Number One Fanby8teenholes©
This was a request sent to me by a fan. She provided me with a fantasy, and I just tried to make it a reality. I wrote this in a pretty short time frame, but I think it turned out pretty good. Thanks for reading!
I'm a terrible person! That is what I can't help but think right now! I always tried to make the right decisions and lead a wholesome path, but it seems like everything I do lately hurts the people I love most! I have always been a bit of a lost soul, but my boyfriend Todd has been so good to me, he was my anchor. He and I got together at a very early age, practically middle school! He and I rode the bus together, he was always very polite and sincere. I would fend off the bully's that would harass him daily. Todd was not the most socially skilled person that I ever met, but he brought me a certain amount of happiness. We dated all through school, I'd like to say he was the one responsible for taking my virginity, but I would be lying. He never pushed the boundaries, in fact it was me that normally had to take the lead!
The fact is, I lost my virginity the first night I experimented with alcohol. My best friend's older brother, Ron, bought us some wine coolers, they tasted so good! Robin ended up passing out leaving me all alone with Ron. Long story short I got really wasted and he took advantage of me. It hurt so bad, I bled everywhere, he did not seem to mind. He had no concern about my well being or pleasure, he took what he wanted. After he was done I cried myself to sleep on that cold basement floor. It was very traumatizing at the time, I was totally put off by sex. I had never even seen a fully hard penis before then, and I only caught a glimpse of him before he shoved it in me. All I knew was that it felt like he shoving a bus inside of me!
The guilt of that night weighed heavily on me for many months. I knew that I had not cheated on Todd on purpose, it certainly wasn't planned. He was still playing the part of the doting boyfriend and I couldn't shake my bad feelings. A few months passed and I was finally coming around, becoming very curious about sex. I was beginning to recollect positively and actually fantasizing about my first time as I lay in bed at night all alone. The details were becoming less traumatic, and definitely more hot. I would think about the way he smelled, or the sexy music playing in the background. Gone were all my fears and insecurities, my thoughts were now quite thrilling!
These thoughts would often lead to a session with a thick handled hair brush. I was really beginning to enjoy my new found sexualty. My girlfriends would talk explicitly about their liaisons and I wanted to have my own experiences! It was after yet another long study session that I made the first move on Todd. We had the house to ourselves, Todd's dad was on a two week business trip. Todd said his mom was out with his Aunt Mary, he did not expect her home until morning as it was not uncommon for her to stay all night at her sister's place when his dad was out of town.
We started with light kissing culminating into one of our hot makeout sessions. This is about as far as we had gotten in the last 6 years of our relationship, tonight, I wanted more! Todd was wearing loose fitting basketball shorts, I was shaking with anticipation when I reached through the waistband of his shorts to grasp his penis for the first time.
My whole hand covered it, it really didn't feel that intimidating at all! Todd moaned into my ear as I slowly began rubbing him up and down. My hand was getting wet with a sticky substance oozing from the tip. I wanted to investigate this mysterious organ a little closer. Todd was still sitting on the couch when I slid off onto the floor. I grabbed the bottom of his shorts and slid them down over his narrow hips. That is when I saw he was wearing a pair of Batman briefs. They looked so childish on his slender 18 year old frame. I had to bite my cheeks to keep from giggling. I remember Robin's brother was not wearing underwear at all the night he fucked me. I tugged his briefs down and finally got a look at the male anatomy.
It was really no big deal, Todd's penis was rather thin, and probably only as long as my index finger, heck my hairbrush was twice as thick as he was! He looked like he was in heaven, but he was still too scared to touch me!
I pulled off my tight fitting sweater revealing the lacy see through bra underneath. I was rather proud of my large chest, the girls would look at me with contempt, and I caught more than a few men checking out my rack when I wore my tiny bikini to the pool! I was pretty confident that I had the right stuff! I was shaking with nerves as I reached behind to pop the three clasps holding my bra together. I let the flimsy bra fall to the floor as I watched Todd's jaw drop!
He was obviously smitten with my twins! My thick nipples were hard with anticipation. The one pleasurable thing I remember from my experience with Ron was how attentive he was to my sensitive nubs. He was talking about how awesome my tits were as he roughly sucked and licked them. That was before he fucked me, I was sure that I could have climaxed just from the stimulation of his mouth on my tits.
"Wow Alexandra! These are marvelous! I always knew you had great tits, but the actual thing really out does my own fantasies!" Todd was grinning from ear to ear!
"Well I'm so happy you like them! You know you could have had these anytime! You need to just take charge Todd!" I continued to stroke him slowly with one hand, while the other was gently caressing my excited nipples. I pushed up on his knees slowly dragging my tits up his thighs then over his excited penis. Our mouths met once again as I sat straddling his knee. I was still dressed from the waist down. My school uniform skirt and white cotton panties were firmly in place.We were making out hot & heavy while his hands were all over me. He seemed very excited, and I just wished he would take a little more time with me!
His hands felt so good, even though they were a little sweaty and clammy. He was obviously nervous, I could feel him shaking with anticipation. He was grabbing my ass roughly, a little harder than what might have otherwise felt good. Todd had his hands under my checked skirt, he was fumbling with the elastic of my panties. He put his thumbs under the elastic of my panties and tried his best to peel them off of me. He was having trouble getting them over my hips, it was like his hands just couldn't coordinate with his brain.
