tagFirst TimeMy First Time

My First Time

bybustylibrarian©

This is not going to sound like a true story. But I promise you, PROMISE YOU, it is.

I don't remember what day of the week it was... but I had talked to my best friend that morning on the phone. It was the end of my sophomore year of college, and she had been my best friend since we were 13 years old. We'd been through as many trials and tribulations as one could image over the last 6-and-a-half-years... and we were closer than sisters.

She was pregnant. She had come to me the previous Fall, one emotional night when she told me she was pregnant, she wasn't sure what she wanted to do about it. She ended up deciding to marry the father, and have the baby. She was going to a college that was about four hours away, so we talked often, but saw each other rarely.

She said "I can't believe I'm going to have a baby in two weeks, and you haven't even had sex yet! I thought you'd be the first one to lose your virginity, and you're the last!" We had been thick as thieves with 2 others girls in high school, and though we had all gone separate ways, we stayed in touch. And the one we dubbed The Nun, because she was so prudish, had been the first to give it up - go figure.

To be clear, our definition of "virgin" meant that we hadn't let a guy stick his dick inside our twat. Oral Sex? Still a virgin. Hand jobs? Still a virgin. Dry humping until you orgasm? Still a virgin. Using the jets in a hot tub to cum? Creative, but still a virgin.

Anyway...

I went out that night with a couple of girls to a bar in town. (Yes, I was under-age, but one of my friends knew the bouncer at the bar, and he let me in anyway.) We met two guys there - Al and Lance. The bar wasn't really popping that night, and we were bored. The guys invited us to a party at their friends' house, and so we decided to go.

The party was pretty fun, and much more relaxed than the bar. We all hung out and had a few drinks, danced around, etc. After a little while, Lance asked Al and I if we wanted to get high... and we did. He only had a single joint, so he asked if we could go for a drive, since he really didn't have enough for everyone at the party. I knew my friends wouldn't want to smoke pot, and they were making a move to leave anyway. I told them I was sure Al would drop me off later.

I left the party with Al and Lance. We drove a little out of town, and parked on a dirt road, so we would be out of the way and hopefully go undetected. Al drove a deluxe van, the kind that the backseat cranks down and converts into a bed. So we cranked it down, took our shoes off and sat on it, crossed-legged, in a little triangle, and passed the joint around. It didn't take long for us to finish it, or to start to feel the effects.

Lance was a mellow, quiet, easygoing guy. Al was a little more intense, and a little more handsome. Lance said something not even particularly funny, and I started giggling. He cupped my knee a little in his hand and said "Yeah, that was some good weed..." and then he just left his hand on my knee. I didn't mind.

But then Al leaned over and said "I want to kiss you."

And then he did.

While Lance had his hand on my knee.

I was pretty relaxed after the pot and the drinks, and it didn't seem odd at all. So, as I kissed Al, Lance began to stroke my thigh. It felt really good. While I kissed Al, I put my hand on the back of Lance's neck, and began stroking it. Being young guys, they were out of their shirts before the next breath. So I stroked Lance's chest and kissed him, while Al removed my shirt. And as I stroked Al's chest and kissed him, Lance slid me out of my pants.

They didn't seem at all interested in each other, so all of their attentions were focused on me. And none of us were in any hurry... we slowly and lazily explored each others' bodies, and continued to undress.

As soon as my bra was off, Lance was on my breasts, kissing and licking them, while I stroked Al thought his briefs. Then, as he kissed me, I removed Lance's pants, and stoked his hard cock. Al moved from my mouth to my breasts, while Lance slipped off my panties, and began kissing and stroking my legs, slowly working up from my ankles towards my upper thighs. Al concentrated on my breasts and mouth.

Then Lance reached the top of my inner thighs, and slowly began to lick my lower lips. At the same time, Al devoured my mouth with his - I had both their tongues in me at the same time and it was divine. It was all I could do to stroke each guys' face as he kissed and licked his nearest slit.

I felt like a love goddess, being worshipped... and it felt completely natural. My whole body tingled with arousal. Their hands roamed slowly over me - up and down my legs, up and down my arms, in my hair, rubbing my breasts, stroking my stomach. While Al kissed my mouth and worked my nipples with his hands, Lance used his tongue and fingers on my lower half. They had me blissed out in no time at all. It was incredible. Lance's tongue thrust inside me. My back arched as Al grazed my nipples with his teeth, and Lance's fingers worked me into a quaking, shuddering breathless puddle.

"Ooh, Ooohhh, Ooohhh" I moaned into Al's mouth, as he kissed me through my orgasm.

I came with Lance's mouth on my pussy and Al's tongue in my mouth.

Undoubtedly relaxed by the pot, neither was in a hurry to stop, even though I was quite satiated. I had to sit up and physically remove myself from each of them to get them to stop... looking back, I probably should have just let them continue their actions for as long as possible. But, feeling so loved-on and euphoric, I wanted them to feel as good as I did, and I knew it was their turn.

Having never been in the situation before, I didn't really understand the protocol... but since Al's cock was near my face and Lance was within arms-reach, I went with it. Neither guy seemed to mind. Looking from one to another (as best I could) they both had their eyes closed, and appeared pretty happy about the situation. I was sucking Al off, as I was giving Lance a hand job.

