I took my best friend‘s virginity after making him cum in his pants in front of all our friends.
I’ve had this guy friend ever since middle school: Tyler. He’s always been one of my closest friends; he’s who I’d go to complain and cry to a lot of the time. Everybody always said he was completely in love with me, and at first, I thought they just didn’t get us. But it became pretty clear they were right. He was kind of all over me. And it’s not even that I didn’t think of him that way; he just never stepped up and made the move.
We went off to separate colleges, as did the rest of our high school friend group, but we’d still hang out all summer every summer. After my sophomore year at college, we were hanging out a lot at my place since my family had gone on a summer vacation, and I was home alone. This all happened when Tyler and five other friends of ours (four girls and one guy) were all swimming at my place.
I wore this cute little plain, black thong swimsuit, really slutty. I bought it specifically because I knew my parents wouldn’t be around. From the start of our swimming, I kept catching Tyler looking at my ass. He didn’t notice that I noticed, but he wasn’t exactly being subtle.
Quick aside, so you have an idea of how I look: I’m about 5’5″, brunette, with shoulder-length hair at the time, a small waist, a little on the skinny side, C cups, but some hips and a pretty big ass. Tyler was kind of skinny, baby-faced, but still good-looking. He just had no confidence.
Anyway, I must have seen Tyler staring at my ass at least a dozen times while we were swimming. One of our friends, Casey, suggested, “We should have a chicken fight!” So I, wanting to have some fun, immediately shouted, “I call Tyler!” He went underwater and picked me up on his shoulders. I made sure to immediately move forward so he could feel my pussy pressing up against the back of his neck.
We had one round, and Casey beat me pretty easily, so I got back on and said, “Hold me further up on my thighs, it’ll be sturdier.” It wasn’t sturdier at all, which I knew it wouldn’t be, but I was having a lot of fun messing with Tyler.
We had all been drinking, and by evening, we started feeling a little drunk. Eventually, we were all out of the pool and drying off. I was rapping along to some song playing on the speaker and jokingly twerked up on Sydney, another girl there. She grabbed my hips and grinded up on me, holding her beer up in the air with her other hand and wooing. So I bent over and tried throwing my ass back as well as I possibly could.
Tyler and Danny, the other guy there, were both sitting and staring at me. They had been smoking a little bit of weed, but stopped smoking and were just staring, mouths open. I locked eyes with Tyler and kept going for it. After a while, I turned around and danced facing Sydney, shaking my ass a bit more, really putting on a show.
I don’t know why I was teasing Tyler so much all of a sudden. I’ve always loved doing things like pulling my shirt down a little bit when he’s not looking and calling him out for staring at my cleavage. Other stuff like that, but it’s just been little things. I’ve never really gone at it like this before. Maybe I had been too slutty at college and it was getting to me. Or he was finally starting to look a bit older and sexier. Maybe I was just feeling a little mean.
Anyway, cut to later that night. It was about eleven and we were all hanging out in my living room. We had ordered some pizza, ate, and were still drinking a fair amount. We played some games (we always end up playing games like Truth or Dare, Never Have I Ever, Paranoia, The Yellow Light Game, etc.). After some tamer rounds of things, we broke out a Jenga set I had made freshman year of college. It was a normal set that had either truths, dares, challenges, or requirements to drink written on each piece you pull out.
This was, surprisingly, the first time I had broken this game out with this group. I usually would bring it out with my sluttier, drunker college friends. We were drunk enough that we were all in the mood, though. A couple of fun things happened. Tyler had to give Danny a little peck on the lips. I had to kiss Casey, but we let it turn into a full-on makeout for a second there. Kylie, another girl there, had to turn all the lights off, flash us, and then turn the lights back on. Danny made out with Alison, the last girl there. Stuff like that. Mixed in with truths about our slutty encounters at college and a fair amount of drinks.
Anyway, things started taking a turn when I got a piece that said to take off an article of clothing. I was just in a bikini, so I asked, “how long does it have to be off for?” We all decided on thirty seconds. So I took my bikini top off, and people looked and giggled and it was pretty chill. Except Tyler was straight up looking in the other direction.
I teased him. “What’s wrong Tyler?” He said he wasn’t sure what to do with his eyes. “Would it make it better if I told you to just stare for a bit, get a really good look?” I asked, giggling. So he turned his head back around and looked, almost locking his eyes on them. He blushed badly and got flustered. Something about fucking with him was starting to turn me on. Kylie yelled, “Thirty!” and I put my top back on. We kept playing for a while and things got back to normal pretty quickly, for the most part. Tyler was still a bit shaken up I could tell, but I kept shooting him looks.
I had some truths and drinks and the next time I got a dare, it was to give one person playing a lap dance. So I immediately mounted Tyler. I turned up the Spotify playlist we had on in the background, and started grinding on him. Our thirty-second rule was still probably in play, but I didn’t time anything out. I just kept going for the whole song.
