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My Best Friend's Girl

General Sex Stories (Written By MEN)

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Old 12-05-2011, 12:45 PM   #1
Horny Member
Join Date: Dec 2011
Location: North Jersey
Age: 31
Gender: Male
Posts: 15
Default My Best Friend's Girl

If you read the title, and immediately started singing the "hit" song by The Cars, then this story is for you.

I used to think my situation was unique, but forums like this as well as personal experience have taught me otherwise. It seems alot of guys fantasize about (and some actually do) fuck their best friends girl. We never had sex, not yet at least, but that wasn't for lack of me trying! I did manage to score some of the best handjobs of my life out of her though...

She's no longer with my "best friend" (nor is he my best friend really) though neither has to do with our messing around at all. She's actually engaged to another friend of mine now, though I met him through her, so I don't feel guilty about still trying to finish what we've started. It will happen, I'm sure... just a matter of time. We've both admitted it will go down before she's married and I'm engaged (which will be soon!)

Either way - here's just one experience of many with her that have consistently ranked with the hottest sexual experiences in my life - and we never even had sex! Probably part of the intrigue...

We'll call her Hillary. She's about 5'4", a few inches shorter than me, with an average body type. You can tell she was a tom boy growing up, but that hasn't diminished her sexuality in my eyes. She has two beautifully plump breasts, with the cutest, smallest little pink nipples you've ever seen. Average length brown hair, and a non-descript ass.

Onto the story..

We were at an infamous Jersey Shore rock venue watching our friends' band open for a grammy award winning Reggae band. These hints should be more than enough for anyone who knows us!...

We were pre-gaming in the parking lot in our friends' car. Smoking illicit substances, drinking beers and just listening to music and joking around. Her and I were in the backseat of the car, both newly single, and visibly flirting with the idea of renewing messing around after a few year hiatus. She was scratching my back as I was bullshitting with the crew when the idea came of booking a hotel room. We all had had a few drinks by this point, and the prospect of driving a few hours back home after what was sure to be an epic, intoxicated night, proved enough incentive to announce that I had a credit card, and was willing to book the rooms. Hillary said she'd come with me, innocently enough, and we set out on foot a few blocks down to the hotel.

We went to the desk, booked the rooms, got the keys, and make our way up the elevator without incident. We made it to the room, and explored it's old and tired decor which still managed to maintain a semblance of quaintness. At this point, my mind was racing with possibilities, and how to approach the only subject on my mind.

Through a series of questioning, it was determined, that in spite of having hooked up several hot and steamy times (and quite a few hand jobs), she had actually never seen my cock. I said this was crazy, and had to be rectified. She seemed hesitant at first, but I could tell she was just as anxious. She proceeded with the usual "ooh, I don't know" and "we probably shouldn't" and turned to walk out the door and make our way back to the pre-game festivities.

I grabbed her hips, turned her around until we were face to face, and whispered "But I want to fuck you so bad". That was all it took...

She cooed "Hmmm, sex" and we immediately started making out. We always kiss passionately, and this was no different. Our bodies were entwined and our hands exploring each others' bodies. My internal clock was ticking loudly, as I knew we'd been away for awhile now, and as not to arouse suspicion, we decided to make our way back and continue later. Had I known all these years later we still wouldn't have finished the deed, I would've picked her up in my arms, carried her to the bed, and fucked the shit out of her. But alas...

We made our way to the elevator, and as soon as the doors closed, you'd think the gun went off for the Kentucky Derby. We threw ourselves back into each others' arms, kissing hard. I pushed her against the back wall and started kissing her neck and ears as I reached my hand under her shirt and started squeezing those succulent tits. The elevator dinged when it reached the lobby, and just as the doors opened to a waiting crowd, we separated.

As we got back to the pre-game, our crew none the wiser, we exchanged glances that said "I want to strip you naked and jump your bones right here, right now." We registered each others' looks as we exchanged another that said "Soon."

During the show we managed to sneak off and back outside (convincing the door man we were just smoking a cigarette and getting some fresh air). We made our way to the car and disappeared into the shadows. Now, I always wear a white undershirt tucked into my pants. I don't know why. But as the passion reached a fever pitched, she reached for my cock, and laughed when she ecountered the "boundary.

"You always have so many layers" she quipped as she finally fumbled through the barrier and gripped my rock hard cock in her soft but strong hands. "Hmmm" she cooed again as she squeezed and stroked it. All of the sudden, I heard a noise behind us, and immediately separated from her.

