We have a friend named Katelyn from our college days who used to live with us in an apartment we owned in downtown Boston. She was a sexual sort of person -- the kind of girl who would major in sex if she could. Not that she was promiscuous -- not by any means. She just enjoyed giving and recieving and she loved to make her lovers happy.
She was fairly celibate while living with Jon and I, but after a few months of carefully avoiding the topic of sex and a few walk-ins by her on us naked in bed, occasionally someone would broach the subject. Katelyn and I would talk a lot about kissing, and how much more we preferred girls' kisses. We became "kissing buddies" one day after Jon walked in on us kissing. He didn't mind it, as long as it didn't go farther, and sometimes when he was licking my pussy I'd fantasize he was Katelyn and on those nights my orgasms were better than ever.
He didn't know why then, but one day, he'd find out. She and I were talking while he was out one day, and somehow we got onto the topic of our pussies. Katelyn wondered who was tighter, and the way she put it, there wasn't really much I could say but "Jon should judge." A week or two later, I was walking down the hallway, about to go to my room, when I heard her sweet voice ask, "Jon, do you think I'm tighter than Tiffany?" I can only imagine the blush that graced his cheeks as she asked him, and his flustered response to the question.
Later, Katelyn told me that he looked redder than a fire truck, and that she managed to cajole him into inserting a finger into her. I laughed when she told me this, knowing exactly how my boyfriend was back then. I still have no idea how she did it, but I think part of it was the way she looked. Her hair was gorgeous when loose, and that day it fell in thick golden brown waves over her shoulders. She was wearing a white and baby-blue striped polo shirt. It was one I'd given to her for her birthday a few weeks before, and I remember admiring her tits when she wore it. She had beautiful breasts, C cups that were as perky at 22 as they were at 16. Jon has a thing for girls wearing underwear stretched tightly across their crotch, putting their labia into high relief, and that day, Katelyn was wearing a pair of white string bikini style underwear that were probably a half-size too small for her. She'd planned everything perfectly to seduce my boyfriend and I'm not surprised he'd relented. It would have taken far less to break my resolve when it came to Katelyn.
I asked Jon in bed that night who was tighter, and he blushed furiously. Very quietly he said "You are...but she's pretty close." I laughed at that and he probably thought I was crazy. I told him, "We put you up to that, babe. She wanted to know who was tighter and I offered you up as a judge." He was kind of mad at me for that, but the sex we had that night was fantastic. I think he was pretty okay with us for tricking him into fingering Katelyn after that.
A few weeks later, Katelyn and I were making dinner and we shared a fairly hot kiss as the water was boiling. Jon happened to see Katelyn pressing me against the counter as we kissed fiercely and he told me about his reaction to it that night. "I wished I was her, but watching you two going at it like that was just too sexy for me to get involved in. I was pretty hard though, watching the two of you. I wanted to take you away right after you finished kissing and just have my way with you.
"I would take you into our room, already putting my hands into your underwear and making sure you were nice and wet by the time we got to the bed. I'd lay you down..." here he sighed happily, rubbing his crotch "...and I would kiss you and then bring you to your first orgasm. You would moan my name loudly and let Katelyn know exactly what was going on...oh god, Tiffany, don't stop...and then I would take my fingers out and your underwear off and fill your pussy with my cock. Would you like that?"
I nodded breathlessly. I could feel myself getting wetter and wetter as he spoke. I'd started playing with his balls as he talked, knowing how much he loved when I did that. "I would fuck you hard and fast, and you'd play with your clit as I fucked you...god DAMN Tiffany, are you trying to make me cum already? I haven't even gotten to the good part!"
