Where it happened: Hawaii
Langauge: English
Sex: Female
Rating: 5
Category: Straight
I lost my virginity recently when I was in Hawaii for a cheerleading competition for my high school. At the time I was 14, and would be turning 15 in a couple of days. We stayed at a Hilton hotel in Honolulu for five days. One of those days, we all had the chance to go anywhere in the city we wanted. Most of the girls went shopping for clothes, but since it was so hot outside, I decided to go to the hotel swimming pool. So as I walked pass the pool, I saw this totally hot lifeguard. He was pretty old, I thought maybe 18 at the time (later I found out that he was actually 29 years old).
I don’t know why, but I wanted him…so bad. So when I walked back to my room, I looked for something cute to wear. I brought a bunch of swimwear, so I chose this totally cute bikini. It was really small and tight and you could see some of my butt crack J. I also tried to make my boobs stick out (fortunately, I had “matured†a lot). I put on some red lipstick before going down. I’m usual don’t dress to get men like that, but this was the first time in my life that I felt this way. I had boyfriends before, but I always fantasized about an adult.
When I got to the pool, I saw that he was packing up his stuff and another lifeguard was starting his shift! I didn’t know what to do. I can’t remember why I did this, but I just kinda went with my instincts. So, I sat down on the beach chair next to his chair and asked him to put some sunscreen on me (I know it’s the oldest trick, but it can work!). He said “yeah, sureâ€Â. I handed him the sunscreen and he rubbed my back. He worked his hands down to my hips, I think that he was feeling me up. I turned around and smiled at him. He told me that he would be staying at the pool for a little while and asked me to apply some sunscreen on him. His body was soooooo smooth! Boy, am I lucky that he was totally buff. I knew that he MUST have a girlfriend or even a wife. He was wearing a tight little speedo, and when I was rubbing his back, I decided to take it up a notch, I reached around and squeezed his penis from the outside of his speedo. I put my hand under it and ran my fingers through the thin patch of his pubic hair. He moaned, so I stopped, and I didn’t want to attract attention towards us. He suddenly blurted out, “do you want to come back to my apartment?†I was really surprised that he would be interested in a little girl like me. When we walked out to his car, he held my hand, I felt like I WAS GOING TO DIE!
When we got into the car, I leaned over to kiss him. It was kinda weird cuz of his stubble. It was like the really short hair that’s sharp, and his whole face was bigger than mine. I’m 5’4 and he’s like 6’3, and he’s built much bigger than me. So anyways, on the way up to his floor, he had his hand on my butt the whole time and I had gotten him back by rubbing his crotch. He opened the door and playfully threw my on his bed. By now, he had a huge erection. I was really scared, because I wasn’t looking to make love with him. But he got on top of me, and he took off his shorts. His penis was really hard and was throbbing and twitching. It must have been like 10 inches long, so by now I was breathing really hard and was scared to death. I thought that I wouldn’t have to have sex if I made him come. So I reached out and touched the tip of it. He kinda pulled back, like it hurt. So I just looked into his eyes and kissed the tip of his cock, near the hole. He was breathing really hard now and I basically was making out with his penis. I think that he was uncut, and I heard that you’re more sensitive if you are. Anyways, I tried to go down on it, cuz it was really to big, and I gag really easy. He was moaning with pleasure, almost like I was hurting him. So I just went up and down until he yelled and he came in my mouth. It was sooo warm and it tasted really salty. I was kind of mad that he would just do that, so I just smiled at him, and then kissed him on the lips. In doing so, I spat it all in his mouth.
We both laughed, and he lied back on his bed and pulled me on top of him. His cock was across my tummy. There was still sticky liquid all of his penis, and now on me. I was still dressed, but for some reason he started to hump me anyways. I really didn’t want to have sex, so I told him that I was gonna go take a shower. I walked to his bathroom and turned the shower on. The water was nice after having his sperm all over my belly. I heard the door open and saw him come in. He opened the shower curtain and looked at me. I blushed, I don’t know why. He picked me and put me back down on his bed. I was completely wet from the shower still. I told him that I wouldn’t have sex with him, but he said “just let me enter through your buttâ€Â. I know that he must have been really horny (imagine that, a 36 year old with a little 14 year old girl in his apartment!). I agreed, and he started kissing me all over. He reached over to his nightstand and pulled out of bottle of “KY Jelly†I think it was called. He asked me to relax my butt and just take deep breathes. The lotion he had was warm feeling and he put some on his fingers and started gently feeling my hole. It was weird, but it was really hot when he slowly pushed his finger up into me. He got more of it and really made sure that I was well lubricated. Finally, he asked me to rub his dick down with the jelly. I took his pulsing penis into my hand and I put plenty of jelly all over it, I didn’t want it to hurt that bad.