Moving my hips in circles for a while, I put my face up in his, letting my lips get close to his, flipping my hair, and making eye contact the whole time. I let my tits brush up against his bare chest a little bit. After a while, I turned around and just bounced my ass right up against him, facing away, letting him stare at it. The other girls were cheering me on; they were super drunk. More so than me and Tyler, who were tipsier.
I turned back around after another thirty seconds or so and sat on him again. This time he was visibly nervous, and I realized it was because he was rock-hard in nothing but a swimsuit. I should have stopped, but I grinded up against his cock. I let myself get carried away and tried to stroke him with my ass, clenching and trying to squeeze on his cock a little. He breathed heavier, and I moved his hands onto my hips. The song was almost over, so I leaned up to his ear and whispered, “I didn’t know you were so big Tyler” and giggled.
He moaned under his breath and suddenly went completely red. Pushing me off, he stood up, and walked across the room to grab his clothes and his stuff, clearly really upset. He was still hard and had a big wet spot on his swimsuit now. It became clear that I had made him cum. “Oh my god!” I laughed. I was smiling pretty big but tried to hide it. The other girls stifled some giggles. I tried to say sorry, still smiling a bit, before he interrupted me, almost shouting, “No, you knew what you were doing! You’ve been fucking with me and laughing at me all night!” He grabbed his stuff and started trying to leave.
I stood up, trying not to smile, and said, “Tyler, relax, I’m sorry. Why don’t we go back to my room and talk.” He agreed, and we left the rest of them out there to watch youtube videos and went to my room and closed the door. Once we closed my door, he sat on the bed. He looked like he was about to cry. “I don’t get why you decided to pick on me today,” he blurted out. “I wasn’t picking on you,” I said. “But you know I like you! I know you know I like you! You’re just torturing me and rubbing it in.” I didn’t know what to say. Finally, he just asked, “Why?”
“Because you’re hot Tyler. And I like watching you get all embarrassed. I like the way you look at me. And I think I wanna fuck you.” He seemed dumbfounded. He didn’t say anything for a while. “You wanna fuck me, right?” I asked, “’cause I’m saying I wanna fuck you.” He just stared at me, as if he wasn’t sure if this was real. I loved how confused he looked.
“I’ve never done that before,” he said quietly after a while. I was surprised. I knew he was sort of innocent, but he was good-looking and in college. “Wait, are you a virgin?” I asked. “I had never even seen a girl topless until tonight,” he confessed, blushing again. I smiled. “Do you wanna kiss me for a bit?” “Okay,” he said, “but I don’t wanna be a sympathy case.” “I promise you, I wouldn’t do that,”
Leaning in close to him, I closed my eyes, and grabbed his neck just behind his ear. I let him move in most of the way, and I gave him a long, passionate kiss. I kissed him again and again. Soon, I let my tongue lightly brush up against his bottom lip. He got the hint and started making out with me. He was following my lead, but he was a really good kisser. I could tell how passionate he was about me, and I felt my nipples get hard at the thought of how much he wanted me.
I moved his hands to my hips and kept making out. “Oh my god,” he sighed. Working up the courage to move a hand onto my ass, he felt around. He held my cheeks, but I had to move a hand down there and squeeze his hand to get him to squeeze my ass. Grabbing a handful of my ass in each hand, he began feeling me. “Harder,” I whispered between kisses. I threw my head back, and he kissed and licked at my neck. He gave me a hickey, which I loved.
I let myself fall back onto the bed. He crawled over me and kept going at my neck. He worked his way down to my collarbone, so I untied the top string on my bikini. I could tell now that he was starting to get hard again. He kept working his way down my chest into my cleavage, so I pulled my bikini top off completely. “Oh you’re so fucking hot, oh my god,” he whispered, and sat up, grabbing my tits. They fit so perfectly in his hands as he gently squeezed and bounced them.
“God, use your mouth, Tyler,” I said, back to the teasing tone I’d been using with him all night. He kissed his way to my nipple and began flicking his tongue on it, sucking, nibbling at it. He kept muttering, “Oh my god,” under his breath and squeezed my other breast with his free hand. Looking up at me, he said, “Your tits are so perfect. You’re the sexiest girl I’ve ever seen.” It felt nice being with someone who meant it when he said things like that.
I wrapped my legs around him and made out with him hard, biting at his lips a little and digging my nails into his back. He began grinding up against me, and I could feel how big his cock was right up against me. “You wanna lick my pussy, Tyler?” I whispered in his ear. He barely whimpered out a little “Yeah,” and I spread my legs and looked him dead in the eyes. Crawling back a bit, he shoved his face between my thighs. He started kissing around my inner thighs and licking right at the line on my little thong bikini. I could feel myself getting so wet.
“Take it off,” I told him, “You think you can do that for me?” He peeled my bikini off of me and stared at my pussy for a little while, completely clean-shaven since I’d been in a bikini a lot lately. He crawled towards it, and I was so wet it looked like I had been oiled up or something. Saying, “You smell so good,” he made some big, slow licks up my whole pussy. He kept doing this, hands digging into my ass, pulling me into him, letting his tongue slide right between my lips. I was trying not to squirm as he worked his tongue in little circles around my clit.
