[M]y [f]irst time with a childhood friend

It started off pretty innocently. I was 20, she was 18. We texted each other like we usually did every once and a while. Occasionally sending selfies or pictures of things around us. We had know each other since I was nine. I had watched her grow from a rough housing tomboy to a beautiful woman, with long red hair, bright blue eyes, pale skin, average sized breasts. I had always had the thought in the back of my mind, of, “what if?”. Well, I sent a pic of my shirt off like I sometimes did. I learned over time that she likes that. She sent a pic back this time. Her jacket was unzipped and you could just see the outline of her boob, covered by the jacket. My heart pounded.

“Move it to the side please…”

I waited for her to respond. What was I saying..I didn’t back peddle though, I wanted to see what she had to say.

“You want to see my bare body??” “Yea, I do, if you want to send it” “Only if you send it too, ill take off what you take off”

I was so nervous. My hands shook, I had never gone farther than kissing with a girl. My dick was flaccid and small because of it. She sent me a picture of her smooth, pale legs. I sent a pic back with just my underwear on. We stripped back and forth, removing more clothes tell we were sending full nudes of each other. She has small but adorable C cups with pink nipples. She is shaven, but not shaved bald, her stomach is flat but realistic to what I have seen with a lot of amateur porn, its not toned but its perfect for me. I was able to calm myself down to get semi hard. After about an hour she watched me cum, my face got flushed as it shot out on my chest. I breathed heavily. I felt like i had ran a hundred miles. My chest was glistening with cum, slowly dripping down my abs. She didnt really comment on it, just asked if I enjoyed it. I said I really enjoyed it, I felt like I was in heaven right now.

I couldn’t sleep that night. I was so fucking horny and wound up thinking about her. I wanted to go over to her place and eat her out. I wanted to do a lot of things to her. But she was in another country at the moment and I would have to wait. A couple days later we talked about it. I wanted to know if we were both looking for the right thing here. If both our goals matched up.

“I want to settle down and find someone, maybe have some kids later and a house” she told me, I let her know, I am not that guy, we can be platonic still. “I know you aren’t, I haven’t found that guy yet” We talked some more about what we both wanted, we both found each other attractive, she trusted me enough that I wouldn’t push the limits on anything and would be the guy to try things with. I asked if she would be willing to be friends with benefits and she agreed to it. We sent some nudes back and forth now that the nervousness was for the most part gone, I asked her if she liked seeing me nude or just shirtless, she said she likes seeing me nude, I sent a few more of those and came again. She asked me how it felt and I told her it feels like a sneeze that warms your whole body and instantly calms you down and makes you sleepy. I asked her how it felt to her, she said she doesn’t masturbate and doesn’t even know how to. I was surprised by this, I told her we should meet up so I can return the favor for her. Due to both of our schedules for work and life, we were both off four days from then.

Even though I was a virgin, since I was 13 I have read so much stuff about sex that mentally visualizing how to do it wasn’t hard. I found several guides to eating a girl out and fingering her. I got some water based lube off amazon just to make things faster. I tried it on myself and ended up cumming in thirty seconds. Yeah, this stuff would work.

When I got to her apartment, she answered the door. She was wearing a long black dress, her hair was let down, she smiled and invited me in. My heart skipped a beat. This is really happening. To preface, I had told her seeing her in some of her dresses made me want to take her to a secluded spot, hike up her dress, and start kissing her legs, up to her panties, feeling the sides of her hips as I licked the fabric, teasing her, by going up to her neck and stomach and her inner thighs. Just to build it up tell I actually go down on her. I have no doubt this is why she was wearing this today. I felt like how I did that night we sent nudes. I could tell she was nervous too, she sat with me on the couch and barely said anything. I leaned in and kissed her. Her lips were soft and warm. She ran her hands threw my hair. I suggested we put on a movie, which ended up being the matrix.

