[m]y first time with my [f]riend | 2016

I had known Carrie since third grade and we had become fast friends. In ninth grade, I started crushing on her hard. However, due to our religious upbringing; nothing could be done about it. After high school, we both ended up far away from each other, her on the east coast while I went to school in the Midwest. We kept in contact through calling and text messages sometimes spending an hour or two on the phone with each other. One day, in the middle of a conversation she asked me, “filling_georges_shoe, do you like me as more than a friend, because I just like you as a friend.” I quickly said “No, I don’t,” as I thought I’d rather have her as a friend than make it confusing and lose her. That seemed to satisfy her and we moved on. However, I did not move on because a crush of five years does not disappear overnight.

Spring break arrived and my boss offered to pay me to drive out to the east coast and pick up some racing equipment for him. I jumped at the opportunity, seeing as I could visit Carrie at the same time. I texted her and she was as excited as I was. After a twelve hour trip, broken up by a short visit with my parents along the way, I arrived. I did not tell my parents about the visit with Carrie, because they would have had all kinds of thoughts that their precious filling_georges_shoe might be getting intimate with a woman out of wedlock. Oh the horror!

When I pulled up outside Carries apartment, her brother and cousin were there to greet me. They chatted about the local goings on while we walked up the rickety stairs to her apartment. We entered the cozy living room and there she was. She was wearing green skinny jeans and a grey tank top. She looked amazing. I greeted her with a “hey Carrie” and she replied back. Of course I had to keep it cool as her brother was right there in the room. After a little smoking session, Carrie and I walked down the stairs and out into the street to go buy some food. We spent a good hour getting caught up. After spending the night on her couch, Carrie and I spent the day driving around and having a grand time. We ended it by getting dinner with one of her girlfriends at a Thai place in the downtown area of the city. Then we drove back to the apartment. This was my last night here and I didn’t know if anything would happen, but I hoped it would. Carrie decided it would be fun to watch some movies in her room and smoke some weed. I was down with that plan so we holed up on her bed and tried to muster something up on Netflix. The weed she had was shitty and we complained voraciously. Her brother stuck his head in and asked for some. Carrie offered it to him and told him it was pretty bad. He then went out and got blazed on the couch, where he stayed for the next couple of hours. I was glad he was out, as I couldn’t see anything progressing with him around.

Soon we were watching archer on Netflix and just chilling together. My smooth little mind deducted that if she wanted to chill on her bed together, maybe she wanted a little more. She had put on some pajamas, and looked very cute. Carrie’s legs are endless and I decided to start there. I put my hand on her ankle and started fiddling with her leg. I slowly moved my hand up her leg until I met her kneecap, where I made some inane comment whether it was her kneecap. I kept creeping my hand up further, and she did nothing about it. She seemed to like it when my hand got up near her pussy because suddenly she wanted to spoon with me. I was down with that, but I was not very experienced with the whole situation. We were awkwardly spooning when she asked me, “filling_georges_shoe, have you ever dry humped someone?” I said “no I haven’t.” I quickly got in-between her legs and started to do what I thought she wanted me to do. I suppose I wasn’t getting things done because Carrie grabbed my hand and said, “Here, filling_georges_shoe, put your hand up my shirt.” I awkwardly was fumbling around when she got impatient. In one fluid motion, she pulled her shirt and bra off and threw them on the ground.

Before me in all their glory were those beautiful boobs I had thought about for many years. Carrie lay back on the pillow, and I just looked at her tan body contrasted against the white sheets, her perfect breasts with perky brown nipples just begging for my attention. I dove into her breasts with my face, sucking on one nipple and then the other. Carrie made contented sounds as I kissed her nipples and her neck. I kissed down her stomach and got to her pajamas. I pulled them down and she kicked her feet until they were off. All that was between me and Carrie’s pussy were some small green panties. She quietly said, “Take them off.” I did not hesitate. I pulled down Carrie’s panties and basked in the first pussy of my life. I went down and without even sticking in a finger, started eating her out. It was a pure carnal reaction, and she tasted good. Carrie was quiet as I continued to lick and peruse her pussy with my tongue, but would later tell me that I had done a very good job.

When I came up for air, we started grinding on one another, but I had yet to ditch my jeans. As my rough jeans ground onto Carrie’s pussy, she wrapped her legs tightly around my body and flinched a few hard times. Then she said, “Get those jeans off.” I, rather shyly, shucked my jeans and underwear off and was naked in front of her. She seemed to approve. She popped up off the pillow and sat on the side of the bed. She grabbed my dick with her hand and started to vigorously jack it off. Her technique was a little trying so I gave her some pointers. After she had jacked me off for a couple of minutes, I gently pushed her down onto the bed and got between her legs once again. I couldn’t take my eyes off her beautiful boobs, and the brown nipples were oh so suckable. My penis was rock hard at this point and we were just rubbing junk together. She whispered, “Filling_georges_shoe, I’ve never been with a boy before.” I said “Carrie, it’s the first time for me too. And by the way I lied when I said I just like you as a friend. I have liked you for a while and you look fucking hot with those two pigtails.” She smiled and said, “I’m not stupid, I knew that all along.”

Carrie jumped off the bed and walked over to the dresser. As she walked over there, I admired her ass. I am primarily an ass man, and it was beautiful. It looked better without the skintight jeans on it. She returned to the bed and rolled the condom down over my dick. I grabbed her and pushed her down onto the bed. I lifted up her legs and tried to enter her, but she was very tight. Then the unthinkable happened. I lost my hard-on. I think it was the nerves. She was a champ though, and didn’t mind just relaxing until it got hard again. She grabbed my dick and jacked it off again until I was hard. The condom had come off, and Carrie said to just go without it. I just had to pull out before I came. Smart thinking there, but I was thinking without my brain.

Slowly, I pushed my way into Carrie’s pussy. It was tight and warm and felt better than anything I could have imagined. I slowly started to fuck her, taking care, as it was Carrie’s first time and she was very tight. She must have lost her hymen through sports or something, because she never had a problem with that. I pulled out too far and my dick flopped down. Carrie reached down with her long fingers and pushed my dick right back into her tight cooch. I still masturbate to that image today. After a little while, I was about to come, so I pulled out and came all over Carrie’s stomach. She lay there, her brown little body covered in cum, and I just drank in the scene. I had just had the night of my dreams, with the girl I had had a crush on for five years, and it was glorious.

I traveled back to the Midwest the next day, and we remain great friends. They say friends shouldn’t fuck, but this worked out very well for Carrie and I. we even had a conversation about what went well that night, and what we both thought the other did well. She later told me she had started seeing a girl, and is pretty much a lesbian now. I am fine with this, but I’ll never be over her. I hope one day we will be more than just friends, but until then, I have this memory.