The First & Second Time

Autumn, 2010

I woke up one Monday morning at a decent hour after a late night as my college schedule showed that my only class was at 3:00 PM. Plenty of time to get up, get food, do my usual thing and relax before attending that one worthless hour. I looked at my phone when I saw a text from her. She had in fact timed it right and sent it at the correct hour, asking me to instead give up my free morning and early afternoon to come in to college and see her. I decided since she just got out of class, I invited her to come back to my house until I had to leave.

She was one of my best friends at the time and had been for the first couple of years into college that were both tough for us. We met on our first day in college, 2008. I had developed strong mutual feelings for her over the years however I never understood this particular side of her, she seemed to be rejecting a relationship for reasons unknown regardless of how many times I asked her about it. Yet she was so quick to openly flirt with me in texts and personal conversation. I invited her back to my house while going to the college to pick her up, we spoke on the way back. I wanted to find out once and for all why she wouldn’t consider a relationship but was still leading me on all this time. I got more than I bargained for, despite being heavily attracted to her. She had quite a plumper/busty build and was multi-nationality but I still loved her body. Something about busty/plumpers makes me want to jump on them quicker than a skinny/average girl would.

When we got back to the house, I had been pondering on giving her a more-than special birthday card as it was not a card for a friend but a girlfriend. I was a bit shy when I handed it to her in my bedroom, she sat on my bed and I closed the curtains as well as closing the door and turning on the lamp. She read the card and I saw the bright smile as it had impressed her. I felt like I had made the right move and couldn’t wait any longer, I lunged forward and leaned down to kiss her in surprise. She seemed to accept it without struggle however did ask “What are you doing?” in a silent whisper during the kiss. I did not respond and kept kissing her until we were laying on my small single bed together. She told me that she can’t accept me as a boyfriend because she is afraid to hurt me like she did to ones before me, however treated me like a fuckbuddy and openly admitted it. It felt wrong and I was raised better by my parents but the moment had caught me and I was now a fool in her play. I enjoyed it.

Minutes more into the kissing, I had removed the jacket that she always kept over herself, for the first time in memory I had seen her clothing beneath it (She literally never took it off, she loved her jacket). I then caught a glimpse of just how big her breasts were, asking her, “How big are they?” with a response, “E’s”. My mind lit up, I wanted to get in those quick having a fetish for breasts. I unbuttoned her thin dark gray top and let her remove her bra. I got a good grasp of the 100% natural pair, they felt amazing and her nipples dark brown to blend with her dark skin (she was part indian). I pulled her jeans off her also removing my clothes myself, having just my underwear on while she also had hers on to. I threw our clothes to the floor, at this time in the morning my parents were asleep and sisters at school hoping we would not be disturbed. I laid down in my bed and got under the sheets when she climbed on top of me. I felt her white patterned panties (they were normal knickers) on my dick which was already erect from her breasts earlier. I felt how tight the panties gripped her waist and also caught a rub of her pussy lips through the fabric of her underwear.

After she grinded on me for a while (dry humping) she wasted no time and wanted no fuss in positions, I asked her to give me a blowjob but obviously not liking them (I have never received one), she climbed under me and pulled her panties off after I removed my pants too. She whispered “Fuck me.” as I climbed on top of her in the missionary between her legs and wasted no time myself. She grabbed my cock and guided me into her pussy. I pressed inside, feeling a slight warmth but it rubbed my cock’s head and shaft so good. I closed my eyes and gave a slight gasp of breath feeling it. I looked down at her body, the dirtiest thoughts going through my mind as I pulled out and pushed in again. She was moaning beneath me, I began getting faster pumping in and out of her plumping pussy, she tightened her inner walls around me to make it feel hotter. Fucking her was like a cushion and I loved it. She looked at me half way in, I took a moment to catch my breath and grabbed her big thighs, loving her plumper/busty build and pulled them together in front of me. This made her feel much tighter and better, I pushed right into her on the bed and humped her pussy relentlessly.

We were interrupted as I heard movement upstairs, we got our clothes on as my mother came in to my room almost catching us. Introducing her and shooing my mother away as quick as I could, desperate to get balls-deep in her snapping pussy again. My mother soon left my room and left us to our time. I knew the risks were higher but we were both too horny to stop now. She laid back on the bed and left her top on but her jeans were off under the sheets for cover. I kept my top on as well with my trousers down. Before I knew it, I was missionary and cock-deep back into her thick tight plumper pussy pounding away.

Being my first time, I was always curious to experiment like I saw in porno’s. I asked her to change positions but she kept saying no and to keep fucking her with my 8 inch cock that she seemed to only want me for. After she guided me back inside her I kept humping away in missionary on top her. Soon losing the sheets careless of privacy risks and were only wearing t-shirts while fucking eachother. It soon started to feel like I could not stop, I was scared inside as I had just remembered we did not get any condoms. She said she preferred it without but would not allow me to cum inside of her regardless of how much she wished I could. In time, I moaned down at her “I’m gonna cum!”, in her response she immediately said “Pull out.”. Leaving it almost a second too late, I whipped out just in time and squirted the biggest load I had ever seen from my cock all over her exposed stomach and pussy.

I quickly got us some things to clean up with. She wanted round two however I felt a bit scared to engage in it again without a condom, reluctantly rejecting her. She did not seem too impressed and wanted to leave early.

The Second Time, Spring 2011

After our first time, we grew closer and I felt more and more perverted the longer I was around my now named ‘Fuck buddy’. My mind kept on her constantly as well as memory of my first time. I wanted to have sex with her again, soon. That time came quicker than expected again, I found myself in my bed with her on one evening in Spring. This time, my parents were out of the house as well as my siblings which gave us freedom entirely. I told her I wanted more experimentation this time, she agreed to try a blowjob and other positions with me.

We quickly undressed fully naked and got into deep kissing, this time she wore full cover black panties that looked so sexy on her plump build. She was stroking my cock while laying on top of me under my sheets. She kept talking about how big my cock was in previous texts, it seemed to be the one thing that turned her on for this. I did not disappoint her. She ducked her head under the sheets reluctantly and began briefly sucking on my cock. It felt suddenly more sensitive than her pussy but still good. After 30 seconds she did not like it and stopped, however we quickly got in to her massive E-cups rubbing around my saliva-covered cock. Her tits felt as good as her pussy. She squeezed them together as big as monsters, rubbing my entire cock up and down between them and soft as satin.

I quickly got on top her again in missionary to warm up, guiding myself in and began quickly humping her pussy again like the first time. My mind instantly reminded of that warm tight feeling, she was amazing. My birthday was soon, she looked up at me while I kept humping in and out of her. She said, “I got you a present, early. I took the pill.”. Her face lit up bright, I knew what that meant, being able to cum inside her for the first time. I kept pumping in and out her tight plumping pussy. After ten minutes I stopped to catch my breath, wanting to try doggy style she bent over infront of me and allowed me to slide back inside her pussy. I wasted no time, humping back and forth and slapping her round slightly large ass, loving it. She constantly kept telling me to fuck her, however she favoured the missionary with me over anything and soon got me back on top of her.

We continued in missionary for another ten minutes after five of doggystyle. I felt myself ready to cum again, she grasped my ass and tightened her pussy around me, i felt her insides clamping my cock hard and her pussy milking me of cum. I squirted a big huge load inside her, pulling out with a slight gush for her pussy lips as well. I felt amazing but incredibly drained of energy. My parents came home after we cleaned up but we soon found ourselves getting into round two which I did not deny her this time.