This is a story from my senior year of high school, everyone in this story is 18. I don’t remember all the dialogue exactly, but I’ve written it as accurately as I can remember. Also my first time writing one of these, so advice is welcome.
Back then I was part of a friend group that hung out semi-frequently. In that group was a girl we’ll call Summer. I had never been super close to Summer as we were more friends-of-friends, but we always got along pretty well. She was sweet and friendly and just had an electric personality. It helped that I found her extremely hot too.
Summer had shoulder-length auburn hair with bright blue eyes and a dusting of freckles across her cheeks. She also had a great body from years of softball, standing at maybe 5 foot 6 with round breasts and a toned stomach. She turned heads frequently, and she knew it.
As for me, I had medium-length brown hair with green eyes. I stood maybe a little taller than summer and was never the most athletic person in the room, but years of exercise on my own left me with a fairly capable physique.
At the time, Summer’s infectious laugh and teasing sense of humor were leading me to think about her more and more. You could probably call it a crush, though I was never serious about it as I thought she was completely out of my league. There were always a crowd of boys chasing after her, some much more popular than me, yet somehow she never seemed to settle with a boyfriend.
This one particular night, Summer, I, and maybe 4-5 other friends were hanging out at her house. This was pretty common for us, as her house was the most central and her room also happened to be pretty isolated from where her parents usually hung out. That night, we were sitting around watching TV and chatting about who knows what when one of our friends announced that he’d gotten a text about a party happening a few blocks from there. After some discussion, the rest of the group elected to head over to that party while Summer and I stayed put. We had our own separate reasons for disliking the party’s hosts (long story). Plus I wasn’t exactly against spending some alone time with her. Once the group left and the door was shut, Summer started the next episode of Game of Thrones and sat next to me on the bed against the headboard. She was wearing a v-neck crop top and shorts to deal with the late-spring heat, a fact which I secretly appreciated, but before long she crossed her arms and curled up.
“Ugh I’m cold, a cold front must have just come through or something.”
“Yeah maybe,” I said before pausing, weighing the risk of my next move. “Here.”
I put my arm around Summer’s shoulders and pulled her into me as I felt her body relax into mine. Her hands uncrossed and one laid across my stomach, sending a jolt of electricity up my body. “Thanks”
We sat like that for a while, almost cuddling while we watched the TV. My hand felt the soft skin of her arm and her breathing pushed into my chest as I took in the smell of her perfume. It felt amazing, so safe and secure even though I was the one holding her. If you can’t tell, I was a little starved for female attention at this point.
A little bit later, Summer readjusted to turn and tuck herself into me, placing one leg over mine. She moved my arm from resting her around her shoulder so that it now bent around her neck. At that position, my hand hung down so that it just grazed the top of her breast over the shirt but Summer didn’t bother to move. Thoughts raced through my mind as to what it might mean, but I pushed them aside and chalked it up to her being comfortable with me. At that point we were definitely cuddling and I just hoped that she wouldn’t move her leg to feel the erection slowly building in my shorts.
After a while, I discovered that my vantage point allowed me to see a bit more of her cleavage down Summer’s shirt. Inevitably, I ended up stealing glances from time to time. I felt a little guilty, but it’s like I was transfixed. She would take a breath and her boobs stretched outwards against her shirt so I could see the skin curve down almost to the nipple. I guess she didn’t wear a bra for the heat either.
I tried to make my looks short, but before long one of my glances was interrupted by Summer’s finger pulling my chin upwards to look into her eyes as she smirked.
“S-sorry.”
“No it’s fine,” she giggled. “I’m sure you’ve seen much more of a boob than that.”
“Actually no,” I said before letting out my own little embarrassed chuckle. “Never got the chance.” Not in person anyway. We were watching Game of Thrones after all.
Summer gasped, half incredulous and half amused as she placed her hand on my chest. “You’re joking.”
“Nope.”
“Seriously? Wait, have you even kissed a girl?”
“Yeah, in 7th grade,” I said. “But that went about as far as any 7th grade relationship goes.” Somehow I had terrible luck with girls as a teenager, which was part of why I assumed Summer was out of my league.
“Wait, so you’ve never seen boobs in person?”
“Yeah, I can’t say I have. It’s a tragedy.”
The room suddenly got quiet as whatever episode was on ended. Summer paused a moment before leaning in.
“Would you like to?” she whispered.
Now it was my turn to be in disbelief. “Wait… really?” I whispered back.
Our faces were inches away by this point as I stared into her stunning blue gaze. I could even feel her warm breath on my lips as our hands tentatively hovered over where they had been resting. I was suddenly aware of the sexual tension which had been building for the past hour.
“I think you would.”
She ran her fingers down my chest as the sensation enveloped me. I barely had time to squeak out a “Yeah” before her lips met mine in a deep kiss. I wavered only a moment before returning the kiss as my lips sucked on hers, her taste driving me crazy. Her lips sucked and pulled on mine almost desperately. Soon she pulled her leg all the way over and got on top of me as her tongue started thrusting into my mouth, our bodies pushing against each other and our hands caressing each other’s face and hair. I have no clue how long we made out like that for, it could have been anywhere from 5 minutes to 30.
