So I was not particularly cool or popular in school. There was this one girl called Ellen who I quite fancied. She was kind of average height, with curly brown hair and a round face and a slightly bunny looking eyes. She was in my year at school but we didn’t share many classes. The first time I remember really crushing on her was when we went camping as a school group for a week. I remember one afternoon we played rounders in the field and I played really well and she smiled at me after and told her female friend how well I had done in my earshot. The next night a group of us played spin the bottle in a tent whilst it rained outside and Ellen and I landed on a spin together and had to kiss. I had never kissed a girl before so I was stoked especially as she said she was excited to kiss someone clever. The kiss was short and probably terrible but the feeling was nice and the adrenaline rush sustained me for a good while.
Anyways fast forward a few years and I met Ellen at a party. We were both 20. I was a bit tipsy so I mangled telling the above story about rounders at the camp trip to Ellen and her two girl friends she had come to the party with. I didn’t say about the kiss. By this point we had all left school and I was quite a lot more confident and was told I was quite good looking by a few girls. Ellen had become ultra cool, she was seriously pretty and worked as a jazz singer and guitarist. She must have liked my telling the story enough because we talked for most of the party and she gave me her number. Three days later I finally picked up the courage to message and ask her out. She was busy with a gig on the night I suggested but said she could come to my flat the afternoon the day after. I said yes obviously.
Ellen arrived at my flat wearing jeans , a blue and white top and flat shoes. She had bra straps visible and her tits looked terrific. Her bum was poking out nicely from the back of her jeans. We chatted for like twenty minutes before I went in to kiss her. Instantly my mind went back to that night in the tent. We made out for like 10 minutes and I remember her hair smelt really nice. I thought that would be it but she then felt my hard dick with her hands and started rubbing me through my jeans. I said we should maybe get undressed and she laughed a little and then started taking off her top and bra and then opened my jeans. She gave me a quick hand job and I came whilst staring at her naked round tits.
That was basically it for that day and she left after I made her tea. We talked on the phone a few times over the next week and then met up for a proper date on the weekend. We went for lunch in a pub garden that does really nice food. She was wearing a yellow summer dress and blue flat shoes. After the meal we walked in the park and then went to her flat which she shared with two girls and a guy. The guy was in her jazz band. Anyway, Ellen and I made out for ages and I finally told her she had been my first kiss. She sort of smirked and said that was sweet and then we made out and fucked for the rest of the afternoon. The first time I entered her I remember having just a wholesome warm feeling throughout my body. I came inside a condom the first time and went to get cleaned up. Her dress was on the floor when she looked at me on her bed and said she wanted me to stuff her pussy with her special black knickers she had in a draw. I obliged and ate her out for good measure. She was really wet and the sounds she made were like really soft moans that almost sounded like hiccups. Her sex hair was divine and after a bit she orgasmed (or at least she said she did). Then she got redressed into the dress , put on some of her own jazz music on her vinyl player and stripped whilst dancing and singing. The song didn’t really suit stripping but I wasn’t about to complain. We fucked again and then I asked if I could put it in her bum. To my surprise she said yes and I pounded that cool girls bum hole over and over. Hard. I came insider her hole and we made out again. She got cleaned up an said she wanted to be occasional fuck buddies and nothing romantic. I said yes and she gave me the black knickers to take home.
Source: reddit.com/r/gonewildstories/comments/kn12bj/anal_and_panty_stuffing_with_my_school_crushfirst