I am skipping a lot of build up here because I feel like its boring to read, but I ended up massaging her back and her legs and shoulders. Running my hands up and down. Feeling her goose bumps rise to my touch. She ended up falling completely asleep. I flipped her on her back. Her legs opened very easily. I took the edge of the front of the dress and hiked it up revealing her pink panties with a little bow on them and frills around the edges. My dick pushed hard against my pants. I whispered to her “you don’t mind if I take my clothes off right?” she shook her head. I took my shirt and pants off, I looked down and could see the precum rising, I might cum before she does. I kissed the inside of her thighs, running my hands up her dress and to her stomach. I hiked it up further, kissing her stomach. I leaned in to kiss her neck, and I could feel my dick on the fabric of her panties. We both were letting out quiet moans, my heart was still slamming. I continued to tease her, licking the fabric of her panties, running my hands up and down her thighs. Finally, I slid my hands up her hips and pulled her panties down. I actually hadn’t seen her pussy before. She could never get a good angle of it in the pictures. She was soaking wet, it didnt smell bad or anything, tasted kinda like sweat. She moaned, a lot. Even though she was wet, I took a little bit of lube and put it on my ring and middle finger and put it inside her. She jumped immediately. I remembered she hadn’t ever masturbated before. I kissed her, I told her to relax, sit back, what ever I do, its because I want you to feel good. I curved my fingers up. She grabbed on my arm, her eyes were dilated and her face was flush. I moved up and down, she gripped my arm harder, I put my hand on her pubic area. “Slow down?” “Y-yeah” she was trying to form words but couldn’t quite make them out. I didn’t stop what I was doing tell she told me to. I felt a muscle push me out, her legs tensed, her stomach tensed. She ended up getting up really fast while still shaking a bit and all the color in her face disappeared and she passed out. I had figured she tensed up her legs and got a head rush. I went to the fridge and got her a glass of water. By the time I filled it half way she was awake and giggling. I handed her the glass, she was still jerking a bit, drinking out of the glass and looking at me smiling. I was stupidly hard. She set the glass on the floor and pounced on me.

“Mine” she said, grabbing my dick. Her head instantly disappeared in her sea of hair as I felt a warm, wet sensation on my cock. I let out a moan, I couldn’t look down, or acknowledge what she was doing. I had to focus on not exploding in her mouth. Her teeth kept dragging passed my head which was the only bad thing about it. I felt her tongue lick around it over and over again, I bit my knuckle and moaned again. I told her I was about to cum. She stopped. I took some deep breaths and held back. I kept my eyes closed. My heart was slamming in my chest again, I was so close to orgasm but I didnt want this to end.

There wasn’t any movement, I sat there with my dick twitching waiting fighting the feeling of cumming. She rubbed my chest. “I’m going to keep going, ok?” “yeah, ok, thats fine”. I felt her get on top of me, and in seconds, I was inside her. A feeling of warmth and wetness enveloped my cock. I could feel her body react to me. She let out a long moan and sat there for a second. My eyes shot open. Her dress was draped over my lower body, obscuring what was happening, but I knew. I felt her breasts, I slid her dress off, I was afraid I was going to get her pregnant, no condoms or anything but I was so horny. I put my arms around her and pounded into her as hard as I could, she let out several loud moans, I wanted to cum inside her so bad. I had a voice inside my head screaming at me, to push myself as deep into her as I can and finish in her.

“I want to cum inside you” “Cum inside me” “I’m going to shoot it as deep into you as I can, I want you to feel me gushing into you” “Do it…”

I felt it building up, I quickly threw her to the side and pulled her dress down. I exploded all over her dress and chest and face. We sat there, breathing heavily. I fell back into the arm of her black fake leather couch. Aside from our breathing, only the ceiling fan above could be heard. She licked some of the cum off herself but I could tell it didnt taste good to her. I went to get her a towel. After I helped her cleaned up. We cuddled for the rest of the night. I was always told that sex would be underwhelming, but I think thats because those people hired a prostitute. I had know this girl my whole life. We had played together in elementary school, and I watched her become who she is today. This was amazing.

Sorry if this was long or there was weird jumps here or there, its still surreal that it happened in my mind. I am just trying to piece together what all happened in that night because it was fast.

Source: reddit.com/r/gonewildstories/comments/8fwxpq/my_first_time_with_a_childhood_friend

2 comments

  1. Great first time memory. I thought you were gonna cum inside her and she wanted you to do it.

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