My Best Friend's Girl

It was difficult to concentrate on anything. Visions of Aileen's nude body beneath me, hands tied above her head, strapped to my bed post, back arched and breasts thrusting out to meet my insatiable lips interrupted my thoughts constantly.

It was only a few hours ago. Aileen was at work, doing the late shift at the grocery store; probably with my cum still leaking out of her pussy. And yet reality kept jolting me awake. I'd betrayed my best friend by having the most wondrous sex of my life with his girlfriend. And she'd just announced that she was going to leave town in a week. It made logical sense. A partial scholarship to a reputable school was the logical decision to make. As I dropped her off at work she'd mentioned that she didn't think she and John would be able to make the long distance thing work; that it may have to end this week. But even that would be difficult. John wasn't due back until a couple days after she was moving. As I said earlier, Aileen was full of secrets. And my head was still whirling at all the various ways my life was changing because of one magnificent hour of passion.

It was getting late and I went back home in a futile attempt to sleep. The next day - attempting to play it cool, I didn't call her. But then she didn't call me. Did I waste a day? Should I be calling her? Shouldn't I let her work things out with John first? I was so conflicted. I had no idea what to do or think.

Two days after our magical tryst, Aileen called me. She was a bit perturbed I didn't call, but her the annoyance in her voice soon gave way to some flirting and our usual easy banter. "Can you drop by my place? My parents are working at the restaurant and I need someone to help me drive some stuff to the bus station. I'm going to be shipping some of my stuff to the university dorm by Greyhound bus," Aileen said.

I got to her place in record time. After helping her drop off a few boxes I had to ask, "What's happening between you and John? Have you told him you're moving yet? Did you tell him what happened between us?

"Yes, I told him I'm going away for school. The timing is awful, we won't have a chance to really figure things out. But you know him. Within a month he'll have replaced me with some other girl, one who's skinnier, with bigger boobs, and a nicer butt." Aileen was only half joking. I thought the same thing. John was always smooth with the ladies.

"Well I don't think he'll ever find a better person," I sincerely replied. "Beauty is more than what's on the surface. Plus, I think your boobs are pretty good already..." Maybe I shouldn't have added that last part.

Aileen laughed, the twinkling mischief returning to her eyes, adding, "You know, I think I still get my turn."

"What do you mean? Your turn?" I was intrigued and a bit scared.

"You had me tied up and I couldn't do a thing. I think it's my turn to take over!", Aileen said.

We had just pulled in to her driveway and my cock was starting to stir. "I don't know if that's a good idea. You and John need to figure things out, I don't want to be the one coming between my best friend and his girl."

"Well I think you've already come between your best friend and his girl... what's one more time? Plus I'm serious! I want my turn! You gotta play fair!". Aileen was insistent. And who am I to oppose fair play?

She sent me off to the corner store to buy condoms and she wanted to clean up the house. When I returned, she let me in. Her parents were working at the family restaurant and normally wouldn't be back by midnight. Her brother spent most of his waking hours at his girlfriend's place so we'd have the place to ourselves.

"Come with me!" she giggled, leading me by the hand to her room.

She grabbed a couple of her brothers neck ties from his room. While walking past I couldn't help but notice a few porno mags on the bed, a tv and a vcr at one end of the bedroom along with a few video tapes scattered throughout (yes, this took place in the 90s). "My brother has a bit of a porn habit," Aileen said with a very matter-of-fact tone. This girl has so many secrets!

Walking into her room she playfully pushed me onto her bed, tying my hands together to the top of her bedpost as I had done to her a couple days previous. But she had to one-up me... she tied the other necktie around my eyes so that I couldn't see. Her brother's aftershave was quite strong, I could even smell it on the tie.

Aileen was thoroughly in charge now... stroking my arms as I did to her before moving lower and lower, caressing my face, pausing to give me the occasional peck on the cheek, or on the ear, or on my lips. Her fingers began to stray towards my chest, stroking the fabric of my t-shirt, making small circles around my hardening nipples. She began to pull my shirt upwards, kissing my belly, and licking my belly button as I had done to her. My cock was getting harder and my mind was beginning to lose focus. Before I knew it my pants and briefs were gone, my entire lower body exposed to the air.

