Fuckbuddies: Glenda’s Story
Glen came over the first day of summer after graduating to play basketball and video games, like she always had while we were in high school.
Her full name was Glenda, but nobody called her that. She had always been a tomboy, and we had grown up together, exploring the woods, playing sports, and getting into trouble. It never really occurred to me to think of her as a girl, even after both of us hit puberty; she always just felt like one of the guys. She was attractive enough I guess, when I really thought about it, but she didn’t show much interest in guys or girls in high school – only in playing sports, and in winning, which she was very good at.
Today, however, she was dressed in a tight tank top that showed off her small, bra-less tits, and tiny shorts that drew my gaze to the flared thighs that puberty had given her, tomboy or not. During our daily basketball game, I noticed that she was guarding me a lot more closely than usual, even wrapping me up a few times, pressing her body tightly against mine, which was clearly a foul, and she knew it.
I’m a bit taller than Glen is, and I have about 50 pounds on her, but I still felt like I won more easily than I was accustomed to.
After the game, we went up to my room to play video games, like we always did. I plopped down in my chair, but instead of turning on the console and sitting on the bed like she usually did, Glen came over and sat on my lap, like it was the most natural thing in the world. Her fingers started tracing their way up my thigh, and I started to feel kinda funny as an enjoyable tingle started up in my crotch.
“You’re acting weird,” I accused, though I didn’t stop her.
“Am I? I dunno, we’ve enjoyed each other’s company for so long, it seemed weird not to enjoy each other’s bodies too,” she stated matter-of-factly, wiggling her hips in my lap.
“Yeah, but you’ve never seemed interested in that before. Do you want to try dating or something?”
“Heck no! Nothing so serious! I just thought you might enjoy having your dick in some pussy, and it might be kinda nice to have you inside me while we played. No pressure.”
“Wait, what? You want to have sex while we play video games?!”
“Yeah, what’s wrong with that?”
“Uh, nothing, I suppose,” I said, confused. But, my best friend seemed into it, and what she was doing with her hips was feeling pretty good, so, gift horses and all that…
“Ok, I guess we can try it out,” I answered, and she immediately hopped up to pull her panties and shorts down to her knees. I probably shouldn’t have been surprised by my dick’s natural reaction to my first sight of Glen’s tight pussy, but I was still slightly taken aback when I started to thicken and swell with desire as I bashfully pulled down my own shorts and sat back in the chair to prepare myself.
Giving me an impish grin, Glen settled down onto my cock, which slipped easily into her tight, slick wetness. It wasn’t like any of the pornos I’d seen – she didn’t move up and down my shaft or anything – she just seemed content having me inside her. After a few seconds she reached over to turn on the game console, sliding most of the way off of me in the process, grabbed our controllers, and sat back down on my lap, thrusting me satisfyingly back inside.
Once we started to play, Glen was immediately business as usual, but her movements and gyrations while playing were stimulating enough to keep me hard, and I could tell she was enjoying herself just as much from the flush of excitement on her face. Even so, Glen was always stiff competition, and I had to focus so fully on the game to stay competitive that I often forgot that my hard cock was having the time of its life buried in her tight pussy. She also kept messing with me while we played, sitting up straight so that I couldn’t see the screen, and then leaning back and forth to stay in front of me as I tried to see around her, all of which had the effect of driving my dick up into her time and time again, a feeling we both thoroughly enjoyed as we continued to jockey for position on the track.
A couple of hours later we decided to call it a night and she slipped off of me. “See? That was fun.”
I, however, was a bit frozen, unsure if I should try to lean in for a kiss or something, but Glen’s banter as she pulled her shorts back on quickly broke through any awkwardness I was feeling.
“You might want to practice tonight. If your cornering wasn’t so shit, you might have actually put up a bit of a challenge.”
“Bullshit, it says right there on the screen that I won 6 and you won 5.”
“Whatever.” She flipped me off and slammed the door behind her on her way out.
And that was what we did every day for the next few weeks. She’d come over, we’d engage in some light foreplay during basketball, and then we’d have sex for a few hours while playing video games. Glen never made it a big thing – she’d just bend over and peel off her tight shorts and underwear while I removed my own, and then the sight of her wet pussy peeking out between her toned thighs as she turned the game on would start to affect me on an instinctual level. By the time she made her way back over to me, naked from the waist down, my cock would be hard as a rock, ready and eager to slide up into my best friend. Neither of us ever came – we just enjoyed the pleasure we got out of indulging in our instinctive sexual desire for each other’s bodies. Glen clearly enjoyed feeling filled up, and, like any guy, I loved the sensation of having my dick wrapped in silky pussy.
It was weird how I never really felt the need to rectify the competing feelings I felt about Glen, how she still felt like just one of the guys despite how much sexual attraction I felt toward the half-naked woman sitting on my lap with my hard, twitching dick stuffed up her pussy. Gwen continued to treat me exactly as she always had, and watching her slide herself down onto my delighted cock so our interlocking bodies could gently stimulate each other for a few hours each night just felt… comfortable. Just two friends enjoying some casual sex while they played video games. My parents never suspected a thing.
