A Never Simple Encounter

I shouldn't have done it. Or her, more specifically. I knew it, I took advantage, and did it. I am happy for how things turned out, mostly, but it was still wrong.

I was a senior in college, former president of my fraternity but now lived off campus in a small apartment. Claire was a freshman and roommate with Megan, who was a junior and president of our "Little Sister" program. Claire was homeschooled, barely 18, and cute in her innocence and looks. Megan was sort of butch but pretty when she wanted to be, a former lover of mine, and bisexual.

But now Megan informed me of the crush her new roomie had on me.

"John, you have to be gentle with her," Megan said. Ever since you helped me move in she has been talking about you. 'Oh, he's cute', He's dreamy,' 'He's sooooo funny...' I told her as president of the Li'l Sisses, there were rules...but, if YOU take her to YOUR place and fuck her silly, no one has to know."

"Meg, I don't know. She's cute, but a freshman. Mostly I don't want to sneak around, though," I said. There were rules to dating the Little Sisters, and they weren't tough. Mainly the Sisters were supposed to be friends and off limits. The program wasn't supposed to be a prostitution ring. However, their friends were fair game and fresh meat.

"I don't know. Sex complicates things," I said, setting off our prearranged commentary.

"It didn't affect us, did it, John?"

I met Meg at the Rec Center while playing racquetball. I barely beat her, walked her home, fucked her, and then found out she was gay. But she did like fucking me. Emotionally we could never be a dating couple, but did love each other. So, yeah, even though we were still good friends, our relationship was somewhat complicated.

"Well, even though we are perfect for each other, we still don't-"

"We have too much in common, John. Remember, we both like pussy too much," she would say. That would make me think about how she taught me how to be a cunnilingus master.

"I don't know..." I'd say, right before I gave in.

"So meet her for a meal. Don't have sex. If you like her, announce to me and The New Guy President that you want to 'date'. Then you are fine. It's ethical, Mister Boy Scout."

"Fine, what's her number?"

*************************

Claire and I met for supper at a local restaurant that was popular and quiet. We talked and had a great time. I really liked her. For an 18 year old, she had a brilliant mind and could talk at length on almost anything. She had brilliant blue eyes that sparkled when she spoke and her smile was genuine and kind. Her voice was like a songbird and I felt myself really wanting her. But not tonight. I had ethics. And character counts.

I walked her home and we held hands. When I got her to her dorm room, Megan was waiting for us. "Did you kids have fun?" she asked in her motherly yet stern voice.

"Yes'm," I joked. "And I had her home before 9pm, just like you said."

Claire chuckled. "He was a gentleman. He didn't even kiss me...yet," she said, and licked her lips and winked at me.

"Hmm, let me see, I left a...something around here," as Meg turned her back, allowing us a kiss in the hallway.

Claire had the softest lips, and even after dinner her lips tasted like berries. Her tongue darted into my mouth and they did a tango. I knew at that instant I was going to "declare" that we were dating. I HAD to have more of her!

That next weekend was Homecoming Week. Since I didn't live in the fraternity anymore I didn't participate in most of the activities- which was good because school took its toll that week. Claire was prohibited from more than 8 hours of floats and other activities that week because she was a first semester student. Meg was busy, but I didn't spend much time with Claire. Our big turn would be this Saturday.

We went to the football game together, tailgating before. My friends really liked her and teased her about dating an old man. After the game I dropped her off, promising to let her get ready and would pick her up in 2 hours and we would hit a few parties, and "see where the night took us." I think we both knew that answer.

Meg had called in that 2 hour window. "Dude, what are you two gonna do tonight?"

"I think we both have about the same idea," I said.

"She is a virgin. I helped her- I helped her pop her cherry, but she is still a virgin, so be gentle. Just like I was with you," she teased.

I was a little let down. A true vigin would have been nice, but also the first time is usually messy and sore and not a lot of fun. But at least the awkward part was done.

"Thanks for the intel, Meg. What are your plans?"

"If you take Claire back to your place, maybe I will get some pussy or dick- or both- and bring 'em here."

I shook my head. She was a big talker, but wouldn't do that. Would she?

"If she is open to it, we will come here," I said.

"Oh, she 'OPEN' to it, allright!" as she laughed and hung up.

**********************

Claire and I went to my fraternity's homecoming party. We danced, we had a couple of beers. She started slow dancing with me even though the song was fast, snd she whispered

into my ear, "Let's get out of here." Gladly I complied.