"You're such a nervous nelly" she joked, as it was just a stranger casually walking by, taking no notice of us. I should point out now that within our crew that night, there were a few people who wouldn't hesitate to spread the gossip of us hooking up. And I couldn't have my best friend find out. So hence the sneaking around aspect. Which made it even hotter in my book!

Back in the show, the rest of the night passed without a hitch. We got to the room at the hotel again, and laid down the "drunk girl", our friend on the bed. "Well, there goes that idea" I thought as I had planned all night to fuck her on the bed. This girl was down for the count, and others were partying in the room, so we'd have to make other arrangements.

A faction of the crew dispersed throughout the old hotel to go "ghost hunting". It was more of a "run around the different floors of the empty old hotel while drunk and filming" kind of hunt, but fun nonetheless. And I knew my chance would come.

As they rounded a corner, I grabbed Hillary's ass, gave her a look, and pulled her through a side door into an Employee's Only hallway with a service elevator. We immediately started going at it, making out passionately, and roaming each others' bodies. I lifted her shirt above her head, but not off, and started sucking and kissing her beautiful tits and nibbling her nipples. She loves this, and so do I. She reached her hand into my pants again and started stroking my cock. There was a cot in the corner, but literally right under a huge windown (and fluorescent light) and it just didn't seem right to try and take her right there. Again, had I known what I know now, I would've done it. Or at least went and booked another room in this massive empty hotel!

We stopped and said that they'd be looking for us. We agreed to find them, hang for a bit to seem inconspicuous, then announce our plans to call it a night. We found them and did just that. On the way back to the room, I was worried my chances were dwindling. Past the Employee's Only door was the stairwell, and I decided "Fuck it." I grabbed her by the hand, shoved the door open, and began running up the stairs with her hand in mine. We actually heard the door slam shut, then reopen to the voice of our friends asking if that was us, or a "ghost". Thankfully they left it at that, as we made our way up floor after floor in dizying anticipation.

We finally reached the top. "This is it" I thought, as I pulled her to me to once again kiss and grope each other. I took her shirt completely off this time and began sucking on her tits harder than I had before. She moaned and wiggled in my arms as she undid my belt, and unbuttoned my pants, taking my cock out of my pants this time. Since she was shorter, she was on a stair above me, so we could be eye level, and we just stared into each others' eyes. All the while, she's rubbing my cock against her pussy through her pants. I can feel the wetness down there, and am anxious to pull her pants down and fuck her right there.

The next series of events are blurry in my memory due to the level of passion and excitement, but they went something like this.

I again whispered "I want you so bad" or something to that affect. She replied "I don't think I can do it in here... I mean, it's a dirty stairwell..." I said, or at least think I said (she denies this part) that "We can go anywhere you want then, just name it - the beach?"

But before I knew it she was stroking my cock harder and faster. When I say this girl gives the most amazing hand jobs, it is not an understatement. Usually, besides professional rub and tug joints, no one can jerk me off better than me. That's besides Hillary.

Her rhythm is amazing, her anticipation surreal, and her hands so soft yet so strong, it boggles the mind. I can remember vividly saying to her "You're gonna make me cum if you don't stop" but she only used this as further encouragement to go harder and faster.

She jack hammered my cock while we kissed hard, and I think I remember rationalizing in my head, "well, at least I'll still cum, even if I can't fuck her..." and with that, I let out a monster orgasm as I came all over her hand, her bare stomach and her black yoga pants. I definitely moaned, as did she, because she always enjoyed making me cum. She continued lightly stroking it, milking every last drop, until we both collapsed onto the landing in a heap.

We both lit up cigarettes, and that's when the usual guilt kicked in. We knew each time that it was wrong, but we couldn't help ourselves. There's an undeniable sexual tension that has always been there.

We agreed it was wrong, and that this was it - the end - no more. Needless to say, it wasn't, as we have had several more similar experiences, though they never compared to the overall hotness of this night.

In hind sight, if we don't get to put a period (or exclamation point!) at the end of our sentence, I'll always look to this night with a tinge of nostalgia and regret. She's jerked me off in my pants, on a slide, in my car and on her floor since then. But none compared.

Years later, whenever we talk about it - she admits it wasn't the stairwell's dirtiness so much as 2 other factors that made her fight the urge to fuck me that night.

1) she wasn't expecting to get laid, and therefore hadn't shaved in quite awhile leading up to this night


2) she's admitted that my cock is the biggest she's seen/touched etc. and was actually frightened by it. She thought it would hurt!

I think she's over that now. And if there is a next time, rest assured I don't care if she's shaved, if my cock is too big, if she's on her period (two of the reasons we didn't in two other instances) or if we're in a dirty stairwell.

I will fuck her!

Thanks for reading - sorry it's so long!
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