It had been a pretty erotic encounter up until now, so it didn't take very long for either of them to climax. As I had Al's cock inside my mouth, Lance's hips began to jerk. I let him cum on my chest. And I think the sight of that was all Al needed, as his hips began to jerk, I sat back and let him cum on my chest, too. Afterwards, we lay in a heap of naked limbs, and bodily fluids. If it were to happen today, I would be looking for napkins or paper towels, and worried about cleaning us all up. As it was, I didn't care much about anything at the time.

Eventually, one of us was thirsty, or had to pee... either way, we disentangled ourselves, wiped ourselves off a bit with Al's tshirt, slowly got at-least-partially-dressed, and decided to drive back to civilization.

Lance was first... Al dropped him at his car, and he quietly said to me, "See you later," and exited the van. I was pretty sure I would never see him again, and it turned out I was right.

As Al and I drove back to where my car was parked, we stopped at a red light. He looked over at me and said "I just want to kiss you some more..."

Although I was pretty sure he meant more than kiss, I wasn't ready to end the night either. I said "Okay..." a smile quickly spread across his face, and instead of going straight, which would have taken us back to my car, he turned right.

We drove up over the hill, and pulled off onto another dirt road. He put the parking brake on, left he radio on, and we retreated to the cranked-down-to-a-bed-backseat... As I was currently lounging in just my panties and a tee-shirt, I wasn't too far from naked. Al had been driving in his pants, but without shoes or a shirt, so as we lay on the bed in the back, kissing... it didn't take very long before we were both completely naked again, kissing and rubbing against each other.

He was, in fact, laying on top of me. Kissing me. Trying to part my thighs with his knee.

I, being the experienced tease that I was, knew exactly how to handle this awkward situation.

"Oh, well, we can't, You Know... because, well, I'm Still A Virgin."

He stopped kissing me, and stopped gyrating on top me. He looked straight into my eyes and said, "Ok. That's cool. But... How long are you going to be like that?"

First, to his eternal credit... he stopped. And even though I said I was a virgin, I had NOT acted in any way would make him think that, up until to this point. So, the fact he even considered my words earned him huge points in my book.

Next, I thought... he has a point. How long AM I planning to be this way? I had been on birth control pills for over 3 years, because I kept thinking it was GOING to happen... And, honestly, it should have happened before now... I had given and received many many hand-jobs, as well as oral sex, and I was a hormonal time-bomb. And since I was still a little high, and still a little buzzed, and still euphoric in my post-orgasmic state from our back-seat-three-way-fun earlier, I thought to myself, "He's right! Why not? This seems as good as time as any, and he's been pretty skilled so far, so..."

All of that flashed through my head in the matter of a few seconds, while we continued to kiss. So I broke away from him and said "Al?"

"Yes?"

"Do you have any condoms?"

"Yes..."

"Then, I think I'm going to be a virgin for about 30 more seconds..."

He smiled and kissed me, then grappled for his pants, where apparently the condoms were waiting.

He grabbed one, sheathed his shaft, and resumed with kissing and rubbing against me.

I was nervous - I mean, everyone's heard stories of how it hurts the first time, and I have always been super wimpy when it comes to physical discomfort. I really didn't know what to expect. Sure, I had dry-humped guys before, so I was familiar with the weight of someone on top of me, as well as the pressure of a hard cock against my sex... and, as I said, I had enjoyed the feeling of a guys fingers against and inside me... but a whole cock inside me? How deep would it go? Would it stretch me out? Would it even fit? Oh my god, what if it didn't fit?

He continued to kiss me, and play with my nipples, and slip his fingers inside me... I might have been a little scared, but I was mostly excited. I was eager to feel him inside me. I had read a lot of romance novels, and my expectations of feeling his "throbbing manhood slide into my wanting core" was something I'd been dying to experience. The anticipation was overwhelming. I literally couldn't wait any more. He asked if I was ready, and I said yes, and then... oooohhh... ouch!

It was such a strange, filling sensation. I was definitely stretched more than I expected, as the head of his cock slowly pushed inside me. And as he slid his shaft in and out, going deeper and deeper each time, the rough sensation of his cock against my inner walls was overwhelming.

It kind-of felt good, but mostly, it didn't. As he pushed inside me again and again, I kept moving my hips in rhythm with his, because THAT part felt good, and to encourage him to keep going. I was this far... I wanted to be able to say I had officially "DONE IT." But as I clenched my teeth and groaned quietly through the burning sensation inside me, I occasionally let a soft "Ow..." escape my lips. As his speed increased, so did the uncomfortable friction. My vocal angst grew more and more audible, until finally...

Thrust.

"Oow."

Thrust.

"Oow."

Thrust.

"OOWWww..."

THRUST! THRUUUSSSSTTT!

"OOWWWwww..."

But then, it was over. And we disengaged, and he kissed me, and he ticked my torso a bit, as we got dressed. Again.

We got back to where my car was parked, and as I gathered my purse, he said "I need your number, so I can call you..."