Eventually, I got bolder and slowly moved my hand down her neck and chest before grabbing her hanging breast through her shirt. Her moan into my mouth gave me all the courage I needed to fondle her boobs further. They didn’t feel like I expected. They were firmer yet softer than I had imagined, and my hands wasted no energy in exploring then over the thin layer of fabric as we continued to French kiss. I loved the feeling of her moans stifled my my lips and I quickly learned how to touch her in the most sensitive ways. Her hips slowly started to buck ever so slightly against me and our lips went wild as we got each other riled up. Soon we broke apart for a moment, out of breath as we stared into each other’s now-wild eyes. At that, I ran my fingers up from her waist over the soft skin of her stomach. I could feel her muscles spasm a bit under my touch as I continued farther up, trailing over her bare breasts to pull her shirt off. I took a moment to admire the view. To my inexperienced teenage self, Summer was a goddess on top of me, her naked skin heaving with gasps for air as a blush spread across her chest and face. Her boobs were larger than I expected, more than a handful, with firm pink nipples. There was no way she couldn’t feel my erection at this point. Slowly I reached my hand out to feel her breasts and she closed her eyes, smiling. I squeezed the soft flesh of a breast in my hand while the other arm felt up her stomach and thighs. She placed a hand over mine on her tit and encouraged me to hold it firmly as she gave a long breath out. I pinched a nipple in my fingers and she stiffened up before relaxing again, eyes now open with a fiery look in my direction. She reached out to caress my face as her hips slowly moved back and forth.
“You want more,” she said. Not as a question, but as a statement. “I’m right here.” She was so confident in her sex appeal, so confident that I wanted her so bad. She was right. And it awoke something in me.
I flipped us over and lowered Summer down onto her back under me, pinning her hands down with my own. We kissed again, passionately, before I broke it off and placed a trail of kisses down her neck and body. My lips were barely even meeting the skin, just enough to send a jolt of pleasure into her before I moved on. I passed by her boobs and kissed across her stomach, stopping at the waistband. I wanted to taste all of her sweet skin. Soon I travelled back up and circled round and round one of her breasts with my lips, getting ever so closer to the center before I took the stiffened nipple into my mouth. At that her chest heaved up into me and she let out a silent gasp.
I released my hold on her hands and took my time to caress the rest of her body as I enjoyed her boob with my mouth. I sucked and nibbled on her nipple and the surrounding skin as her breathing grew deeper and more erratic.
“There it is,” she said, her voice’s confidence now impeded by breathless gasps. “I’m yours.”
Soon I switched to the other breast as my hand fondled the one I had just left, squeezing it and trailing my fingertips around it. I started to suck on Summer’s boob without letting up as my tongue swirled around between my lips. My free hand pulled her body into me and she relaxed into my hold.
“Oh my god, my god,” she whimpered as her hands weakly gripped the hair at the back of my head and her breathing pushed her chest into my mouth. Her body pushed out and shook with the stimulation but I held her tight, tit in my mouth and hands over her bare skin, determined to show her just how much I wanted her.
I’m not sure how long I kept like that, kissing and tasting Summer’s skin as moans drifted out of her lips. I broke off from time to time to kiss up and down her body as my hands grabbed her boobs and trailed over her blushing skin. My lips met her neck, her stomach, her thighs, everywhere they could reach before always coming back to the voluptuous breasts to release another one of Summer’s moans. Primal instincts had taken over, and the only thing that existed in my mind was the desire to enjoy the sexy woman in front of me. I needed to feel, to kiss and nip at the forbidden fruit which I had been lusting over only an hour before. The pleasure escaping from Summer through her gasps and grabs only heightened my desire to give her all I could.
Eventually, in a momentary lapse as I caught my breath, Summer suddenly flipped me over so she was on top. She stared directly into my eyes with such an intensity that I was almost paralyzed. We laid like that for several moments, just looking at each other, as we cooled down and I tried to figure out what was going on.
“Wow, well that was impressive for someone whose most recent experience was 7th grade,” she finally said, running her nails under my shirt
“Well I could always use more experience.”
A sly grin crept onto her face. “Oh I know you want more.” She ran her fingers down onto my crotch and brushed ever so slightly against my rock-hard dick. It sent a rush of pleasure up my body and it was my turn for a sharp breath. Summer grabbed my hands and placed them on her breasts as my hands instinctively grabbed the soft skin. She then leaned down, until she was almost laying on me
“I’m glad you liked what you saw,” she whispered into my ear. “I think you’ve gotten enough tonight, but I’m not done with you yet. You’re going to get lots of experience from me.” At that, Summer rolled away and stood up from the bed, putting her shirt back on. We looked at the clock and saw that it was already past midnight.
“Oh yeah, you really do have to get home,” she said. She turned to me and basically pushed me out the door before pulling me in for a final kiss. My hands grabbed her ass but she soon pulled away and winked. “Keep an eye on your phone in the future.”
And that’s how I became a boob guy.
I did have to leave then, but as you might have guessed this wasn’t my last time with Summer. If this does well I might write about when we went farther.