That Pesy Virginity

At Eighteen years and three months old my mind only ever focused on two things. Football and sex. Not that I was having any sex. Some of my friends were no longer virgins well they claimed not to be, but word on the around town was that putting my dick into a vagina would solve all my problems.

My best friend Trim and I were in the same boat. All we wanted to do was fuck a girl, but none of the girls we knew wanted to let us anywhere near them. It was a constant topic of conversation between us, and Trim was always imagining ways to simulate sex - he got caught fucking a water melon with a hole carved into it, he spoiled a packet of chicken fillets when he put them in a sandwich bag and tried to fuck them. You name it he tried to put his dick into it. I wasn't nearly as adventures a bottle of hand cream was a far as I went.

One night Trims brother Dave was having a party at his flat and we were going. As the party was winding down some of the guys were sitting in the living room talking about sex. These guys were all in their late twenties. One of them told a story of how he met this girl in a bar and got her home. Only then did she admit that she was on her moons (on her period) and that her pussy was out of action.

She suggested that they try up the "browner." He regaled us on how amazing it was to fuck her ass, claiming that it was much better than pussy, because as he put it, "she can't get pregnant."

So he didn't ned a rubber. He just lubed her up with baby oil and slipped in. Of course all this talking about sex gave the eighteen year old virgins boners and soon Trim and I became the subject of ridicule.

A couple of days later I was over at Trims playing his xbox, when he asked me if I remembered the sex conversation from the party. Of course I did.

Tentatively he said, "You know I have been thinking about what Rod was talking about." I paused the game and looked at him.

"About fucking the girls ass." I blushed and grinned at him. We had been best friends since either of us could remember, but I still got embarrassed talking about sex with him. Even though it's about the only thing we talk about these days.

"Yea, I think we could try it." He offered.

"What! We can't even get a girl to kiss us never mind fuck her in the ass." I stated making him laugh a nervous laugh before bashfully saying.

"No with each other." I was startled by this. Although we talked a lot about sex and we even jerked off in the same room as each other. He made it clear that we would never touch each other because as he put it, "That would be gay." Now here he was suggesting that we fuck each other.

"Sounds a bit gay Trim." O said trying to judge his true feelings. He reluctantly agreed with me and that was that. For a few days.

Terrance Griffith was the local arsehole. He was a bully and a cunt, thankfully no one liked him. But word went round that Terrance had fucked a girl. One day he cornered me as usual and started hurling insults my way. It never normally bothered me but when he rubbed the fact that I was a virgin in my face I exploded. I managed to punch him on the nose, I'm not sure if I broke it but it was bleeding. Unfortunately all that did was give Terrence an excuse to easily kick my ass.

It was the last week of collage before summer, so they let me off with a warning. My mum went ballistic and I got grounded for 2 weeks. When my incarceration was over I met with Trim as usual at his house.

"Lets do it." I almost screamed.

"Do what?" Trim said taken by surprise by my opening gambit.

"I cant have that cunt Terrence rub my nose in the fact that I'm still a virgin. So let's do it so I'm not." I reasoned

Trim looked surprised but he was also wary that he might have the wrong idea. So he wanted me to spell it out. "Bobby, what do you want to do?"

I hesitated a little I didn't want to be the one to say "Please Trim let me fuck you in the ass.", but I wanted so badly to lose this weight hanging around my neck. So I closed my eyes and meekly said, "You know, what you said about what Rod said."

He smiled at last he knew that we were talking about the same thing. But he wanted to make me squirm, I had unintentionally hurt him when I insinuated that it was gay.

"I thought it was a bit gay bobby, now you want my hard on in your ass." His grin was telling, I knew that he was purposefully be a prick.

"You know that's not what I mean, I just cannot live in a world where a fucktard like Terrence Griffith is better than me."

He giggled and said, "That's the spirit." Before turning off the Xbox and turned to face me, I honestly rather that he did as the level of embarrassment rose to excruciating levels.

"So how do we do it then?" he asked. To be honest I hadn't thought about the actual fucking just that I wanted to fuck.

"I don't know, you pull down your pants, I'll put the hand lotion on my dick and you bend over and pull your ass open I suppose."

A startled look shot across his face, and he said, "No way am I going first."

I countered his argument with, "Well It was your idea so it's only fair."

We both consider it for a few moments. Then he had an idea, "Ok I know how we do it so we both cum." I couldn't wrap my head round how we could fuck each other at the same time. We had seen enough porn but it never seemed possible.

"I don't get it?" he smiled and said,

"It's simple, we wank each other off, the first one to cum has to be the girl first!"

And with that two best friends were disrobing. Trim was already hard and I was still flaccid. He put some porn on his Ipad in front of us, and said, "We can look at the porn while we do this. The first one to spurt has to take the other one in his ass. Deal?" He reached out his hand to shake on the agreement. As I extended my own to meet his he moved his hand and give my dick a flick.

"What the fuck dude?" I protested but he just chuckled.

"Well we might as well get the awkwardness out of the way." He said, I think I pouted a little, but he brought a smile back to my face when he said, "What you wanted this to be special?" I chuckled a little and swore at him.

