Follow up on my encounter with [m]y best [f]riend

A while ago I wrote about my nearly busted encounter with one of my best friends, Anne (name obviously changed). Many of you commented (thanks!) with positive reinforcement, and many of you also wanted more. Well…there is more, and I’ve finally gotten around to writing about it. I welcome any and all feedback, and if you all really like this, I might write more ;-) For those of you who want the visual reference, I’m about 6’2”, 215 pounds, with brown hair and eyes. I’m not huge, but my 7½” inches never seems to disappoint. Anne is about 5’4”, with the body of a soccer player…flat belly, with muscular legs and a bubble butt, with brown hair and blue-grey eyes.

After our first encounter, Anne sorta freaked out. She claimed that we were better off friends…something about how she always ruins relationships and she valued me too much as a friend, yadda yadda. We stayed very close though, and always had deep intellectual conversations. Ironically, while I was very physically attracted to her, I was even more attracted to her mentally. But I digress. About a year after our first encounter, Anne got accepted into a graduate program on the west coast (we’re both originally from the east coast). After much thought and deliberation, she packed up and moved across the country. Obviously I was devastated, but we managed to keep in touch between texting and skype. I could tell she was homesick, and eventually she asked me if I wanted to come and visit. Of course I took her up on the offer, and it just so happened that our spring breaks coincided, so I booked my plane tickets out west. We’re both avid skiiers, and we were looking forward to west coast skiing (trust me, if you haven’t skied out west, its worth the trip!)

Anne greeted me at the airport with a huge hug and a kiss on the cheek. It was late at night and I had been travelling all day, so after a quick mandatory In-N-Out stop, we made it back to her place. I was a little disappointed to see an air mattress on the floor for me, but I barely laid down before I was fast asleep.

The next morning we made an early start to a ski resort and made it by noon. We immediately hit the slopes and had a blast. As the sun was beginning to set, we decided it was time for some dinner rest. We made it to the hotel and ordered in Chinese. After eating, we both decided that we needed to shower. I went first, and when I was done, Anne went in.

“Fuck its hot in this tiny bathroom,” I heard her say as she opened the door. I turned to look and saw her emerge in athletic shorts and a bra. “I hope you don’t mind…I was so cold earlier, but now I’m burning”

“Uhhh nope. I don’t mind one bit,” I managed to stammer. I couldn’t help but look at her tits.

“You act like you’ve never seen them before,” she said coyly. “Let’s watch TV,” she said, joining me on the king sized bed.

It wasn’t long before she had edged her way closer to me, and taking a hint, I moved to wrap my arm around her. I felt her warm breath on my neck and I felt myself starting to get hard.

“You know I do like you right? You’re like the perfect guy, and you treat me amazingly. I just…you’re too good of a friend, and I know if we dated I’d fuck it up. I’d never forgive myself if I fucked this up and it ruined our friendship,” she whispered.

“I understand,” I said, disappointed. I was hoping for something different, but it seems my hopes were dashed.

“You know I’m still a virgin, right?”

“I mean, I guess I figured that,” I replied.

“I was going to save myself for marriage…but honestly I don’t know that I want to get married. But if I’m saving myself for marriage and I don’t get married, then I’ll die a virgin,” she said.

“Well, yeah, that’s the logical conclusion,” I answered

“Yeah, well, I don’t want to die a virgin. But I don’t want my first time to be meaningless either. I want it to be with someone I love.”

“What are you getting at?” I asked. I immediately realized it was a dumb question, but she didn’t seem to mind.

“Well…you’re an amazing guy, and, well, I love you. We can’t date, I just couldn’t do distance…but I’d love for you to be my first. I trust you,” she was barely whispering now.

Good stuff starts here

I didn’t know what to say in response, so instead I just kissed her. She leaned in to the kiss. I knew there was no going back. Before long, I was kissing her everywhere. First her ear, then down her neck and back up the other side, before making my way down to her collarbone. She arched her back and I took the hint and reached behind and unclasped her bra, allowing her modest C cup breasts to fall out. I immediately went to her left nipple and began to lick and suck on it.

“Wow. You could do that all day…I wouldn’t mind one bit,” she breathed.

I alternated between licking and sucking each breast while playing with the other one, occasionally moving up to kiss her lips. I then made my way down her stomach, kissing and licking all the way to the top of her shorts.

“You know, its hard to have sex with pants on,” again immediately realizing how dumb that must have sounded.

“Well, Mr. Know-it-all, the same goes for you,” she said, as she grabbed my cock through my shorts.

Before I knew it we were both down to just underwear. There was an obvious wet spot on her grey Victoria’s Secret panties. I took the hint and started rubbing her through her panties. She broke the ice and allowed her hand to slip under my boxers, and started exploring my cock and balls.

“You’re sure about this?” I asked, figuring I’d give her one last chance to back out.

