Well, the post got to 10 likes, and I keep my promises. Plus I’ve already detailed my first blowjob and when I lost my virginity, so I guess this makes sense chronologically.
The first time I ever seriously fooled around with a girl I was 16 years old (she was 17). My friend Kate, who was on the swim team with me, was sleeping over the night. She was one of my best friends and often stayed over on the weekend. We were changing out of our school clothes and into clothes to chill out in. I remember she kind of caught me staring at her breast, which were magnificent. She was about 5’9, so huge compared to me in general. She made a joke when she caught me looking and said “Oh you like my boobs” and kind of grabbed one. We both laughed and went about things normally.
Later that night we were in my bed about to go to sleep and joking around. She was spooning me a little, which was not odd, since we had slept next to each other before. I noticed that this time was a little different, because the was slowly moving her hand around on my stomach. I didn’t say anything and let her do it. Soon she was a little bit closer to me, I could feel her breath on my neck.
Then she said softly “I know you really do like my tits, don’t you?” I said something like “Yeah, I mean I’m jealous.” Then she told me she liked mine too and moved her hand up towards my breasts while slowly kissing my neck. I let out a soft moan, almost accidentally. After a minute or so of kissing my neck, she slowly moved her hand down towards my waistline. I moved so that I was laying slightly flatter, rolling towards her. As her fingers began to slide beneath my shorts, I spread my legs just a little bit to give her indication that I was willing if not begging for her to go further. She eventually got her hand to my pussy, taking seemingly forever.
As her finger first touched my pussy she told me “you’re so wet already.” I kind of giggled but said nothing. She entered me soon after with one finger and it felt incredible. I let her touch me however she wanted, offering no directions. She told me she wanted to make me cum and began touching my clit. Within a minute I was cumming hard. Shortly after, we fell asleep. I was too afraid to say anything and ruin the moment.
The next morning, we just proceeded like everything was normal. I am not sure what I expected, but I thought there’d be some reaction. We hung out a few days later, and again nothing. After a few weeks, I figured it was a one time thing. That all changed while studying for finals, though. We were studying on my bed for a few hours and she said we should take a break. We were lying on our stomachs and out of nowhere she gently put her hand on my lower back. I looked over towards her and she moved in to kiss me. We kissed passionately while she slid her hand down towards my ass. She groped my backside and it made me dripping wet.
We were eventually fondling each other when she abruptly sat up. She took her shirt and bra off and I instantly grabbed her tits. I couldn’t believe how good they felt, they were at least a big C, probably a D cup. I licked her nipples and she began to moan. I was so horny, I wasted no time getting my hand down her pants. She was as wet as I was, and I was surprised by how tight she was. She was a lot tighter than I was.
As I began to finger her, she asked me if I’d eat her out. I said yes, but I was super nervous. She tasted SOOOO good, I couldn’t get enough of it. She also came very easily. I never wanted to stop, but eventually she pulled me up to her. After laying in silence a while, she said she had to go. We hooked up at random like this the rest of the summer before she moved away for college. We saw each other on her breaks after that, but never hooked up after that summer. It didn’t really matter though. I cherish that she was the first.