Last Summer First Time

It was the last summer that our group of friends would be together and we filled it with daytime outings and parties each evening. We wanted to spend as much time as possible with the friends that we would no longer be as (physically) close to next year. High school was finished, we had graduated and were moving on to different colleges, different towns, separate lives. Our tight knit group of friends was splitting up, but we made promises to always keep in touch. September was just one week away now and everyone would be leaving in the next few days.

After one of our summer parties at your house I found myself upstairs on the bed beside you with our close friend Matt also there. We had been drinking steadily during the party and it was now very late, we were in that happy but tired late night state. I'm not even sure how the three of us came to be upstairs in that room together but it turned out to be one of the most memorable nights of my life.

We were all talking and laughing together, you were laying on your back sandwiched between Matt and I. We snuggled up closer to you and pressed our bodies into yours. It was all very playful but there was a powerful sexual tension building. Following Matt's lead I reached out and started making small circles with my fingers on your flat stomach, then moving up to touch your ear through your long hair. You had on a cotton top and very small very tight jean shorts. I ran my fingers up and down your bare leg, then up over the small strip of denim to your abdomen. I slid my hand up to your ribs and stopped just below your covered breasts. Our caressing went on for some time. Becoming a little more bold I moved down and tucked the tips of my fingers under the waistband of your shorts, feeling the top of your thin cotton panties and how they hugged your small hips.

All the while Matt had been doing the same on your other side, and then I noticed that he had grabbed the side of your underwear and had pulled it up out of your shorts and over your hip. He was tugging on it and making you laugh and squeal. I joined in and grabbed my side, pulling it up just as high. I hoped that we weren't hurting you, but your smiles and laughing reassured me that it was all OK with you. I wondered exactly where the fabric was rubbing and how your tender bits were responding. Whispering in your ear I asked if you were alright and you nodded yes with a big smile. Our pulling continued and I heard a ripping noise come from Matt's side, you cried out when you heard it, but he pulled even harder and I saw the fabric of your panties come away in his hand. I was surprised and had stopped pulling on my side but you were still smiling so I tugged on the fabric again and without much resistance shreds of your underwear were in my hand. We all thought this was hilariously funny and you jokingly chided us for literally ripping the panties off your body.

Matt and I remained on either side of you, lightly caressing your smooth skin with our fingertips. The situation was exciting but also tense and slightly uncomfortable, where to go from here? After a while you shifted your hips and turned to me, you whispered how much you liked me, and how you wished that things could be different. We were so close our faces were almost touching, our eyelashes brushing against each other, then our lips met. We kissed very lightly at first, but our mouths opened bit by bit and soon our tongues were playing together like old friends. Graciously Matt sat up and told us he would go so we could have some private time together. Before I could say anything he got up and walked to the door, leaving with a smile and a wave. I thought that was such a cool and considerate thing for him to do.

Alone now we kissed more passionately. We embraced each other tightly, then started to move our hands slowly over each other's body to explore every inch of skin. I rubbed your small ass through your cutoffs, those shorts were so tiny that your cheeks were exposed where they met your thighs. I brought my hand up to your chest and cupped your firm breast, the nipple was hard and pressed into my hand through your shirt. Your delicate hands were roaming all over me as well, stopping at my crotch you rubbed my hard cock with your palm through my jeans. We continued to kiss open mouthed while I slid my hand down over your ribs and stomach, past your waist, then further still. Your shorts were so tight that I could barely get my fingers inside them. So I opened the button and with difficulty pushed the zipper down. Sliding my hand down the smooth flesh below your belly button I felt your soft hairs there. I was surprised at first that you didn't have underwear on, but quickly remembered how we had savagely removed them from you. I thought that maybe maybe your skin was sore, so I decided to touch you extra gently.

I slid my fingers down a little further anxious to touch you for the first time. But even with the fly open your shorts were too tight for my hand to fit and only the very tip of my middle finger could reach down far enough to feel the top of your soft groove. I pulled my hand out and started to rub between your legs through the denim, it was warm there, and kept getting hotter the more I massaged you. You rocked your hips back and forth against my hand as we breathed deeply into each others open mouths. Reciprocating, you deftly undid my jeans and slid your hand into my underwear and wrapped your small fingers around the head of my stiff penis and squeezed. We both wanted more.