"I never had a chance to really enjoy this last time," Aileen whispered. She slowly stroked my legs. She complimented my legs many times and now as she stroked my inner thighs, I knew she wasn't stopping there. My cock was at attention as she gave it a quick lick, followed by another. There was some rustling on the bed, the sound of footsteps and clothing dropping. Before I could say anything I heard Aileen tearing open the box of condoms...

"Just want to be safe - don't want to get carried away like last time." Her fingers kept teasing my cock over the circumsized head before she slowly slipped the condom on. She began licking the inside of my leg, and then moved up, kissing up my body before reaching my lips. I began to try kissing her but she continued moving upwards until my lips were brushing up against what could only be her breasts. How I wish I could have seen them! I imagined them as last time - her white breasts, hanging on her body, quite heavy but not overly large. Her black hair was swaying, brushing up against my head as her breasts lingered above my lips. I gave her nipples a few licks, making them point out more.

She returned back to the lower levels and began kissing my cock. As she began licking and sucking it, the sensation was muted somewhat by the condom, but I wasn't going to complain. I could feel the passion rising, my balls were beginning to stir... Her hand holding on to my cock as she licked. Her other hand caressing the inside of my hips. It seemed like her hands were everywhere, all at once.

"Your hands are magical... feels like you're all over me at once..."

"Such a silly goose!" Aileen replied.

Aileen's began to rub her pussy over my cock, stroking it with her outer lips, back and forth. She slowly lowered herself on to my hardened cock. I could hear the squishing noises, she must've gotten herself wet. Her gyrating started slow and methodical but was beginning to increase in pace as I heard her breathing getting faster and faster. My blindfold was starting to come off and just as we both approached orgasm I could see... Aileen's breasts, flopping as she rode hard up and down, her eyes, closed, and her hands holding on to my chest. My hips were thrusting upwards to meet her. I pulled my hands free of the necktie and reached up to squeeze her breasts.

My cock exploded, cum filling the inside of my condom. Aileen's face and body were flush and her spasming began to slow down as she starting coming down from her orgasm... My eyes reopened to see Aileen's best friend Kitty, standing at the foot of the bed, behind Aileen.

It took quite a while for me to compose myself to blurt out, "What's going on?"

Aileen giggled and explained. She had told Kitty everything. Kitty was very curious as her own sexual experiences with her ex-boyfriend were far from satisfying. Aileen had planned all along to have another farewell sex session with me. But I didn't know it. And Aileen had intended to invite Kitty over to her place to catch us in the act, but didn't let Kitty know. Kitty, let herself in and followed our sounds to Aileen's bedroom. She had been watching the whole time. The hands stroking my inner thighs while Aileen worked my cock belonged to Kitty.

Aileen was quickly recovering from our session and untied my hands, kissing me on the neck, on the cheek, and finally on my lips. She then stood up, still naked with a coat of sweat on her skin, stood next to Kitty, whispering in her ear. The contrast between the two never more apparent than now. Aileen was taller and had a stockier build. She was not fat but did have some extra meat on her. Kitty was at aerobics class three times a week. She was wearing a tank top that showed off her thin frame, her cinnamon coloured skin, her toned arms, and a hint of cleavage. Her breasts looked so firm underneath that tank top. Her shorts showed off her thin, toned legs... Her face was round, she had a baby face - hence her nickname "Kitty" versus her legal name of Catherine.

Kitty giggled after hearing Aileen's whispers... I tried to cover up, reaching for my pants, but Aileen stopped me, the sparkle in her eyes magnified by a healthy dose of mischief. "How about a farewell present for both of you? Believe it or not, Kitty had a crush on you too and I think after that horrible ex-boyfriend of hers ruined her, I think someone needs to make love to her properly. And I can't think of a better teacher."

Kitty began blushing. Her large eyes, looking at my naked body, looking aroused, yet timid. I stood up and softly asked, "Kitty, do you really want this?" I reached out and held Aileen's hand as well as hers.

She looked away, let go but then returned my gaze before whispering, "... only if you do..."

I leaned over slowly and gave her a light kiss on the lips. Her lips were fuller than Aileen's. Aileen had put on a robe and sat on a chair against the wall, watching as our short kisses slowly increased in duration and passion. I reached up and stroked the side of Kitty's cheeks.

"Do you trust me?", I asked. Kitty nodded.

