her pussy like crazy while she deep throated me again, and this time I really did come in her mouth. I couldnt help myself. She swallowed it all and then rode my face until she came, her whole body shaking in spasms.
It was just enough time for me to recuperate and she looked deep into my eyes while lowering her hole down on my cock. With one motion my virginity was gone and I savored every inch. It really felt different than Id imagined. It was better than my wildest wet dreams.
We fucked for a long time, and in many positions, but I think I liked it best when she was on top. I did everything she asked, which included rubbing her asshole with my finger and coming in her mouth a second time. She was definitely a kinky sex teacher.
When we got back to the cabin we didnt have the energy to do anything but sleep. My cock was really sore, even the next day, but it didnt stop me from continuing my sexual education. We fucked non stop the rest of the weekend and I swear it was all just as good as my first time. We did some seriously kinky stuff too. I even fucked her in the ass, which turned out to be a lot less gross than Id ever imagined. I actually loved it.
When Allison and I said goodbye it was with an understanding that this was a one time only deal. I definitely want to see her again, but I probably wont. When I saw my girlfriend I thought shed somehow know what Id been up to, but she didnt have a clue. Ive thought a lot about breaking up with her, but I cant make up my mind. All I really know is I think I lost my virginity in the best possible way. I have no regrets.