“I’m even more sure now than before. God I want you so badly,” she said, stroking my cock. “I want to blow you first though.”

Surprised at how forward she was about it, I slipped off my boxers. She immediately had my cock in her mouth and was expertly sucking me off.

“Wait, stop…” I said, after a few minutes of her sucking

“What? I’m sorry, was that not good?” she said, with a sad look on her face.

“No…the opposite. I’m going to explode if you keep going. Save some for the real thing! Let me return the favor,” I said.

Now, if you’ve read my previous story, you’ll know we had gotten to this point once before when Anne’s roommate interrupted us. I had never gotten to actually see Anne’s pussy and my heart was nearly skipping beats as she slow slid off her panties to reveal a beautifully trimmed bush and tight, wet pussy. It had been a long time since I’d been with a virgin, and I could immediately tell that Anne wasn’t lying.

Anne was on her back and I was on my stomach between her legs. I started by gently stroking the inside of her thighs and move my way upwards, stroking her outer lips gently. She started to moan as I slid my finger up and down her slit, before sliding on finger in, causing her to arch her back with pleasure. At this point I also realized sex would be a challenge. She was literally so tight that I wasn’t even sure she could handle two fingers, let alone my cock. I slowly started moving my finger in and out before sliding my middle finger in as well. She let out a moan, but didn’t seem to object. Sensing that she was liking what I was doing, I started licking her clit as I slid my fingers in and out.

“Wow that feels amazing,” she whispered. I kept going.

I took my fingers out and gave her pussy the full attention of my tongue. Now, not to brag here, but while I might be average when it comes to actual sexual intercourse, apparently I’m pretty good at oral, and have made more girls climax that way than by actual intercourse. I was determined that I was going to make Anne orgasm, so I was working my best magic on her pussy. I alternated between licking her outer lips, to sucking her clit, to licking her clit, while occasionally stroking her pussy with my fingers. It wasn’t long before the little moans got louder and quicker.

“I think…I think I’m…” she couldn’t even get the full thought out before I felt her pussy get much wetter instantly, while at the same times her back arched and she grabbed my hair.

“Holy shit…fuck…ughhh yeah….yeah….oh God!” I knew I had her where I wanted her. “God, Alex, fuck me!”

I got up from my position on my stomach and aligned myself with her pussy. My earlier fears about her being too tight were only somewhat accurate. In her orgasmic state, she was so wet it didn’t seem to matter. Nonetheless I could still feel her pussy like a vice grip on my cock. Anne seemed to be in an odd medium between pain from my big cock inside her and pleasure. I started slow but quickly found my pace increasing. After a few moments inside her I was thrusting my entire 7½” inside her hard. I knew I was on the verge of cumming, but I hadn’t even asked her about a condom.

“Fuck, what do you want me to do?” I asked

“What…do…you…mean?” she replied between thrusts.

“I forgot to put on a condom, do you want me to pull out?”

“Its okay. I want the full experience. I want to feel your cum inside me,” she replied.

Luckily the thought of forgetting a condom actually bought me a little more time, so I used the opportunity to change positions. I pulled out and grabbed her legs, pulling her to the edge of the hotel bed. I grabbed a pillow.

“Put this under your hips,” I said

She initially seemed confused but she lifted her hips and let me slide a pillow under them. I was now standing and she was on the edge of the bed, and the pillow had lifted her hips to the almost perfect height so that I could maximize my thrusts. Now I was fucking her hard, and playing with her nipples at the same time. She seemed to enjoy the little bit of pain of me twisting and pulling on them, so I kept going

“Oh God…shit…is it possible to cum twice? Because I think I’m going to…” she moaned.

Before I could answer I could feel her pussy tighten down and her back arched again. I knew round two was happeneing, and by now I was back to almost exploding myself. I started banging her so hard that the bed was knocking into the wall, I’m sure disturbing the neighbors.

“Yes…yes…YES!!! Oh FUCK!” she screamed, digging her nails into my back. “Harder!”

“I’m cumming baby,” I said, stating the obvious. With a few more hard thrusts I was shooting ropes of cum into her pussy.

I continued fucking her until I was out of cum. I pulled out and she just laid on her back.

“I don’t think I can move yet….that…was amazing,” she whispered.

Anne and I spent the rest of the trip having a blast. We fucked again that night, and multiple times a day for the rest of the week. By the time I boarded my flight back home, I was exhausted and my dick was sore. I don’t think there was a time before or a time since that I’ve had so much sex in one week. If there’s interest, I could be convinced to tell some of those stories too.

Sorry for the length. I hope you all enjoyed the read. Again, I’m always open to comments or other messages via pm ;-)

Source: reddit.com/r/gonewildstories/comments/334i3p/follow_up_on_my_encounter_with_my_best_friend