"Where to?" I asked.

"Let's walk by Swan Lake, and maybe head back to your place," she said, determination in her voice.

Swan Lake was a pond near central campus and it had a footbridge to an island. Legend says if you kiss your sweetheart at midnight on homecoming, you would live happily ever after together. I wasn't ready for THAT with Claire just yet. And it was barely 8pm.

But there is another more secluded part of the lake where people like to make out. That was less legendary and more scandalous...

We got close to the secluded spot and saw two other couples there, one having full blown sex and the other couple was she giving him a blowjob. Claire became a little nervous and squeezed my hand tightly and whispered, "I've heard about this going on here. Can we go back to your place?"

"Sure thing. Need to pick anything up on the way back?"

"Nope. Just me, if you like," she teased. I scooped her up and spun her around but set her back down.

Claire was about 5' 7"- not too tall, not heavy, great, fit body. Reddish blonde hair, nice curves, beautiful green eyes. I am 6 foot tall, 175 pounds, fit, brown hair, and probably could have carried her the 7 or 8 blocks back to my place if I had needed to, but probably would have been spent by the time I got there.

We walked, hand in hand, and her pace was quick. I had to kick it in to keep up with her. She wanted this and it became apparent I was not the instigator.

Whe went though the security door, up the first flight of stairs, turned down the hallway towards my place. Loud music, loud sports, laughing, singing- lots of ambient noise going on. I hoped it would not kill the mood...

"Now you can carry me. Carry me into your room and lay me down on the bed," she said.

I picked her up, her knees over my left elbow, her arms around my neck, and she kissed me. Not chastely, but not lustful either.

"Just so you know, I am not a virgin, but I don't have the, um, 'experience', that you may have. I want to give myself to you, and I hope you treat me the same way in return," she said.

I remembered back to Meg saying that she had helped Claire pop her cherry but that Claire had never actually had sex. The thought of Meg using a vibrator or dildo on Claire- naked, breathing heavy, slowly penetrating her pussy, saying shit like, "Oh god, it hurts, oh, now it's soo good. Lick me Meg! Suck my clit!" while Meg, naked herself, was riding the Sybian while licking Claire and both of them squirting simultaneously...

Anyway, fantasy aside, I knew Claire wanted me to make love to her and treat her special. I didn't have a lot of experience myself, but Meg did teach me a few things. Why that never worked out, who knows.

So, I was determined to treat Claire like she was special and it was our wedding night. I liked her a lot from our date, but wasn't toally in love with her. But I did respect her, and wanted to treat her like she deserved to be treated. No cumming in her eyes and laughing. No emotional abuse. No punishing sex. I wanted her to love making love with me, because I liked the idea about more sex with her.

So with Claire standing before me just inside my apartment, both of us clothed, our eyes almost level with each other. I wrapped my arms around her and kissed her deeply. Our tongues touched and we both gasped. Then I kicked off my shoes. She responded by putting her hand on my shoulder and I grabbed her arm fo support as she took oh her low heels. She settled in a few inches shorter now, and we kissed again. She tossed her head back, whipping her hair and I went in for her neck. No marks, no hickies, just a sensual kiss and she moaned again. I kissed down to the buttons on her blouse and kissed her cleavage above the black, lacy bra. "More," she whispered.

I pulled back and whipped my shirt off, and went in for her buttons. I fumbled with her first button, and she responded by gripping her blouse and ripping it open, sending a couple of buttons flying.

Fucking hot! I thought. I felt her breasts that were bigger than I though, and the tops of her areolas were peaking out of the bra that was designed more for arousal than containment.

I have a small apartment but it does have a nice kitchen/ dining room area. I picked her up, and she wrapped her stocking-clad legs around my waist. I moved her over to the kitchen island and sat her butt down, and she laid back, propped up on her elbows, waiting for my next move.

I got underneath her skirt, noticing her matching black lace thong and thigh high stockings. No garters. I took a whiff of her musky aroma and assumed correctly that she was soaked. I pulled the stretchy fabric to the side and noticed her trimmed pussy. It was shaved except for a tiny strip. It looked exactly how Meg trimmed hers. Meg really knew how to look out for me.

Her lips were mauve or some shade of brown or pink- some fancy color on the color wheel I can't name, but I knew from their swollen dripping that she was highly aroused. A string of pussy saliva was dripping towards her ass, and the juicy line that formed from her pussy to her panties had just separated. I knew this was going to be the most magnificent meal I've ever eaten, and she was into it.