He got more adventurous; I think he was doing the alphabet trick or something, but it was working. I was really surprised since he said he had no experience, but he was so attentive. He cared about my pleasure a lot. “You’re so perfect,” he said. I moaned and blurted out, “I want you to lick my asshole.” He panted some and dove down, moving his tongue in little circles around my rim.
I moved my hips a little, really riding his tongue. I was getting wetter and wetter, I’m not sure if I had ever been this wet. “Oh my god, you’ve got me so hard,” he said. “Show me,” I shot back. He stood up and pulled off his swimsuit. His cock was probably about seven and a half or eight inches, and about average girth for that size. It was sticking up and had a teeny bit of precum dripping out of the tip. My jaw dropped. “Oh my god, Tyler!” I laughed. He smiled, seeming slightly more confident, finally.
I got off the bed and got down on my knees and spit in my hand. I stroked him, making sure I got everything nice and wet. After a while, I pulled my hair back like I was going to make a ponytail and handed it to him. He grabbed my hair, and I wrapped my lips around his cock. “Oh fuck,” he moaned. I made sure to lock eyes with him as I started sucking on him, bobbing my head up and down. Finally, I went all the way down to the base, letting him slide down my throat, and I kept looking him dead in the eyes. “You’re so fucking hot,” he whispered again. I held it there until my eyes were watering, and then pulled back, letting my spit pour out of my mouth and onto my tits.
Stroking him with my hand again, I took his balls in my mouth, one at a time. I licked my way back up his shaft and put my lips on his cock again. Sucking on him, I ran my tongue on the underside of his head for a while, and then pulled back. I stood up, walked right up to him, wrapped my arms around him, and let my still-wet pussy brush right up against his cock.
“You never answered me earlier. Do you wanna fuck me, Tyler?” I batted my eyelashes at him. He grabbed me and shoved his tongue into my mouth, digging into my sides with his hands, and walking towards the bed. He pushed me down onto the bed and got on top of me. I spread my legs for him, and he grinded his cock on the outside of my pussy, letting the shaft ride between my lips. He panted and grunted, tossing his head back. He leaned down and said, “I don’t have a condom.” “I don’t care,” I said. Tested fairly recently, I was also on the pill. I knew he was a virgin, so I wasn’t worried about him.
He gave me a long, passionate kiss, took the base of his cock in his hand, and moved to go inside me. Not having the best aim. But I’m pretty good at shifting around and helping guys get in. He slipped inside me fairly quickly; he felt even bigger than he looked. He closed his eyes and thrust back and forth slowly, savouring it. “Tell me about it,” I giggled, “Tell me how I feel.” “You’re so warm. And it’s so smooth,” he said, “you feel so good.” I leaned in for a passionate kiss, but instead bit into his lip, hard. He grabbed my shoulders, pumping into me harder and faster.
“How about you flip me over,” I moaned. He pulled out and grabbed my arm, still kind of gently, and I got face down ass up for him. He slid back into me, and I moved this time, bouncing my ass onto him while I shoved my face into the mattress. I let out a little whimper every time he thrust into me and hit me just right in that spot. “You have the most perfect ass I’ve ever seen,” he said. I loved how much he seemed to worship me. “I know,” I responded.
He stopped to catch his breath for a second, so I told him to get on his back. He laid down, and I got up on top of him and started riding him. I moved my hips in little circles while I moved up and down on his cock. He had his eyes closed and grabbed at the sheets. “You’re so fucking big,” I told him, “I love feeling your cock inside me.” He looked like he was getting close, so I got off, leaving him on the edge.
I laid back down on my back, and I told him to fuck me as hard as he could. Holding my thighs, I put my feet up over his shoulders, letting him bend me in half. “I want you to hit it as deep as you can,” I said. He began thrusting in, slamming away at me. I whispered, “How does my cunt feel, baby?”
“I’m about to cum,” he groaned. This put me right on the edge too. “Cum inside me,” I said, “I want you to fill me up. Do you wanna fill me up, baby? Do you wanna fill my pussy up with your cum?” He started cumming, holding himself deep inside me. I licked my finger and rubbed it back and forth on my clit. “Can you keep going for me?” I said. He did, and soon I felt my leg shaking. “Oh, I’m cumming for you!” I screamed. “Cum on me,” he said. I came for probably about a minute while he moved back and forth gently. He pulled out and took a big breath.
“That was so amazing,” he said, “oh my god, oh my god.” I cuddled up against him for a while, kissed his cheek, and ran to the bathroom to clean up. We talked about how crazy it was we had never done this earlier. We both got dressed and headed back out to everybody. They didn’t say anything, but I’m sure towards the end they could hear me moaning and shouting. We all finished the movie they had put on and people fell asleep on the couches and floor. I took Tyler back to my bed and we fell asleep.
We were some kind of a romantic thing for the rest of that summer, we never really labelled it, and it was pretty nice. Once it was time to go back to college, we settled on a sort of friends-with-benefits situation. That lasted until he got a girlfriend a year or two later, and we went back to just being close friends. But while it lasted, it was some of the best sex I ever had.