After Mike popped my cherry, he continued to break me in. After the 7th or 8th time, he still hadn’t got his 9 inches all the way inside me. He got a little past halfway inside me on maybe the 5th through 8th time and I actually was still bleeding a bit each time.
It was mainly the same routine; I would go to his house after school, he would lead me to his room, undress me, suck my perky 34DD breasts, take down my tiny panties, lay me on his bed, spread my legs, position his thick long manhood to my tight vagina and gently push inside me. He watched my face and kept pushing until I would squeeze his arm. Then, eventually, he just couldn’t get all of himself all the way in me. Additionally, making the challenge more impossible, was the look on my young face and the arousing nature in which my breasts bounced with each push – he just couldn’t hold his cum.
Prom night. He planned to pick me up after I was at the prom for a few hours. I told my friends I was tired and that I would see them Monday at school. I went out front to where he told me to wait. He was already waiting for me and I made my way to his car. I was wearing a strapless satin prom dress. Truthfully, my boobs looked huge in that dress and my waist was tiny. I dug up an old polaroid from that night (https://imgur.com/iD7AcEe).
I got in the car and Mike said, “Ohhh fuck baby, I need to get you in my bed.” He kept reaching over and grabbing my boobs on the way to his house. We went inside and said, “Do you want some wine on your prom night?” I said, “sure.” After two glasses of red wine I felt just the right amount of buzzed. I was always kinda shy at that age. I loved sex with him, but I wasn’t too sure of myself.
He walked over to me and started kissing me really hard and passionate like. Grabbing my ass firmly, then kissing my neck and cleavage. “Ohhhh fuck baby, you have the nicest biggest boobs.” I loved that my body could have this effect on an older man. He was kissing my neck and said, “Tonight baby, I’m gonna get all the way inside you.” I really wanted him to. I knew it would make him happy and I kinda felt it would be more comfortable for me once he did. He said, “The problem Jennifer is you are so tight that I cum so quick, maybe if we can make me cum before I fuck you, then I can rest and we can do it again.”
I wasn’t too sure what he meant actually. I was thinking to myself, ‘It squirts more than once?’ He pulled down my dress, exposing my breast. He firmly grabbed my tits and started sucking away, giving each one equal time (maybe a bit more to my right titty – poor left titty). My pussy was soaked, I could feel how wet I was without even being touched down there yet. He said, “get on your knees Jennifer.” I went down to my knees with my dress around my waist. I had sucked his cock maybe once or twice before, but I wasn’t that good and it only lasted for about 2 minutes before he started fucking me. This time though, he told me to take my time, to really have fun. I reached up and started undoing his pants, zipped his zipper down, bit my bottom lip and pulled down his undies. BOING. His beautiful manhood was right at my face; dry, smooth, 9 inches, and just so hot.
I pulled down his pants all the way. I reached up and grabbed his cock, opened my mouth, and sucked on it. I didn’t just suck on his tip, I put as much in my mouth as I could and gently went down. Then back up. Then back down. He moaned and said, “Holy fuck baby, look at you.” I wrapped my arms around his waist and made love to his cock with my mouth. The other two times I sucked him i was nervous about the upcoming sex, but not this time. The wine and the fact that I was so turned on made me an expert little dick sucker on this occasion. “See baby, if you just do this for a bit, I’ll cum and then we can have sex and I can finally get all the way inside”, he said. It truly is a man’s world, isn’t it, because that seemed totally logical to me back then.
