Jack and I had been friends all the way through high school. We were inseparable, I spent more time at his parents house than I did at my own and our parents got on really well. When he was 15 and got his first girlfriend, I admit I felt a little jealous. We were never “like that” although secretly I sometimes wondered what it would be like if we were.
We ended up applying to the same college and even picking the same subjects. I couldn’t imagine us not sitting together in classes, copying his notes or helping him with his maths.
In the summer holidays we would just hang out at his, playing video games. He got really competitive and hated losing. Sometimes I’d let him win just to keep him happy.
One day we were bored and had nothing to do. His parents were away for the weekend so we had the whole house to ourselves. I knew where his mum stashed her vodka so I dared him to steal some. I didn’t think he’d do it, but he carefully removed the bottle from the cabinet as if she was there and could hear us. He unscrewed the cap and poured out a glass full before adding water to make it look like he hadn’t taken any, then swirled the bottle and put it back.
It was a hot day and I was wearing a pink t-shirt and a pretty little yellow summer skirt. He was in shorts and a pristine white t-shirt. I suggested we play a game. I asked him if he’d ever played truth or dare before, he hadn’t. I told him we would each take turns suggesting a dare to each other and if we didn’t want to do the dare, we could forfeit by having to answer any question the other person could think of honestly.
He was a bit surprised I suggested it, but being the competitive sort and never wanting to pull back from the challenge. I’ll start, I told him. I said he had to take a shot of the vodka he’d just stolen neat. Neither of us drank before but he took a shot glass from the cabinet and poured some of the vodka from the glass to the shot glass, spilling it all over the kitchen worktop as he did it. It picked it up, put it to his nose and recoiled from the smell. “A dare’s a dare” I told him, willing him on. He took one deep breath then gulped down the shot in one go, before complaining of the burning sensation in his throat.
Your turn, I told him. Lacking imagination, he told me to do the same thing. Yet more vodka spilt on the worktop, we wasted more than we drank, I tried to sip it at first but he just demanded that I down it, just like he did. It was not pleasant. I couldn’t understand why people liked this stuff. I started to feel a little warm after the shot, I wasn’t used to it! Am I drunk, I thought to myself.
Next, I asked him to take a spoon of hot curry powder and swallow it. I got out a tea spoon and heaped it high. “This is going to be easy” he said. I placed the spoon in his mouth and he began to cough, the powder went all over his white t-shirt, turning it a browny red colour. He downed a glass of milk, his tongue still burning from the curry powder, spilling milk on his shirt to add to the powder.
He tried to wash it off but that just made it worse. “Mum’s going to kill me” he said. “It’s a new t-shirt”. I just found it hilarious, and offered to help him wash it so his mum would never know.
I told him to take his top off so I could stick it in the wash. It was quite nice seeing his flat chest and a little chest hair between his nipples. I hadn’t really noticed his body before but I had an urge to see how it would feel to stroke his chest.
“My turn”, he proclaimed, after I’d chucked his top in the wash on a quick cycle. Oh no, here comes the curry powder, I thought to myself, thinking about whether it was worth the risk of a forfeit, but that wasn’t quite the dare he had in mind.
“Take your top off” he demanded. I paused for a second. From one point of view it only seemed fair he got to see me topless seeing as I was the reason he was now walking around just in his shorts but I knew I just had a little lacy bra on underneath. Do I risk the “truth” question? Fuck it, it’s only Jack. I’ll be fine, it’s not like he hadn’t seen me in a bathing costume before, so I took the top off.
I noticed how intently he was watching as I slowly pulled the top up over my head. I could see that chest moving in and out as his breathing started to get a little deeper. This is different, I thought to myself. He’d never really shown any interest before but he couldn’t keep his eyes off my breasts. He was taking it all in and it felt kind of nice knowing I was having an affect on him.
It was my turn again. I noticed a bulge forming in those tight shorts of his. Now I was curious. I’d never seen a guys cock before and it just seemed too good an opportunity to turn down. “OK, I want you to pull down your shorts and boxers” I asked.
He was clearly embarrassed. He knew he’d have nowhere to hide that impressive swelling in his pants. I was expecting him to take the question instead so I started thinking about what I should ask, it would have been “have you ever thought about me whilst you touched yourself”, something I was very curious about. I didn’t get to ask the question though.
He gingerly slid his palms into the sides of his shorts, closed his eyes and began to tug them lose. They really didn’t want to come down though as his stiff cock held them tightly in place, but with a little more force, they were down.
My, oh my. It was a sight to be seen. It was standing firm to attention, as if it was staring straight back at me. I could see the veins sticking out and his balls hanging down. He kept his eyes firmly shut as if by not looking it meant I also couldn’t see. This was even better though, I could stare guilt free without him knowing how impressed I was to see him so painfully hard. But fuck, now it was his turn and I had made him strip for me. What would he make me do in return?
I couldn’t believe the words that came out of his mouth when he asked me to “suck it”. I had always been curious about what that would feel like but I never thought it would happen like this, with my best friend. I pretended I was offended by the request but secretly I couldn’t be any more excited about putting that thing in my mouth.
I knelt down underneath him, looking up. I knew he could see straight down my cleavage as I watched his face react to my mouth being so close to his cock, anticipating what I was going to do to him next.
I kissed his thighs gently and felt my heart pounding with excitement. I closed my eyes and stuck out my tongue slightly, making contact with the underside of his shaft. It felt so warm. I loved the sensation as I licked all the way from the base of his shaft at the top of his balls to the tip. He pushed forward a little and took a deep intake of breath. I opened my eyes and noticed a small drop of transparent, thick fluid at the tip of his shaft and I wondered what it would taste like.
I licked him clean. It didn’t really taste of anything but it was frilling to know his cock was responding to everything I was doing. I grabbed the base of his penis, pulling that big hard cock downwards a bit so I could kiss the side of his shaft with my lips. It was a nice combination of soft skin and hardness as the same time.
I wrapped my lips around his tip and slid him into my mouth. He let out a big groan. I wondered how that felt for him and what he was thinking about. Was he imagining what the insides of my pussy would feel like against his cock? If only he realised how soaking wet I was down there by now, he could have got away with anything.
I worked that shaft real good with my lips. I tried to stick as much of him as I could in my mouth, still holding onto the base with my fingers. I gave his balls a good stroke with my other hand. His body seemed to react, getting tenser, the more I sucked that cock up and down.
He put his hand on my shoulders, pretending to massage them but really he was just stopping me from withdrawing. I could tell he was enjoying the sight of seeing his shaft disappearing into my mouth. I looked up at him with puppy dog eyes whilst I carried on working my way up and down that shaft, applying more pressure with my lips and my tongue from underneath.
He began to thrust along with me, matching my rhythm. I felt his balls firming up as if something big was going to happen. He was moaning with delight with every thrust. I twisted my mouth as I got closer to the head of his cock. He tensed up. His grip on my shoulders became very firm and he wasn’t letting me go anywhere then I began to feel this pulsating sensation and jets of his warm spunk hitting right at the back of my throat.
I felt great satisfaction knowing I made him cum inside my mouth like that. It was an experience I’d never forget and I swallowed every last drop, I didn’t have much choice as he was still holding my shoulders so I couldn’t escape from his cock.
We had a lot of fun that summer as I perfected my technique. He loved to return the favour too, I was always very wet after doing that and he lapped it all up! I guess you could say we became friends with benefits, and what a nice big benefit he would deposit in my mouth.