He took his dick and pushed it gently against my hole. Nothing happened, so he took his hands and grabbed my hips and started to push REALLY hard. His dick slid right in, I felt the whole thing go into me. And believe me, it hurts SO BAD to have the whole thing up my rectum. I liked it though, I felt SO close with him at that point. He started to pump really hard, I remember I was screaming with pain and he didn’t even care. It was sliding in and out pretty easy by now, no condom J. He was lightly touching my vagina, and it felt SO good. When he tried to actually enter me with his finger, I yelled “Hey!†and slapped his hand. I thought that it wasn’t enough for him, so I started to push back and slide up and down on him. He was moaning and I saw his eyes rolling back! I grabbed his balls and I touched his asshole. He started shaking and he yelled and came AGAIN up my butt. He moved backwards and forwards a couple of times and basically collapsed on me! He wasn’t too heavy, but having a 36 year old MAN all over me was kinda scary L. He was fighting to catch his breath and was still shaking. He got off of me we both layed on our sides, his huge dick still all the way in me. He just kept saying “I love you†and he would kiss my neck and rub my butt. The pain in my butt was going away, so we decided to take a nap, I had to check in at 7:30 and it wasn’t even 2 o clock yet. I remember that he just held me in his arms on the bed. I felt safe with him, and even though I was somewhat scared because I knew that he wanted me, I knew that he would keep me safe. I loved the way his muscular, hairy chest felt on my smooth back. When I woke up at 5 o clock, he was still asleep. His dick was STILL in my ass, which was REALLY sore by now. IT HURT SO BAD! With him still sleeping, I pushed down with my butt to slide his dick out. The whole time it was burning, and the head of his dick wouldn’t come out. So I took his half erect penis and pulled it out. In doing so, A LOT of semen leaked out of my butt and he had another ejeculation. He moaned and opened his eyes. I was hoping that I could leave before he woke up. He put his hand on my thigh and started rubbing me. I tried to resist by saying “no†in a whiny voice, but he just couldn’t take it. He pulled me on top of him, so that I was lying directly on him. This is when I realized how much bigger and he was, and how he was an adult and I was just a kid. He was a grown man, not some boyfriend, and I was out of my league.
He gently kissed my breast and slowly sucked on the end, and I felt his penis harden and was sliding across the opening of my vagina. I started to cry, just because I was so scared L. I knew that all he wanted to do was make love, but I didn’t think I was ready. He put his arms around me and I rested my head on his chest. He whispered in my ear, “it’s gonna be okâ€Â. It was really weird when he took his cock and started pressing it up against my butt again. I told him how much I hurt down there, and he asked if he could “put it in my vaginaâ€Â. I knew then that he wouldn’t let me leave until he took my innocence. He reached into his nightstand and took out a condom. The XXL label on it reminded me of how hard it was going to be to fit him all inside of me. He asked me to put it on him. So I undid the wrapper and place it the rolled up condom on his penis head. The tip was covered in a sticky liquid, and the shaft’s veins were throbbing like crazy. When I touched it, the whole thing did this twitching thing. He asked me to lie on my tummy, so he could enter my vagina from behind. So, I got off of him and lied next to him on the bed. He got on his knees and kissed my butt cheek, god he was obsessed with my booty! He didn’t bother lubricating me, the condom already was. He touched the head to the opening of my vagina. He told me to just relax and go along with it, although my eyes were already welling up with tears. He tried pushing in to me, and I felt a lot of pressure down there. He kept trying, but it wouldn’t go in. He was only lightly pressing though. Somehow, I started to get turned on, just seeing him there treating me like a woman, not a kid. I told him, “Push! Just push!â€Â. With that he grabbed my hips and gave me a hard thrust. It just slide right in, about half of it! I almost lost my breathe, and I remember screaming a lot. It was a mix of pleasure and extreme pain. I just put my face in the pillow and just let him go at it. It was amazing though, just feeling him go in and out, all 10 inches of him. When he was completely in, he picked me up by the thighs and just had me sit on his lap. I rocked back and forth, and he was dying. I could tell that he was holding back from an orgasm, so I started going harder and faster. Before he came, he grabbed my sides and I felt his dick jerk upward. We were both breathing really hard and sweating a lot!