We sat down on the bed beside each other. Seconds turned to minutes and we watched the porno on the ipad, neither of us daring to look at the other, we certainly didn't want to be the first to reach out and take the others cock in hand. Eventually the lesbian porn got me hard, embarrassment followed when it dawned on me that my best mate could (if he was so inclined) see my erect penis. I tried in vain to hide my member, I guess it was force of habit. Trim noticed and broke the silence, "If we are going to do this I suppose we should start."

He reached across my lap and gently touch my cock. My breath escaped me, this was the first time that someone had touched my dick who wasn't cleaning me or trying to cause pain or embarrassment.

He gently rubbed along the underside before wrapping his fingers around my girth and giving me a couple of gentle pumps. He stopped his ministrations and said, "Dude?"

I opened my eyes and realised that I should be doing the same to him. I mumbled an apology, and dutifully reached across and touched his cock. I was amazed with the feeling of it. It was hard yet soft, it felt so different from mine, it was longer but slimmer. He gasped as I began to jerk him, I'm guessing that I was doing some gasping myself.

I was lost in the feeling of his handy work along with the sight of 2 blonde ladies straddling a double ended dildo, I eventually looked up only to see Trim had not looked at the Ipad once, he was fixated on me and my dick. He stretched out a second hand and cupped my balls. A little precum was oozing out of my cock and he stopped fondling my balls, he wiped his finger across my tip taking some of the fluid and put it in his mouth. That was all I needed, two pumps later and I exhaled the words, "Oh no!"

As I shot ropes of cum across the room. It was the most powerful orgasm I have ever had. And as the intensity of it began to subside, the enormity of what it meant began to dawn on me. I was moments away from getting butt fucked.

He gently pumped me a few more times milking the last of my cum out of my swollen member. I was frantically trying to make him cum so that my fate would be in my hands. I looked up from his cock and he was grinning from ear to ear.

"You tasted my cum you queer." He just flicked his hand in my direction and splattered my semen onto my naked chest and face.

"You seemed to like it. Now how do you want to do this?" My eyes widened in horror.

"I don't" I stammered almost in a panic.

"Dude we agreed. Don't be a dick" reluctantly I shook my head in agreement. After all being a dick was worse than being a virgin. I stood up and turned round, and got onto all fours on the bed, offering my best friend my ass for his pleasure. He actually jumped to his feet, raced to his dresser and got the bottle baby oil he liberally poured some onto his hand and tossed the bottle to me. As he lubed up his dick I lubed up my ass.

He approached behind me, I felt his hands on my hips pulling me toward him, this was it.

"Go slow please?" I whispered, he nodded. I felt the tip of his cock push against my body, it felt different than when it was in my hand. There was no softness, just stiffness. It glided about my behind missing its target a few times before he took it in his hand and aimed it. I felt the pressure on my ass at the entrance. Instinctively I closed up, I knew I shouldn't but I couldn't help it.

"Buddy you will need to relax, pull your ass open." I leaned further forward resting my chin an head on the mattress, I reached back and spread my cheeks apart, and the tip of his cock entered me.

The sharp pain made me cry out. "Stop, stop" he did but he didn't withdraw, he held his position and after a few breaths he pushed a little further in. More pain brought tears to my eyes and he paused again. He slowly inched in, pausing each time giving my ass time to adjust.

After a few minutes of this he was all the way in. he rested again with his pelvis tight against my ass cheeks.

"Dude I'm inside you!" he excitedly exclaimed. By now the pain had subsided, and I knew that the worst was over.

"Get it over with then." I sighed. He slowly pulled his cock out, leaving just the tip inside me before he slid back in. this slow motion screwing was almost pleasant. He repeated it a few times, I had to ask him to put more oil on but he was happy to oblige.

As his pace quickened, I experience something new. A stab of intense pleasure as he reached the end of his inward stroke. It was fleeting, but enough to re-engorge my own cock, which was oozing pre cum. By now he was ploughing me.

His nails digging into my hips, holding me in place. Not that I was going anywhere. I was on the verge of Cumming again.

I cried out, "Oh my god!" he stopped.

"Dude you ok?"

"Don't fucking stop!" I urged, three strokes later and my orgasm from only moments earlier, which I described as my most intense ever was dwarfed by this one.

I spewed cum on to trims bed. I roared in ecstasy, my ass involuntarily clamped down on Trims dick making sure it wasn't going anywhere. I fell forward onto my belly dragging him by the cock down on top of me.

The additional tightness around his dick pulled his orgasm out of him, he slammed home one last time and I felt his cum spew into my cavity.

He lay on top of me I could feel his cock still in my ass pulsate the last of his orgasm into my body. I'm not sure I could speak, I know I couldn't move, I was physically and mentally spent.

"Holy shit dude!" Trim said. Before asking, "What was it like?"

He rolled off me, as he did his softening cock plopped out of me. Unplugging the dam of cum, it felt like litres of if seeped out of me.

He said "Well? What was it like?"

I couldn't answer, he marvelled at how wasted I was.

"Fuck I can't wait for my turn." But at that moment I knew my position in life, on my knees with a cock deep in my ass.