I wrote it down, and thought the odds were 50/50 on if I saw or spoke to him again.

He called the next morning.

Huh? Okay, well, that was a good sign. He wanted to go out, which I knew meant probably have sex, and since I was still sore from the night before I said no, I had to study, but maybe the next night...?

He said "Okay, well, I'll call you tomorrow."

And I didn't think he would.

But the next day, there he was, on the other line, asking if I had to study again or if I could break away for some fun... I said "All work and no play isn't exactly my motto."

He laughed and asked where I lived, so he could pick me up around eight o'clock, and go to a party. I told him I would meet him there - only because I didn't know his friends, the party was at a house a bit far from campus, and I wanted to have my car, in case I felt like leaving. He understood, gave me the address, and said "I'll see you tonight."

This was going better than I thought it would - after having lost my virginity to a guy I had just met, I didn't have high expectations about any kind of relationship. But he had called me - twice! - and genuinely seemed to want to see me again. (In retrospect, I realize I was a pretty easy lay, and he was probably just thinking that if he called me, I would show up and service him.)

I arrived at the address he'd given me and knocked on the door. A friendly guy answered.

I said "Hi, my friend Al invited me...?"

He said "Sure, come on in... Hey AAALLLL - there's some hottie here for you!"

I giggled as Al bounded up the stairs, drinks in hand, with a huge smile on his face.

"Hey! Good to see you - I'm glad you made it."

I took one of the drinks from him and laughed. 'I said I was coming... "

He grabbed my hand and we walked to the kitchen, grabbed some snacks, and headed outside.

We sat down on the patio furniture. There was no one else around, and he asked, "Did you really have to study last night?"

I was embarrassed, but admitted anyway, "Not really. I was pretty sure you'd want to have sex again, and I was sore."

"Sore?"

"Um, yeah... a lot of girls are sore after their first time."

"That wasn't REALLY your first time, was it? Like, your FIRST first time?"

"Um, yeah. It's not like it was super comfortable..."

"It wasn't? I thought you enjoyed it?"

I chuckled a little. "Oh yeah, I say "OOOWW" whenever something feels good."

He turned 12 shades of tomato.

"Al, it's okay. It was my first time. I knew it was going to hurt..."

"Yeah, okay..."

"I thought I kind of let you know that, with all the times I kept saying 'Ow', right?"

He mumbled something.

"What?" I asked.

"I, well, I thought you were really into it. You know, and calling my name..."

I probably could have played it slightly cooler, but I was so shocked at how completely stupid he sounded, I immediately started laughing. A Lot. I might have snorted a couple of times.

'You... you..." I was breathless and could barely get words out between the laughing "You thought, when I was gritting my teeth and saying "Ow", like "ouch", you thought I was passionately whispering your name, 'Al'... is that right?"

He very, very sheepishly admitted "Yeah... I did."

Oh god. Good thing he was cute, because this boy was NOT smart.

I knew in that instant this would be the last night I saw him. I could blame my decision to let him de-flower me on any number of things...

The amount I had to drink that night.

The amount of weed I had smoked that night.

The fact I was a hormonal bundle of energy that needed to be released.

The teasing my best friend had given me that morning.

The sexy three-way sandwich we'd been involved in just a few minutes prior.

The fact I just wanted to start doing it...

But I could not justify any reason to continue to see this dipshit.

Seriously... he thought I was calling his name? From the first penetration? Maybe HE had read too many romance novels, or had an enormous ego, or was simply stupid, or some combination of factors, but, regardless, I knew this would never last.

After a few shots of liquid courage, he continued. "I mean, it's not like you were acting very much like a virgin..."

I couldn't argue that fact. Fooling around with two guys at the same time wasn't something most women did, let alone women who considered themselves virgins. And, I had been a sexual creature for a few years - so even though I hadn't experienced actual penile penetration before, I walked the walk and talked the talk like someone who was familiar with sexual pleasure and gratification - because I was. Just not THAT... so I really couldn't blame him for not totally believing me.

"Okay, okay, I know... I was not your typical first-timer." I conceded, laughing. He laughed, and then he leaned over and kissed me. He was a pretty decent kisser, and though I never intended to see him again, I was already there, at the party, kissing him... so yeah, we did it again. It still didn't feel great, but it felt pretty good, and the burning sensation was gone, so I figured I would be ready to actually enjoy the next guy, whenever I met him. It turned out, the next guy wasn't even a guy - but that's another story...

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by Anonymous

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by ReefBeach05/16/18

Definitely real

A great story, nice mix of detail & craziness, very authentic sex. I wanted a bit more pregnant friend - she kind of disappeared. But that's a minor thing: 5 stars from me!

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by joelafayette05/14/18

Nice story

I enjoyed it. We don't get enough first time stories told from the woman's perspective. My only point would be I think you can take your time and make the story longer. I'd like more details duringmore...

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by HardXsRHere05/11/18

a real nice way of loosing your cherry

I enjoyed reading your first time. I wish
that I was the third guy smoking some pot
and getting in your panties and popping
your tight cherry. I gave you a big FIVE.

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