"Mattie, relax," Ann said. "People have been doing this for centuries, you know. It's no big mystery."
Mattie opened her eyes, looed down, and saw my erect cock, the tip just a half inch away from where her labia parted. "It's going to hurt.
He's too big. He's twice, three times the size of Phillip. I'm scared."
Ann reached down and fingered Mattie's pussy a little. "You're also as wet as Seattle, girl. He'll take his time. You'll like it. Just try to relax your muscles."
Ann moved out of the way and I moved up, touching my cockhead to her clit. Mattie jumped a little, then closed her eyes again. I began to run the head of my cock up and down her slit, feeling her get wetter and wetter, and watching her small labia begin to part.
"OK," she said, breathing in through her nose and out through her mouth, her bit breasts heaving with each breath. "OK, but slowly, please. Take it…take it slowly…"
I pushed just the head of my cock into her pussy, and we both jerked.
Mattie let out a little yelp of pain, but I had jerked at the pleasure of how incredibly tight she was. Ann had a terrific pussy, but Mattie's was like a vise. I began to wonder myself if this was going to work.
I began to rock back and forth, slowly, letting the head of my cock slip in and out of her cunt. After a while, she got into it, pointing her toes and rocking her hips. Her lips were slightly parted and her breathing was deep and slow. I reached down with my thumb and stroked her clit a few times and she moaned. Ann began to stroke her breasts, pulling and tweaking her nipples, and Mattie smiled ever so slightly.
We kept this up for a long while, me just barly penetrating her while stroking her clit, while Ann sucked and stroked her nipples. I had reached around with my free hand to stroke Ann's pussy for a while, but she moved out of reach. She wanted me to concentrate on her friend.
After a time Mattie's pussy felt a little looser. Not much, but I assumed it was all I was going to get until I pried it open myself. I let my cock slide in about an inch, maybe less. Again, Mattie and I gasped together. This was like trying to fuck a soda straw. I could feel that my cockhead was hitting her hymen – it felt like a little string streched from one pussy wall to the other. I began to press against it on each stroke, and Mattie really began to feel it.
"Uh, oh God Ann he's too much. Oh, no, no, he's t-t-tearing me apart.
Oh, easy, oh, God, Ann please please, oh…"
Then her hymen broke, and my cock slid in another inch.
Mattie screamed. I stopped all progress, but did not pull out. Ann began to stroke her face and kiss her. "That was the worst part, Mattie, and it's over."
Tears were streaming down her face. "That was m-my ch-cherry, Ann?"
"Yes. It's gone, love." Ann smiled warmly at her.
Mattie's tears flowed as she stared back at Ann. I looked down at my cock, most of it still outside, and wondered.
"Look, Mattie, if this is too much for you…" I began, but Mattie cut me off.
"No," she said, smiling now, staring at Ann's face, "we've gone this far. Let's do it."
I leaned over, took a nipple in my mouth, and began to fuck her, Shallowly at first, of course, but with a clear intention to bury my dick in her tight pussy.
I swear it took an hour. Every half inch I gained took her five minues to get use to. She was holding my head to her breast, and grasping Ann's hand in hers. By the time I was halfway in, she was coming in a long stream of little orgasms.
"Ommmmmmmmmmmmmmm, Oh, Ann it's so… ohhhhhhhhhhh God it's so good…"
Finally, I took a deep breath and slid my dick all the way to the hilt.
Mattie grimaced and hissed in a deep breath, but she did not scream. I began to fuck her for real.
Mattie's pussy was the most fantastic thing I had ever felt. It was this perfect, smooth, tight velvet sheath. The soft little hairs, invisible to the eye, that surrounded her tiny hole were tickling my balls on every stroke. Every time Mattie moved her leg or twiched her hips I felt the virbrations on every molecule of my cock. I swear I could even feel the vibrations of her heartbeat through that incredible pussy.
When I was finally ready to come, Mattie was rocking her hips violently and clasping her legs behind my butt, pulling me in. She looked barely conscious, her eyelids fluttering, her eyes rolling around, her face very white.
I was in pure ecstasy. It was like she had me in her fist, and was squeezing with all her might, except that this fist was soft and yeilding; the smoothest, wettest, warmest thing on earth.
Mattie rolled into another orgasm, this one the biggest of all, her back arching, her thighs tense as steel. Her voice was a whisper building to a scream: "Ahhhhhhhhhhhhhh, Yesssssssssss, oh, fuck fuck fuck fuck…" Then her thighs began to relax, though she was still coming and coming.
"I'm goign to come, Ann, " I said, and Ann deftly leaned over us and slipped my cock from Matties pussy, in the same motion sliding it into her mouth. We didn't want to get Mattie pregnant, but I had to moan a little at leaving that perfect hole.
Mattie groaned and Ann began to finger her, to finish off her orgasm while I came in her mouth. My cock pulsed and jumped in her hand, and I poured what felt like muy entire being out through my dick and into her mouth. She moaned, swallowing every drop, then motioned for me to suck Mattie's pussy until she finished coming, which I gladly did.
We collapsed into a heap after that, Mattie on her back, Ann resting her head on Mattie's left breast, me lieing between Mattie's spread legs, resting my head on her pussy hair. We slept for a while, utterly sated.
When I awoke, I rose and put my shorts back on. I checked the clock:
We'd fucked for an hour and then slept for two.
"Where are you going," Ann said, rubbing her eyes.
"Don't leave," Mattie said, a pleading in her voice, her eyes staring at my crotch.
I smiled. "Don't worry, girls. I'm just going to go downstairs and fix us all something to eat. You two can relax and… whatever."
"What's next?" Ann asked, smiling sleepily. "You said something about a fantasy?"
I had to think for a moment – oh yes, I'd told Ann I'd had a fantasy about tit-fucking Mattie. I was just being sarcastic when I said that, but looking at Mattie there on the bed, her big tits shifting their weight as she breathed, I could imagine my dick sliding between those glorious melons and into her now-educated mouth. Not a bad idea.
"Yeah," I said, "Maybe you can get things, uh, ready for me, Ann."
She smiled and began to lick between those incredible tits, to show me that she knew what I mean.
As I left the room, I heard Mattie say:
"Oh, thank you Ann. God, that was great. You were so right. Do you think he'll fuck me again? How can I ever repay you?"
I heard them moving and Mattie giggled brightly.
"Right here," Ann said. "Lick me right here…"
So,
The queen of the high school elite was mine, and now she had given me one of her ladies-in-waiting to play with. Ann arranged to get the pill for Mattie, who was eager to feel me come inside her since Ann had descrived the experience so glowingly to her. For the rest of the school year, and most of the summer that followed, Ann, Mattie, and I enjoyed a sexual romp. Ann and I did bring Mattie into our secret apartment, since she seemed totally won over to us, and we spent many an afternoon, all three of us fucking and sucking and coming. Our senior grades were not the best, but it was sure worth it.
During that time I found that Mattie and I got closer and closer, in bed and out. Ann understood this, perhaps better than we did, and seemed to encourage it. Mattie fell in love with me, and I thought that I might be feeling something for her too.
After the summer that followed graduation, Ann's family sent her to a high-priced college in the east. She did not protest, knowing that something was growing between Mattie and I. At first, she'd come back for all the holidays and the three of us would meet at the apartment for an afternoon of sex. Those were some of the best sessions ever – absence makes the heart grow fonder, I guess, and Ann was learning all sorts of new things at the frat parties she was attending. She even started wanting me to fuck her in the ass, though we only did that once, Mattie refusing to try it after seeing what Ann went through.