Busting Bens Cherry

by AnonymousMan

11 Oct 2006 9554 readers Score 8.5 (90 votes) PDF Mobi ePub Txt


I belong to a fraternity and for fun we had a 'Sex Scavenger Hunt,'

where various acts would earn us points. I'm always up for some good kinky fun and I was looking forward to checking off as many things on the wild list as possible. As soon as I saw that fucking a virgin was on the list, I knew exactly whom I could seduce to fulfill this requirement and get 150 points. There is another gay guy who graduated with me (he was in my homeroom) and I knew for a fact he hadn't messed around with anyone yet. We were friendly toward one another, knew the other was gay, etc. Every so often I send Instant Messages back and forth with him online. Sometimes I get a little frisky and try to get him to submit to me and let me take his cherry. No luck. So far.

His name is Ben and he's just as cute as one can be. He was one of the 'drama geeks' in high school but he really grew into his looks during our last year in school. He is tall and lanky with big brown eyes and a head full of soft brown curly hair. Every time I see him in person I just want to run my fingers through those curls.

I know where Ben was working so I dressed in a very loose pair of nylon running shorts and a baggy tank top that showed off my arms, back and even my nips. The place Ben works is an ice cream place. I had a plan. I jogged down to the ice cream place and really worked up a sweat. Ben was working with two younger girls who giggled nonstop at me as I made small talk with him. As luck would have it, he only had 10 minutes left in his shift before he could leave. I ordered a jumbo chocolate cone and said I was going to sit at a picnic table outside and wait for him. I told him when he was done to come find me, that I wanted to ask him something. I took my cone and resisted the urge to reach through the little window and stroke that hair.

I gave my cone slow licks, making sure I didn't eat too much of it before Ben showed up. It was part of my plan. It took him awhile, but he finally showed up. I had spent most of that time trying to keep the ice cream from running down my hands and arms. He sat down and I put my plan into motion. I pushed the bottom scoop of the ice cream with my tongue and let it fall off the cone.

'Fuck!' I yelled. It had worked perfectly, leaving a huge brown spot in the center of my tank top. I tossed the remainder of the cone on the ground and made sure Ben was watching. I peeled off my stained tank top and let him get a good look at my naked upper body.

I flexed my pecs and smiled. I leaned back on the table and turned my face to Ben. He was looking at me like I was some kind of centerfold in a porn magazine. 'I shouldn't have eaten that ice cream.

Now I'm sick to my stomach and won't be able to run home.'

'That sucks,' was all Ben said, his eyes sliding from my chest, to my arms to my belly.

I spread my legs a little and put my hand on my shorts, giving my dick a subtle rub. 'Don't suppose you can give me a lift home?' I asked, staring right into his sexy brown eyes. God, I wanted this virgin, points or no points.

'Sure. No problem.' He looked away, embarrassed to have been caught ogling me.

'Thanks.' I turned around to face him. 'I need to grab a shower, but maybe we can go see a movie if you aren't doing anything.

I am bored shitless and need something to do tonight.'

Ben nodded. 'Whatever.'

We walked to his car and he drove back to my place. My mom (she's divorced) wouldn't be home for at least two hours. That was plenty of time to bust Ben's cherry. I invited him in and let him play a video game in my room while I went into the bathroom to shower. I left the door open. As soon as I was finished, I yelled out to him.

'Hey Ben! Could you grab me a towel, bud? I fucking forgot to bring one in with me.' This was a lie. There was a whole closet full of clean towels. I told Ben to grab one from the hall closet and made sure I had pushed back the shower curtain before he walked into the bathroom. He nearly fell backwards and landed on the toilet.

I made sure he got a good look at me naked. I grabbed the towel from him and slowly began to towel off, shutting the bathroom door.

'Sorry, there's a draft,' I said. Another lie. It felt about 100 degrees in the small bathroom. I wanted Ben to watch me toweling off with no means of escape. I pointed at the empty shower.

'Why don't you grab one dude, before we head out? No offense but you smell like fried onions.' He didn't really, but I wanted him in the shower. He took the bait. Sort of.

'Why don't I run home and shower and change?' He stood up and reached for the door.

'Just use mine. I have tons of shit you can wear.' I walked over to the door and opened it, loosely wrapping the towel around my naked waist. 'I'll grab you a towel and I'll wait in my room.' Luckily Ben took the bait. After I got him a clean towel, it was nearly five minutes before the shower was running again. I didn't bother to get dressed. I walked down to my mom's bathroom and flushed her toilet.

Sure enough, five seconds later I heard a yelp from Ben. I went running back to my bathroom. 'What the fuck's the matter man?'