I was just sucking him up and down, nothing fancy like hair flipping cock sucking gymnastics, just a girl concentrating on her technique – up and down with her lips always on his shaft. Then, he started shifting a bit. His legs were started to move a bit. I think he really had to concentrate on cumming because he may have felt just a bit guilty that he was gonna unload in my mouth, considering I’d had no work-up to swallowing. “Ohhh fuck,” he moaned. He grabbed my head with both hands very gently – “Good baby, look at me . . .good jennifer, keep looking.” He started moving his hips, he reached down with one hand and grabbed my titty, squeezed, and then said, “Ohhh my fucking (deity) Jennifer, fuck yes . . .” Then right as I was about to ask if i was doing it right my lips briefly came off his cock and a rope of cum shot out and hit me right in the face, I was surprised and thought I messed up and quickly closed my lips around his tip. He shoved my face down about half ways and slowly pumped his hips every so slightly as his cock pumped and pumped about 6 more ropes of his cum into my mouth. His cum was swirling around my mouth and i tried to swallow, and . . . I DID IT. It was actually easier than I thought. I could feel his cock pulsing from the experience and he was sweating. “Ohhhh fuck jennifer, holy fuck,” he said. I gently let his cock out of my mouth and looked up, “Was that okay?” He said, “Ohhh yes jennifer, very good, are you okay, did you swallow it all?” I opened my mouth to show him it was all gone. “GOOD GIRL JENNIFER.” He started laughing, “I came right on your face once baby.” I said, “I know, its sticky.” I got a towel and cleaned my face.
I was walking around his room in just my panties. “Hey doll, put your dress back on and show me how you danced at the prom,” he said. So I did what he asked. He was on his bed stroking his half hard cock watching my gyrate my body. He loved watching me dance. Then he commanded, “Now take that dress off.” I stripped out of the dress only wearing tiny satin panties and my high heels. He told me to get in a doggie style position. “Jennifer I’m gonna fuck you like that all the time after I break you in.”
He put me on his bed on my back, spread my legs and pulled my panties to the side. His tongue went right on my pussy, it was swollen, wet, extremely tight, and eager for him. He was licking me up and down and I was moaning and grabbing his hair. He licked me for about 5 minutes and I started pulling at him to come up and get inside me. He grabbed the underside of my knees and put my knees to my chest. My swollen lips were fully exposed. I wanted him so bad. He spread my legs and put his cock tip to my lips and gently guided his tip up and down my slit. Then he slowly started to push in. There wasn’t any pain yet, it felt so fucking good. He kept pushing till his cock hit the wall again – half way. He said, “keep your legs up and spread Jennifer.” He grabbed my tits then he put a lot of his weight into my pussy with his cock. I could feel him slowly going further, my face was grimacing and he said, “You’re doing good, good girl…” He kept pushing and pushing, but only this time, his cock was actually traveling up inside me more. Then, the strangest and most erotic feeling came over me as I felt the weird sensation of a man’s balls resting on my bottom. “JENNIFER, WE DID IT.”
He kept himself fully inside me and put my legs back down, He started slowly fucking my pussy, all the way in and almost all the way out. “You like that sweetheart, I can tell,” he said. He was right, it was so wonderful. That feeling of being stretched is fantastic. After about 5 minutes of him pumping me slowly, he paused. “Ohhh fuck,” he said. I was like, “what?” “Ohhhh shit,” he says again. Then, he grabs my hips and starts fucking me really hard, my tits are bouncing everywhere and he jams his 9 inches into me and holds as deep as he could. I wrapped my legs around him and held onto to him. I’m loving it but its intense and I’m moaning, screaming a bit, and whimpering. Then I feel his cock jerking and pumping and he is sweating all over me, slowly moving his hips. “Ohhh fuck Jennifer, I couldn’t hold it baby,” he admitted. With his cock still inside me, he rolled to his side, he caressed me and I placed my leg over his hip and he grabbed my tits and we feel asleep. I woke up about 2 hours later. He pulled his cock out of me and cum started leaking out of my pussy all over my the inside of my thigh. I realized I needed to get home. Well, actually, he had to drop me off at a restaurant and my mom picked me up from there – as if I was the last one to get picked up from my group.
Now that he had got all the way inside me, he started teaching me new positions, but those stories are for next time.
Source: reddit.com/r/gonewildstories/comments/7ux4hi/fm_mike_finally_gets_all_the_way_inside
this was written by a boy