One day as my dick slowly and intermittently throbbed with pleasure inside my best friend as we enjoyed a close game of Generic Brown Shooter 12, I asked her if anything out of the ordinary had happened toward the end of the school year.
“Actually, yeah, now that I think about it,” she said, turning around in my lap and making my dick twitch with the sudden sensation of twisting around inside her. She grinned mischievously and ground against me a few times, making me reflexively thrust up into her and causing us both to gasp in pleasure, before she settled down and continued her story. “We had just finished our last soccer game, a couple of days before graduation, and were back in the locker room getting changed when that nerd, Ed Wesley, stuck his head into the door. I remember thinking that it was odd at the time, though now I can’t really think of why it would be, since it’s only natural for a guy to want to watch women change clothes, as attracted as you horndogs are to our bodies,” she said, sticking her small chest up into my face and rolling her eyes when I immediately fixated on the clear outline of her small, firm breasts pressing through her tight tank top.
“Up here,” she said playfully, and I managed to pry my attention away from her delightful little pointy nipples and back up to her face, though my cock had suddenly gained an increased interest in my childhood best friend’s pussy that wasn’t going away. She noticed, and smirked at having proven her point so easily as she gave yet another teasing bounce on my cock, though I don’t think she quite realized the effect staring at her tits had had on me in our current condition. A pleasant tightness began to form ever so slightly in my cock, and I found myself wishing she’d bounce like that a few more times.
“Anyway, some of the girls started screaming at him for some reason, and then I remember seeing a bunch of flashes of golden light making their way around the room, covering the other girls, though it skipped me for some reason. I remember the last girl in the line looking oddly afraid, but after her glow faded she suddenly seemed just as interested in Ed’s presence as the rest of us were, unclasping the bra that she’d just finished putting on. Once all of the glowing went away, Ed asked if anyone wanted to fuck, and of course we all immediately jumped at the chance, I mean, what girl would ever turn down an offer of sex like that? I couldn’t help but strip and show off how turned on I was, and how good my pussy could make him feel.”
“‘Damn Glen, it even worked on you, huh?’ Ed said as I took my turn walking over and wrapped myself around him, feeling his erection against my waist as I jiggled my little tits for him and bent over to show off my wet pussy. ‘I forgot you were in here,’ he continued, almost guiltily as I stroked his cock and rubbed it encouragingly against my naked crotch. ‘I was just going around the room zapping everyone, and must have gotten you too. It looks like the ray really does affect all girls, even asexual tomboys.’ He finally looked down at my hips and pussy, as if seeing them for the first time. ‘You do have a pretty banging body though, now that I finally get to see it without those dumpy sweats you’re always wearing,’ he said, filling me with hope that he’d fill me with cum as he continued to eye me up and down. After a few seconds, however, he turned his attention back to the other girls. ‘Oh well, enjoy your new craving for dick, I guess. No one will confuse you for a guy after this.’
“I didn’t know what all of that meant, and I still obviously wanted to have sex with him, but I was oddly relieved when he narrowed his choice down to a few other girls who were more the cheerleader type, with bigger tits. I guess as much as I wanted to feel Ed’s dick inside me, and still do, I didn’t really look forward to having sex with him for some reason, though of course I would have if he had picked me.
“He eventually chose Trish, who immediately mounted him and slid his hard little cock as deep as it could go into her lucky, slutty pussy. The other girls stuck around to rub their breasts in his face and beg him to fuck them next, but once I saw that Trish was well on her way toward filling her fertile young pussy with Ed’s cum, I got dressed and headed out.
“I was still pretty overwhelmed with that familiar, intense need for cock that I always get whenever someone mentions sex around me, so after I got home, I remembered what Ed had said about my clothes, changed into a more revealing outfit I thought you might like, and came over to see if you’d be interested instead. And I guess Ed was right about my body, because as soon as you saw these hips naked you immediately started thinking with your dick, our friendship went out the window, and I became just another slutty piece of ass willing to let you fulfill your stereotypical male urge to stick your cock inside her,” she teased, but I could still see the trepidation behind her smirk, even as she slowly rocked her hips back and forth and we both continued to enjoy the feeling of my cock sliding around inside her slick, stimulating pussy.
“Bullshit Glen,” I said. “You’re the one who suggested doing this in the first place, and if anything, you’re the one catching feelings here. You were beating me 7 out of 10 easy in this game a month ago, but now I’m taking better than 50%.”
She looked up at me in silent gratitude, and we both focused on the sensations of how good casual sex with your best friend could feel for a few seconds, before I continued the conversation.
“And ever since then you’ve wanted to have sex with me?” I asked, glad she felt so comfortable talking about such personal subjects around me, especially with the odd, almost supernatural nature of what had gone down in the locker room. I made a mental note to go find Ed and find out what really happened that day, because Glen’s story was pretty messed up.