'Nothing. Water just got really hot all of a sudden. It's back to normal now. I'll be out in a minute,' he said.

I walked over to the closed shower curtain and pulled the end back.

Damn, Ben had one hell of a sexy bubble butt. Nice and white, defined by tan lines all around. I looked at him for a few seconds and then saw his hard on. Damn! 'You sure you're okay?'

Ben jumped at my voice and nearly slipped on the wet tub floor.

One of his hands dropped the soap and rush to cover his boner, which was too big to hide behind his large bony hands. 'What are you doing?'

'Just looking at your fine cock. Jesus, let me see that thing!'

I knew he wouldn't invite me in to share the shower so I just climbed in, sinking to my knees so my eyes were level with that big beautiful dick.

My mouth was already watering.

'Man we can't be doing this,' Ben said, his voice an octave higher than normal. 'Someone will catch us.' His body was almost totally smooth, save for a small wedge of brown pubes and some nice armpit hair.

His beautiful curls were matted down and sticking to his forehead and the sides of his face.

'Catch us doing this?' I asked, sliding between his legs and swallowing half his cock.

Ben moaned and grabbed my shoulders, telling me to stop. Then he moaned again and told me not to stop. 'That feels so good!'

I pulled my mouth off his cock long enough to say, 'See what you've been missing?' I sucked him off for a few minutes and felt him erupt in my mouth. His dick didn't loose any of its stiffness. I spun him around and told him to put both hands against the far side of the shower wall. I pried open that hot bubble butt and nearly wept when I saw how pretty his smooth pink (virgin) hole was. I worked it with my tongue for a bit, and then gave him a finger once he was good and ready for it. He was going crazy and I knew he was going to be a hot fuck.

I stood up and wrapped my arms around Ben's naked, wet upper body, tipping his head back so we could kiss. When our lips broke apart I said, 'We need to get out of the shower and go into my room. You need to be fucked and I don't want to risk getting hurt by doing you in the shower.'

He looked at me strangely for a minute and then, without speaking, kissed me again.

Ben and I dried each other off, somewhat, and dove into my bed half wet. I wrestled him onto his belly and stroked his smooth back, watching as his ass reared up like a horny cat. 'We need to do this first,'

I told him, reaching into my bedside table for a rubber and my big bottle of jackoff lube. Ben watched as I rubbered up and greased up my hard dick. I pumped a couple good squirts of the lube on his pretty pink hole and massaged it inside.

He turned his face to me, his brown eyes looking so sexy and his curls - half damp - still clinging around his head. I nearly came before I even put myself inside him. 'Are you going to fuck me?' he asked, his voice a mix of trust and nervousness. I could feel his heart pounding and I kissed his back and shoulders. I just smiled.

I put the tip of my greased cock against his virgin hole. It barely stretched. I pushed a little harder and felt the ring of muscle start to part and let me inside. Ben was moaning and taking extra deep breaths. I caressed his bare skin and coaxed him into relaxing, feeling my dick sink deeper into his cherry slot and his ass muscles flutter around my shaft. I pushed at least half my dick into him and heard a loud gasp. Deeper I went.

'Don't put too much in me, please,' he begged, moaning the whole time.

I leaned forward and wrapped my arms around his chest. I placed a kiss on his right ear and gave him a little lick. 'It's all the way in, dude.'

We began to fuck. I took it easy since it was Ben's first time, but he was able to relax surprisingly fast; within ten minutes I was already thrusting - slowly, but deeply - in and out of his hole. It took all my concentration not to pop and Ben seemed to be growing closer to some sort of big climax. Either that or he really knew how to get into being a good bottom!

With my dick still inside him, I turned him onto his back, putting his legs over my shoulders so I could lean in and deep kiss him while I pounded his tight hole. His ass was going to make me cum. I felt it tighten like a fist around my dick and suddenly Ben's dick was squirting like a broken pipe. His eyes grew like saucers as he realized what a mess he was making. I was probably the first guy who had ever seen him cum. It was hot watching him cum so hard, but Ben seemed almost embarrassed by it.

'Watch me,' I said, sliding out and pulling off my rubber. My dick didn't do anything for a minute. Then it began to unload with as much force - or more - as Ben's had, soaking him even more with hot cum. I was so drained by the time my balls were empty that I collapsed on top of Ben. We were both a mess, a thick layer of our cum between our bodies. I was about to make a naughty remark but Ben beat me to it with his own dirty thoughts.

'Looks like we need to take another shower.' I gave his ass a playful snap as he headed back to the bathroom. I would join him in a minute, but I wanted to put a check next to the 'virgin' item on my scavenger hunt list.