Where it happened: Her house, living room couch
Langauge: English
Sex: Male
Rating: 5
Category: Straight
This is my recount of my first time. I swear to God it’s storybook quality.
You see, my friend Maddy and I had always been close, and she was into everything I was. Doctor Who, Bleach, Star Trek, you name it. We were a very nerdy pair. Obviously, as boys do, I grew up and began to notice girls, and Maddy noticed boys. Maddy was the pudgy type, blonde with glasses, and I was gaunt like a scarecrow. We never did anything with each other, though we did admit to taking matters into our own hands after a botched date.
So, we made a plan to tell each other which of the guys or girls would be most likely to date us, and Maddy would tell me which of the girls were more likely to ‘put out’.
Well, I dated many of them but I always chased them away. I’d always screw up somehow, and then feel even worse when Maddy struck out as well. No one liked us, and neither of us got past third base. Then came that fateful day.
I was on a date with Georgia, and we were getting along really well. It was the third date, and I had invited her back to my place. We had started to get rather heated, touching her chest and licking each others to view when I got the bright idea to try and reach under her skirt. She slapped my hand away, called me a pervert and left. What? Ugh.
So, as I do I walked the few streets it would take to get to Maddy’s house. She had a date the same night, you see. Third date as well. We had hoped to have that planned out so we could then tell each other about our first times the next day. Well, we agreed that knocking isn’t strictly necessary when entering each other’s houses, so I just opened the door and walked in, expecting to either find the house empty, Maddy on her lonesome or Maddy and her date.
The second option was right. I did find Maddy on her couch, alone, one hand under her shirt and the other between her legs, panting and moaning. Apparently, her date hadn’t gone so well and she decided to take matters into her own hands. I was…well, transfixed. What boy wouldn’t be?
I must have been there for a while, because eventually she gave a soft cry of ‘Jesus!’ and presumably came, bucking and writhing madly. When she was done, I then chose that precise moment to sneeze and catch her attention. That went about as well as you could have hoped. There was yelling and shouting and covering up.
She calmed down after a while, and I sat next to her and asked about her date. Poor girl was outright rejected, the guy didn’t even show up. She had begun to cry recalling it, a big contrast to what I had walked in on not 20 minutes earlier. I threw my hand around her shoulder to comfort her…and the next thing I knew, she kissed me. Full on.
We had never even considered each other, idiots that we were. We both silently agreed that we would be each others first. I still don’t get how Maddy went from outrage, to crying, to super-horny in about half an hour. Anyway, I undressed her slowly until she was completely naked. I removed my clothing as well, and as we both stood starlets, we began giggling like small children at each other.
After the laughter subsided, there was kissing, sucking of nipples (accompanied by further giggling) fingering and my giving her oral (lots of moaning and pleading there) She told me to stop before she came though. She then lay down on the couch proper, and I lay atop her. I then quickly got off of her and put on a condom, red-faced.
We had a plan; I would get her to cum, and while she came I would pop her cherry. Genius.
When I entered her…bliss. Words cannot do it justice. Warm, tight, wet…It didn’t last long, about 2 minutes. Maddy came, I broke her cherry at the same time, and then we missed as I shot into her.
Well, after that Maddy and I began to date each other. It worked, or rather works. Still dating her today, the laughs are legendary, the good times roll and the sex is varied and hot. We’ve covered quite a bit: oral, hands, toys and more recently anal. I thought the front was tight…
But nothing we do could ever compare to that first time with my best friend and my greatest love, Maddy.
What’d I tell you? Storybook worthy.
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