“No, I’m sure it was before then too… I just never acted on it for some reason,” she responded, wiggling her sexy hips in my lap and flushing a bit as her antics caused my dick to twitch again deep inside her. Once more I was briefly struck by how strange it was to be fucking someone I thought of as one of the guys, but then I glanced down at her waist and hips and felt her firm, toned butt bouncing in my lap. My cock immediately remembered why it was so interested in her, and the pleasant tightness in my groin began to slowly intensify.
She continued. “I mean, it’s perfectly natural to want to have sex. My body has been driving me, practically compelling me to fill it with cock ever since I became a woman… And there wasn’t ever really a reason not to; it’s just that the timing just never seemed to be quite right, though I definitely would have given it up in a hurry if anyone had just straight up asked before Ed finally did.” She gave me a reproachful look, though her words weren’t matching my impressions of her at all as we went through our teenage years together.
“So why did you never have any boyfriends, if you wanted to have sex so much?” I asked, setting my controller down to wrap my hands around her smooth waist, which she seemed to enjoy as much as I did.
“I dunno, I guess I just never felt like I had a connection with any other guys. Not that I would turn dick down – what woman could possibly do that? – I just didn’t really feel like seeking it out, as much as I wanted to, even though I knew that the guys would be willing. I mean, I would definitely fuck pretty much any guy if they asked me to,” she continued as my eyes widened with surprise at the brazenness of her statement, “but I’m kinda glad they didn’t. Yeah, I dunno, it just feels right with you for some reason,” she said. “It’s like I finally get to share and enjoy an irresistible compulsion I’ve always had, with my best friend, while knowing that I don’t have to worry about anything.”
As she looked down at me, the pupils of her beautiful green eyes dilated a bit, and I realized for the first time just how beautiful she was.
“So, you’d fuck any guy who asked you, huh?”
“Of course! I’d practically be compelled to. I wouldn’t be able to say no…” she trailed off, and her eyes got large and liquid as we both remembered the pleasurable sensations coming from our already conjoined bodies.
“Glen?”
“Yes?” she answered, eyes wide and hopeful, sticking out her chest a bit as my gaze dropped to the pert breasts and hard nipples clearly visible through her tank top.
“Would you like to fuck me?”
“Oh God yes!” she moaned. Her hopeful look was immediately replaced by one of intense need, almost animalistic compulsion, and she lifted her torso up with her powerful thighs and slammed it back down around my dick as she ripped her shirt off and her delightful little titties came into view. I saw the hunger in her eyes as her body automatically began doing what came most naturally to it, squeezing my cock in her tight, slick pussy as she stroked herself up and down my shaft, pleasuring herself with the internal stimulation as her actions began to lead toward my inevitable ejaculation. Finally getting the fucking she craved quickly proved too much for her, and she soon fell against me as her toned body began to rhythmically clench in orgasm.
My dick’s twitching was getting more and more insistent inside her as she came down from her climax. I started to warn her, but she said “Miss me with that weak-ass pull-out shit. I’ve already got mine, and we both know we’re going to enjoy what’s about to happen,” she said, breathing heavily as her words and slick friction took me right up to the edge.
I was looking up into her eyes, into her beautiful face flushed with pleasure, and before I knew what was happening she was leaning down, and our lips met. She tasted wonderful. My dick eagerly slid deep into her pussy one time too many, and suddenly it began to feel even better inside her than it had before as I felt myself losing control. Everything just felt too good, her pussy game was too strong, and I couldn’t stop my balls from tightening or my cock from stiffening, and then I was spurting up inside my tomboy best friend’s pussy as she continued to ride me, her strong core muscles flexing, keeping up the stimulation that was filling her with burst after burst of my semen as I helplessly rode out the deep, pleasurable contractions of my orgasm. Glen held the kiss while our tongues and torsos danced, and I caught feelings as I continued to throb inside of her, now mostly spent.
She slowed her pace as my dick finally started to go limp, and then broke the kiss and stood up.
“You know this doesn’t change anything,” she said, punching me in the shoulder hard enough to bruise, before turning off the forgotten game console and heading toward the door, my cum forming a wet patch in the crotch of her tiny shorts once she pulled them back on. “I’m still going to kick your ass in Crossover Mascot Battle tomorrow night!”
“Do you wanna go, uh, grab some pizza together first?” I asked sheepishly.
A smile slowly spread across her face, still flushed from her recent orgasm. “Yeah, I think I’d like that.”
Author’s Note: Thanks for reading! If you have any feedback, comments, or questions, I’d love to hear from you! If you enjoyed this story so much you’d like to support my work on Patreon, my profile is easy to find on Google (Sexstories doesn’t like personal links). Patrons get early access to my stories, input into which stories I write, and some fun other perks. Every little bit helps, and your support is what enables me to keep doing what I love!