Her hand rubbed the top of my head and as soon as my tongue and her lips made contact, she moaned. But when my tongue parted her lips and hit her pink pussy and the hole inside, she let out a cry that surprised me but spurred me on.

"Aaaiiiiieeeee ooooooooooohhhhhh MY GAWWWWDDD! OH YES! Lick my pussy John!"

It was sincere, but bordered on over the top at first. I at first thought she watched one too many porn movies and was acting, but I quickly realized the girl with the shy voice was one wild screamer while getting tongue lashed in her pussy. Her pussy was sweet but tasted like pussy. Pussy is one of those tastes that is indescribable. Sweaty, sweet, musky- it doesn't "taste like chicken" unless she recently fucked a chicken. But the person who can make a beer or soda or cracker that tastes just like pussy and then sell it will be the greatest person ever.

I lapped at her lips and hole, occasionally flicking her clit, and driving a finger inside. I mixed it all up, and if the first thing I knew was how aroused she was, and how good and pure she tasted, the other thing I was aware of was how tight she was.

"Oh my, oh my, let me cum, John! Let me CUUUUUMMMMMMMM! AAAAIIIEEAAAAA! OOOOHHHHHH OOOOHHHH! YESSSS! YESSSS!"

She came and almost spasmed off the island. I quickly grabbed her and held her close to me. My cock had leaked through my satin boxers and smeared against her leg. "Lead me to your bed and we will take care of that," she gasped.

I took her hand and she wobbly walked to my bed. The skirt, bra snd panties all came off, leaving only the stockings. I took the remainder of my clothes off and reached into my top drawer and realized I had made a rookie mistake. I had 4 condoms left in a box of 12, but they weren't the freshest.

But we should be fine. Right?

I held the condoms up and she slightly nodded. I walked over to the bed, my stiff cock pointing up to the sky. She took it and stroked it, rubbing the precum over the tip, and licking her fingers.

"Mmm," she said. "Maybe I will have to suck it later, but right now, I want to feel you fill me up."

I tore open a package, taking the round disk out. I placed the reservoir tip on the end of my cock and started to unroll, but there was a lot of friction and resistance. Maybe it was because they were old, maybe it was because I was more horned up than I think I ever had been, but whatever the reason...

The condom tore, poking my cock out the end.

Shit! One down, three left.

Number Two successfully rolled down my shaft, the clear yellow hue to the condom made my cock look like a bronze phallus. No, a Golden Phallus. Powerful, like Zeus.

As she lie down, her hair covering my pillow, she had her knees bent and spread her legs apart. Her breasts were still slightly flush and her nipples were still rock hard. They rose and fell with her breathing. She smiled at me and her eyes invited me to join her so I did. I climbed on top of her, pressing my chest next to hers, feeling her breasts against me. I could tell our midsections were close to being lined up while we kissed until she said, "I'm ready. Take me, John."

I sat up a bit and widened her knees out, and then I took my cock and placed it at the entrance to her opening. I pushed slightly, watching her lips grip me, feeling some resistance. Then my head disappeared inside her, and she gasped out a moan. She was tight, real tight, but I slowly made my way in, and as I sank my whole length into her and stopped, she finally remembered to breath.

"Ooooh, ahhh, sooooooo deep," she said.

"Are you okay?" I asked.

"God yes! Now that we know it fits, use it. Make me scream."

I slid back and pushed back in faster.

"AAAAHHHHHEEEEEEEEE!"

Slide back out, pushed in faster this time.

"Aaaaahhhhheeeeeiiiiiiiia. Yes!"

Out. In. Deeper. Faster.

"Eeeeeeiiii! Ahhhhhhhh! Eeeeeeiiiii! Yes! Yes! Aaaaahhhhhh!"

Each thrust caused her to exhale and scream. It wasn't fake or contrived, it was real. She enjoyed it and I did my best for her. I felt her pussy clamp down before she said, "Don't...stop...cum...cumming... oh...oh...aaaahhhhh-AAAAAAHHHHHHEEEEEEEIIIIIIIOOOOO GAAAWWWWD! YES!" She came hard. Her eyes rolled back into her head and she froze, almost like she was having a seizure.

And now I was there 3, 4 thrusts maybe and I would be done. Her pussy was having spasms and I wanted to be sure it was still okay to cum inside her, condom or not. "Ugh, ugh, gonna...cum...inside? Or...pull...out?"

