Where it happened: School Auditorium
Langauge: English
Sex: Male
Rating: 5
Category: Straight
This girl Kathy was in elementary school with me, and I worshiped her from afar. I even secretly pasted her picture in my picture book page for “My Sweetheart”. (The school photos always included wallets to trade and a booklet with pages labeled “Best Friend”, “Favorites”, etc.)
In high school I did lighting and sound for the school play. Kathy painted sets. I was very shy, but I always forced myself to say “Hello” to her. Later I started adding “What’s happening?” and after a few days, we were actually talking. A miracle for me!
So one after afternoon Kathy was painting a mural on the scenery, and everyone finally left. She stayed because her picture was an original and she was its only artist. I offered to paint trim, and she had me fill in the sky and some other background before she painted clouds and plants on top of my work. Except, when I’d finished, my base paint wasn’t dry enough for her to paint over without smearing.
I was shocked when she asked me if I still had a crush on her, and started telling me about how I always got a picture of her from 3rd grade on, and tried to set close to her in Junior High. Apparently I didn’t know how to keep my infatuation really secret! Kathy told me that my shyness made me (ugh!) cute, she liked how smart I was, and how she really enjoyed talking to me.
Then she covered her paints and brushes, stood up and said, “Come here.” Taking me by the hand, she led me off stage to where she kept her purse, and then into the side room we used as a ‘green’ room. She put me on the couch and sat down right next to me, and put her arms around me. “I have a really good way to pass the time while the paint dries. Cuddle up with me and let’s get as close to each other as we can.”
Kathy started petting me, and when the shock wore off, I returned her caresses. In a while, she unbuttoned her smock and moved my hand to her boobs. She only had on a bra, no shirt! Eventually, I found panties were the only other thing under her smock!
When I got my hand to her snatch, it was oozing slickness and my finger slid down right between her inner lips. I didn’t know what to do next, but I figured if fucking was sliding your dick in and out, then I should do the same with my finger. Each time I stroked, I was running my finger over her clit, and it didn’t take too many passes before Kathy moaned and started shaking with an orgasm. (Back then I didn’t know what I was doing, but now that I’m experienced I understand what happened.)
Finally she grabbed my hand to make me stop. “My clit’s too sensitive; it needs to rest a bit. And you need to get off too. I’m really afraid of getting pregnant, but there is something which we can do that you’ll really like.
“My mom told me that she can also orgasm from the back as well as the front, and said I’d probably be the same way. She warned me to use lots of lube and stretch myself open and make the guy hold still when I first slid his dick inside me.”
Kathy got out a condom and a squeeze bottle of some very slippery stuff. She rolled on her side and lifted her knees up to he chest presenting her bottom toward me. “Put some lube on your finger, and rub around my anal ring. And stay out of my pussy, or I may get an infection.”. I circled around the ring, and then she told me to “put on some more lube and pull from the center out like you are snapping your finger.” Each time I tugged on her anal ring, my finger started in deeper and she got looser.
“Get some more lube and push your finger all the way in. When I’m loose enough, put more lube on and try two fingers.” Finger banging her ass hole was neat, and I slathered lube around as I worked to get two fingers all the way inside her. She lifted a leg and rubbed her pussy. “That feels good. Keep going slow and easy”
“OK, I’m ready now. Put on the condom while I get on my hands and knees”. Thankfully, sex education had taught me how to use one. I stood up and put it on, and then put some lube on it. Kathy reach behind her and pulled her butt cheeks apart, and I knelt on the couch and lined up with her back door. She started sliding backwards onto my shaft and I moved my hands to her hips. When I’d sunk all the way down, she said “Go slow at first” and let go of her cheeks.
I started moving, and it was the sweetest feeling I’d ever had. My cock was totally in her clutch from tip to base. Some of my best cums have been from anal, and I owe it all to Kathy for showing me the right way to make it good for my partner. She opened up many back doors to me beside her own!”
As soon as I started sliding in and out, Kathy started moaning. She let herself down until she was lying flat on her tummy with her hand between her legs. “Push down towards my pussy” she gasped.
I put my legs on the outsides of her hips and shifted forward to stab almost straight down against her public bone. I heard, “My god, oh my god!” and then Kathy started quaking. It was less than a minute since I’d put the head of my cock on the bull’s eye, and I already knew I couldn’t stop my impending eruption.
After I filled the condom, I slowed down. Her order to “Don’t stop, don’t stop until I say so!” got me moving again, and her tightness was quick to get my erection back to full strength. “Cum again as soon as you can. Don’t hold back!” I was afraid the condom would come off as I sped up to pound against her butt cheeks. Surprisingly, I was soon ready to cum again!
“Damn, Kathy, you feel so good! Oh I love you! And I’m ready to cum again.” I felt my cock swell so tight I thought it might burst, and then I gushed forth again. “Yes, yes, I’m cumming! Oh this is such a good cum, this is wonderful cum.” My balls itched and I felt like I’d tried to turn myself inside out. I held myself as deep inside her ass as I could go. “Oh thank you, Kathy, thank you, thank you, thank you! This is the best cum I’ve ever had. You’re so good to me, Kathy, you are so wonderful!”
“Stay inside me, Mike, I want to feel the fullness as long as I can.” I lay on top of her, probably putting most of my weight on her, until I finally shriveled and popped out. I could have just gone to sleep but I made myself kiss Kathy’s neck and shoulders instead. When I got up, the condom slid off trapped between her legs. I picked it up, trying not to spill, and wondered where I could dispose of it without getting anyone in trouble.
Kathy got up, and got a couple of towelettes from her purse. After I wiped off and got my pants on, I wrapped everything up and put it in the plastic bag she produced, and the bag in my back pocket until I could pass the dumpster. Kathy was prepared for everything but the big wet spot we left on the cushion!
I stayed with her until she finished the mural, and we made plans for a date. The rest of the year was lots of fun together before we left for different colleges. When her mom saw she had a steady boy friend, she got Kathy on the pill. Then at certain times of the month, Kathy would let me put on a condom and fuck her pussy. I’m not sure which way I liked best!
Processing your request, Please wait....