"I promise to take good care of you... don't be shy... let yourself be swept up in the moment...", I quietly said in her ear. I took both her hands as I continued kissing her cheek, her ear, down the nape of her neck. She was gorgeous. I slowly removed her tank top and bra, revealing a perfect body. She could have been in Playboy magazine. Thin waist, wider hips, beautiful firm breasts, rounder than Aileen's though not as large. But her firmness and the fact that they were slightly closer together than Aileen's gave her a more natural looking cleavage. Her nipples were puffy, whereas Aileen had pointy nipples. My cock started to revive while staring at this goddess before me.

Kitty's golden skin was in contrast to Aileen's very light complexion. But both had amazingly smooth skin with great complexion. I started kissing Kitty's fingertips as I held her hands together. I moved slowly up her forearms, biceps, and then lingered on her neck and shoulder. I pulled her arms to her sides, pulling myself closer to her, feeling her naked breasts brushing up against my chest. I moved slightly, side to side, feeling those puffy nipples against my skin. I kissed down her shoulder and began exploring her breasts, savouring every inch.

My hands kept busy by slowly removing her shorts and panties. The smell of her wetness, coming from her pussy was beginning to grow stronger. I licked her puffy nipples, seeing them grow harder, right before my eyes. I looked up at her and her eyes were closed, she was truly lost in the moment. I stood back up and helped lower her on to the bed, resuming my worship of her breasts, one hand caressing, my lips and tongue tasting the other breast, and my free hand feeling her thighs, her butt, and then lingering between her legs, slowly stroking her pussy lips. Her hands began to roam my back feeling my down towards my butt... She let out a sigh as my finger began to stroke her clit. She maneuvered her hand beneath me to find my swollen cock and she began stroking it.

Aileen drew closer, reaching out her hand and helped put my condom on. She then reached out and held one of Kitty's hands as I slowly stroked my cock on the outside of her pussy lips. I took my free hand and began caressing Kitty's flat stomach, lingering on her belly button before moving lower to her clit. The wetness from her pussy lips made it easy for me to slide my cock head in, but I wanted to be slow and gentle. I slowly moved the head in and out of her outer lips, going ever so slightly deeper each time. Her pussy felt tight as I dug deeper and finally I was all the way in. A sigh escaped her lips and she reached up, grabbed me down to kiss her as I slowly worked my cock in and out of her vagina.

Aileen was right next to us, stroking my buttocks, caressing Kitty's arm as Kitty and I kissed. I pulled back and turned to kiss Aileen, taking her hand and placing it on Kitty's breast. I pulled my cock out, lowered my head to her other breast and began sucking on her nipple while my left middle finger began fingering her wet cunt. Aileen lowered herself to kiss Kitty on the neck while caressing Kitty's nipple. Kitty's eyes were closed now and her back began to arch, her pussy reaching out to meet my finger... I withdrew it and replaced it with my cock again, this time thrusting with more urgency. I leaned back, watching her breasts jiggling as I pumped her faster. I pulled her arms down to meet my groin, watching her breasts press together. Now it was Aileen's turn to reach down and kiss her nipples, alternating between licking and sucking.

Kitty let out a loud moan, her hips starting to thrust more wildly, I released my grip on her wrists and she grabbed on to the sheets of the bed, lost in the throes of her orgasm. I slowed down the pace before slowly withdrawing, her pussy felt hot and wet.

I had not yet cum... my first session with Aileen had given me a lot more staying power. I pulled out, put on a new condom and grabbed Aileen closer to me, turning her over so that her ass was facing me as she kneeled on the bed on all fours, on top of Kitty. As the two of them started sharing a kiss I plunged into Aileen's pussy, still wet from before and perhaps from the arousal of watching Kitty and I have sex. I leaned over to grab her breasts, but let go of one hand to caress Kitty's breast at the same time. Unfortunately I was unable to maintain this position for long without losing my losing my depth in Aileen's pussy. So I leaned back and concentrated on pounding her in doggy style from behind. Watching the two beauties kissing below me, breasts rubbing against each other, my hand stroking her back, brought me to my orgasm at last. I pulled out, exhausted.

The three of us lay on the bed, spent. Our breathing was ragged, our bodies were sweaty, and as we looked into each other's eyes we could all see that something magical had just taken place.