This is a little bit late but in the same week as New Years so fuck it. This is also when I was pretty new at sex so awkward warning but we were still both older than 18 at the time. Look for the —— break to skip to the good stuff
I had been going to school on the east coast for about 9 months already and a friend, Maddie, and I were messaging back and forth on Snapchat. Nothing too risque, she and I would talk about whatever. Eventually coming up on Christmas and New Years she started getting really excited about my plans on coming home for the holidays. We had made some vague plans to see each other.
To give a description of Maddie; she was about 5’4″ with long brown hair. She was a little bit chubby but had a well developed pair of boobs, probably in the High C low D range. She also had a gorgeous set of light brown eyes.
Well time had come for the holiday break and I bored my flights and went home. My mind packed with possibilities of what could happen, impatiently waiting on multi hour long flights to take me back to the Midwest.
By that Friday our friend group decided to go see the movie in the Hobbit series. Side note: I might be a nerd but this was totally Maddie’s pick, not disrespecting Tolken but I hadn’t seen any of the other movies in this series and she is a hard core LOTR fangirl. We sat through the movie with nothing happening considering Maddie’s eyes were glued to the screen and God could not help you if you interrupted her during that movie.
After the movie the we were on our way back to someone’s house and awkward, nervous me was trying to figure out what move to make. At whatever point I had finally worked my nerve up and took the initiative. THAT IS WHEN I BOLDLY… reached out and held her hand. Yeah kind of a low level entry move, but I felt her fingers curl around my hand too. It wasn’t until we got back that our friends in the front seat turned around and saw us and that is when our friend Jen freaked the fuck out.
“OH MY GOD IT’S FINALLY HAPPENING!” she exclaimed. My buddy Jack then proceeded to pull a Jason Borne and got her out of the car so fast I truly don’t know how he did it. But as soon as they cleared the car, I reached over and placed a hand on Maddie’s cheek and pull her closer and began making out with her. When we broke free she blushed hard and gave me a “wow”.
“You don’t know how ready I was for that.” We made out a little bit more and went inside. The night ended without much further incident but Jack gave me an attaboy in private and Jen proceeded to ask too many questions and generally gush over the fact we made out.
The next few days were spent being dumb on Snapchat together. We wouldn’t see each other again until New Years Eve. Which was at Jack’s parent’s house. It was just the fours of us from before celebrating the New Years. Maddie and I made out a lot that night and consumed many alcohols. Long story short there is we played games and watched YouTube videos, but eventually we had to end the night.
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We stood in the kitchen and Jack asked the pivotal question of the night. “Alright, Maddie, Who do you want to sleep with?” Maddie simply grabbed my hand and ran up stairs to the awaiting guest room. We were in such a rush we didn’t turn the lights on.
We started making out on the bet and I pulled off her pants, she started unbuttoning my shirt. I kissed her neck and she let out a moan. She responded in turn by biting my neck and the sensation was unbelievable but I was concerned about having to explain hickeys in the morning to my parents so I asked her to stop.
I pulled off sweater and bra and started kissing and sucking her nipples while she rubbed my hardened dick through my pants. She began pulling them off and pulling at my underwear when she stopped and asked “Do you have a condom?” I replied yes and got it out of my bag and rolled it on. This action usually causes me to lose a little steam, to be fair is there really anything sexy about putting on a condom? We went back to making out and I recovered rather quickly.
I layed out on the bed ready for Maddie to mount me. She took me in her mouth for a little bit to make sure my dick was nice and lubricated for her and she slipped me inside her pussy with a moan that sounded a little painful. “Are you ok?”
“Yeah just a little bit bigger than what I’m used to”
Now a days I look back on that as a compliment but at the time I had only not been a virgin for about six months and the previous girl had never made a sound like that so my automatic response was “Am I… in your ass?”
“No. Keep going I’ll be fine.” I started pumping, listening carefully to her breathing as I thrust into her. I kept building speed and she started moaning. At some point she asked to change position and rolled onto her back.
I reentered her and kept speed. Her moans grew louder then I felt her shudder and her pussy grew tight on my dick. An orgasm racked her body. I continued until she told me to stop and she had me lay down.
She removed the condom and began sucking me. I was enjoying the blowjob when a thought crossed my mind. “Swing your ass up here”
“Why don’t I trust you?”
“I just want to 69” It was then that she complied. I started eating her pussy when I felt something hard against my tongue. It was her clit, and then I started licking and sucking it. I heard her moan and shudder as I gave her clit attention. But it was at this point I was getting close and she could feel it. She went harder and deeper on my dick with her mouth until I eventually couldn’t hold back and longer. I came in her mouth. She went to the bathroom and got cleaned up.
We cuddled the rest of the night and went our separate ways in the morning we would see each other one more time before I went back to go skiing.
Unfortunately the rest of story doesn’t involve sex and gets a quite a bit too heavy for this subreddit, but I feel it’s always great to remember the good times.
Source: reddit.com/r/gonewildstories/comments/ekc166/my_new_years_eve_fuck_with_a_friend
Your friends truely a hero