She couldn't answer, and then it was too late. I came hard. Rope after rope shot up the hose inside my cock, only to be met with resistance by the condom. It had held!

I came down from my cumming high and rolled off Claire. She was starting to turn purple and I kissed her and rubbed her clit, snapping her out of it. With a long bresth, she said, "Wow. Is it always this powerful?"

Remembering what Meg had told me, I replied, "Were your other times not like this?"

She looked at me, then looked away, and rolled away. I spooned up behing her, sticky condom still on, pressed between her ass cheeks. "I have, uh, never actually had a guy inside me...like that," she said. "I've licked on and gave a few handjobs on car rides, but as far as MY pleasure goes, I've never been treated like you just treated me. Meg told me you were gentle and she taught you how to treat a woman, and she helped me...break...I guess she took my cherry so I wouldn't be embarrassed my first time."

She seemed embarrassed by this revelation. I had a pretty good idea about this ready, but I wanted her to feel good about what had just happened. I hugged her tighter.

"I'm embarrassed and...hope you still respect me. Sorry I lied. I wanted you to treat me good my first time, but now I feel...ashamed."

Shit. Now what? I hate post-coital talk, and now I needed to be a shrink when all I wanted to do was rest so we could go again.

"Claire, did you enjoy it? Was it fun?"

She rolled over so she could look me in the eyes. "Yes. I loved it. Did you?"

"Of course. You were great. I love feeling you," I said.

"Did I...disappoint?"

"Of course not. I was a little worried when you stopped breathing, but you are a fantastic lover, and I have really enjoyed our time together. But I definitely loved this also."

I was leery about using the word "love" too much because I didn't want to have to lie and say that I loved her...right now. I definitely liked her and felt strongly about her, but I did think we were at the romantic love stage yet.

She rolled over and pinned me down, causing my cock to respond. "Oh, you loved THIS, huh? What makes you think you will ever get inside again?" As she was pinning my shoulders down, she wiggled her bottom at me, lining my cock up.

"Do you think we need another condom, or should I see if this one will hold again?" Claire asked.

I maneuvered around, poking my now hard cock that still had my soiled condom on, up her pussy. I thrust up a few times, filling her again.

"Eeeeeiiiii, ooooohhhhhh..." she screamed.

I knew we should not use the same condom again, but we did. She rode me, figuring out what angle suited her best. I knew it was wrong, and I now realize what that little snap was, but when I came this time, she felt my spunk fill her and two huge loads of cum flooded out of her pussy, down my shaft, onto my balls and pooled around my ass.

"Oh, shit! Sorry Claire," was all I could think to say.

"It's okay, I am on the pill," she said.

We dozed off for a while, and then did it again. 5 times total that night. After the condom broke we stopped using them and I filled her up over and over again. She said she loved me. I said I did, too.

I knew I was in trouble.

******************************

We stayed in bed most of Sunday. By Sunday night I took her home and when Claire went down the hall to the restroom, Meg said, "We need to talk. When are you done with class tomorrow?"

"Noon," I said.

"I'll come by. Don't say anything."

Claire came back in, looked at me, then Meg, and back to me. She knew something was in the air, but neither Claire nor I knew what to make of it. Then it was time for me to leave, so I hugged Meg and kissed Claire.

Noon Monday showed up, and I had sense of dread. Meg cam over, looking great. Womanly. Confident. Sexy.

Damn. I loved fucking Claire, but my heart really belonged to Meg. Long legs, short skirt, no bra underneath her blouse, I was in trouble.

So I stalled and tried to delay what I hoped was inevitable, but also didn't want to happen. "So, did you get dick, pussy, or both?" I asked.

"I crashed at the house and no one even fingered me," she said. "Now I feel like I am missing out. And I realized something."

"Oh, yes? And what is the nature of this epiphany?" I asked.

"Love. Listening to Claire talk about fucking you, and all the tricks I taught you that you then showed Claire, I was jealous. Jealous. And upset. What have I been doing? You are right in front of me, and I have been shoving you away, and steered another into your arms, and you into her. And that made me jealous."

I was stunned. I just had 36 hours of fantastic sex with a woman that would do anything for me, but the one I really loved, who had been pushing me away, now professed her love to me.

"Okay," was the best I could say to break the silence. "Where do you want to go from here?"

"Make love to me, then decide," and then she took her top off, and dropped her skirt.