We pulled away to make enough space to remove our clothes, I grabbed each side of your shorts and slid them slowly down your smooth legs revealing a patch of fine pubic hair visible in the dim light. I helped you pull your top over your head to free your firm round breasts. For my part I stripped off my shirt and ripped off my jeans and boxers in a flash. Then I leaned down on top of you, to feel our naked skin press together for the first time was delicious. We kissed hard as my hand moved back to your breast, your nipple was bigger and harder than any I had ever seen. I thought it must be very sensitive so I gently rubbed and pinched it making you gasp slightly each time. Unable to resist I moved my head down and wrapped my lips around your engorged nub, flicking my tongue over it. My hand cupped your breast helping to lift it into my mouth. I licked and sucked while my free hand found your other breast. Then I lifted my face back up to meet yours in another wet kiss and simultaneously moved my hand down between your legs. My fingers found your small lips and I smiled when I felt how wet you were. I slowly ran my fingers up and down your sweet slit, from the bottom of your opening to the top above your swollen clit. The lips parted to allow my fingertips to slide inside a little so I could caress your most sensitive parts. Your hand found my dick again and you started tugging on it and squeezing hard. It felt so good and I started making small circles around your slippery clit to reciprocate.

Shifting your hips you pulled my cock to within a hair of your soaked pussy. I pushed forward and felt the tip of my head slide past your small lips. It was so warm and wet, and your juices made my head tingle. I pushed a little more, then even harder but I couldn't get even my head past your tight entrance. There was such a resistance there so I pulled away and slid the underside of my hard shaft up and down the length of your wet slit a few times. Your lips parted invitingly, lubricating the full length of me. Pushing down again I found your tight opening and applied pressure there. I still couldn't get my head past your tiny entrance though you were dripping wet. We kissed while I pushed down into you, and you ground up into me. I wanted to be inside you more than anything but I didn't want to push too hard in case I hurt you. It seemed like we weren't making any progress, then suddenly I felt an orgasm bubbling up within me. Gasping I pulled my cock away and shot stream after stream of hot cum onto your hips and belly.

Panting and a bit embarrassed you reassured me by reaching over to kiss me again. I slid my hand down to your hot box as we kissed and made circles around your super tight opening with my finger. Still circling I dipped my middle finger deeper into your wetness with each stroke, soon I was sliding my finger in and out with a long even motion. Your breathing was becoming hoarse. I was so turned on that I remained rock hard and wanted to try to enter you again. Playing it safe I fetched a condom from my jeans and carefully slid it on. Unfortunately the break in the mood while applying the condom and the clammy feel of it caused my erection to fade. I figured this was temporary and we kiss sloppily as I continued to slide my finger in and out of you. Our rhythm got progressively faster and you raised your hips up to meet my hand on each stroke. This went on for a while until I decided I should go to the bathroom and get rid of the useless condom.

I let you know and with a last kiss I rolled over and walked to the adjacent bathroom. I cleaned myself up in the half light of the early dawn. It seemed like an eternity that I was away from you though it was only a few minutes. Returning to the room I slid up beside you on the bed and when our bodies met it felt like we were back where we belonged. Kissing felt so natural and my cock sprang to attention again right away when my finger slipped back inside you and found that you were still as excited as before.

Now you took control, pushing me down onto my back you straddled me and I grabbed onto your hips, leaning down you rested your aching pussy onto my once again super hard penis. Taking it in your hand you guided it up into your opening. Pushing past your wet lips felt incredible, and you didn't ease up the pressure. Rocking in concert against each other my member slid millimeter by millimeter into you. It was working! The head was completely inside now, being crushed by your soft folds of flesh. The further I pushed up into you the tighter it was. Slowly and steadily we worked together on our goal of being united as one. After a blissful eternity I was finally buried all the way inside your small pussy, the feeling of being crushed on all sides was unlike anything I had ever felt.

Sliding confidently in and out we were breathing hard and you started to moan softly during each long exhale. Our pace increased, your tight lips gripping my shaft on every stroke not wanting to let it go. My orgasm built very slowly this time, like an exponential curve, each stroke bringing me steadily closer. There was no rush, I felt like I was in control right up to the end. You ground your pussy down into me on each push and I reached up deeper inside you than I thought possible. My cock felt huge, stretching you more than ever before. Pushing, pulling, faster, harder, I felt ready to burst, I grabbed your hips and pushed you away. Your hungry lips didn't want to let me escape, but I finally pulled out completely and shot another load of hot cum all over my chest and stomach.

Knowing that you still hadn't had a chance to orgasm I reached around your leg and quickly slid two fingers into your pulsing pussy. Your moans didn't skip a beat even though fingers were certainly no substitute for my thick cock. You pushed back hard into my hand and your moans got louder and louder. I could have stayed that way for hours, just contentedly watching your beautiful face as your orgasm slowly built, but you had already waited a long time for this. Breathlessly moving your ass faster and faster you were almost there. Suddenly you threw your head back and let our your loudest, longest moan yet while your body shook as you finally came. Your tight little pussy convulsed around my fingers as the waves of your orgasm shook through you. When your orgasm finally subsided you lay down on top of me in exhaustion.

We stayed that way together quietly savoring the moment. The morning sun was already peeking brightly out from behind the window blinds, other people in town would be waking up soon to start their daily routine, but for us it was time to rest. Slowly and contentedly we drifted off to sleep in each others arms, knowing that we were exactly where we should be.