I stood up in front of him and pulled them down. These weren't my sexiest underwear, I would have to remedy that soon. I let my panties drop down watching them puddle at my feet. I instantly jumped back on him, leaving my school uniform skirt in place. It felt very naughty to keep it on.
I whispered in his ear, "Do you have anything?" Even though my mother put me on the pill a year ago, I still wanted to be safe!
He looked back at me quizzically, "Wh.. what do you mean?"
"A condom silly! You will need some protection for where this is going next!" I was rubbing my wet pussy up and down his thigh and it felt very good as he manipulated my hard nipples.
"Sure, I think my dad might have one in his drawer! Let me go look!" Todd practically pushed me off of him to go hunt for a condom. I was alone in my thoughts waiting for my loving boyfriend to return. I took the opportunity to rub my hands down my flat tan belly, it was like every nerve was firing nothing but pleasure. I looked down past my tits at my furry pussy. I kept it neatly trimmed, it really made me feel like a woman! I know most girls shave it all, but I sort of like the way the my soft curls highlighted my womanly charm. I was starting to diddle my clit when I heard an excited run coming towards me. I closed my eyes. I wanted Todd to catch me masturbating, it just felt very naughty!
Suddenly I heard a loud crash! Todd had tripped on the rug! I jumped up off the couch to see him writhing in pain on the floor!
"Oh Todd! Are you ok??" I was concerned that our night might have been ruined! Todd was a very clumsy person, he was constantly tripping over his own feet!
"Yeah, yeah, I'm ok..." Todd sighed in pain, but he found his feet and bounded towards me. He had lost his erection, but when he got a look at me he firmed right back up!
'Did you get it? Did you find a condom?"
"Yup, right here!" He held up the gold foiled package proudly!
"It was the strangest thing, I couldn't find any in my dad's drawer, I found this under a bunch of stuff in my mom's drawer! I guess they don't want me snooping!" Todd was getting off topic.
"Ok, whatever, put it on and get over here!" I was getting antsy, my body was craving release! I had never experienced feelings like this before!
I watched as Todd fumbled with the package, I could clearly read the words imprinted on it, "Magnum, XL" in bold black letters. I didn't know that condoms were available in different sizes, I assumed all men were created equal. He finally just tore it open with his teeth! He pulled the slimy circle from the pack holding it up triumphantly. It looked huge! It was not even unravelled yet, but the diameter of the condom was at least three times larger than his rod! Todd pushed three fingers in it to get it unravelled. He then pinched his penis with his forefinger and thumb as he tried to put it on. The thin latex condom literally hung off his junk. He took a step forward to approach me. The condom fell off and landed on my thigh.
"I don't get it," said Todd. "I've seen my dad naked a few times, I never really thought he was that much bigger than me! Heck I caught him one day looking at porn on the computer, and I swear I was bigger than he is!"
Todd was getting a little red in the face, I couldn't understand why Mrs. Boyer would have such a condom in her possession, especially if Todd was bigger than Mr. Boyer!
"I have an idea!" I sat up and pulled out the rubber band holding my shiny brunette hair in a ponytail. I slid the ring over Todd's stuff to his balls. I had to wrap it three times before it would hold the condom on securely.
"There, that should do!" I was rather proud of my work, but Todd did look pretty silly. The condom was just so loose around him. I drifted off into thought about the dick that could actually fit in this thing! The thought really scared me! I was so lucky to have Todd! I certainly did not want to be injured again!
I leaned in and kissed the tip of his penis. I instantly had the taste of latex in my mouth, but I didn't find it all that bad. My girlfriends had all bragged about giving head, so I thought I would give it a shot! I was under the impression that all sexual activity should take place with a condom, so even though it didn't taste very good I tried my hardest to blow Todd.
He was moaning with approval as he tried to work himself into my mouth.
"Allie, you gotta stop that! I'm going to cum!"
I had only been sucking him for 5 or 10 seconds when he made me quit. It excited me to have him in my mouth, but it was very difficult to get over that taste!
Todd sat down next to me and we began kissing once again. He told me he needed a few minutes to calm down. Todd reached under my skirt and fumbled around the general area of my vagina. I took his hand and showed him how to touch me properly.
"Take me Todd! I want you inside of me!" I was ready for release, his fingers felt very good inside of me, but I wanted to orgasm with him deep inside of me!
Todd directed me to the floor of his family room, I spread my legs wide to allow him access. Todd got on top of me and tried several times to enter me unsuccessfully. I finally took control, grabbing his bagged penis, directing it to my hole. He pushed one time and was fully implanted inside of me. I was so excited that I could barely feel him. I could feel his little balls against my ass, so I knew he must have been inside of me! I was thankful that he didn't hurt me, I was looking forward to doing this more in the future!
Todd didn't move, he leaned down and started kissing me deeply once again. I wanted him to fuck the shit out of, just like Ron did that fateful night! That was not the sex Todd gave me... I was very close to my own climax as we worked on our second minute of sex. All of the sudden he grunted and groaned. I could feel him shaking and throbbing as he expelled his load into the condom.
Todd was on top of the world celebrating, he had no idea that he had left me high and dry. He kept kissing me and telling me how incredible that was. Todd stood above me, I could see the condom was now full of his cum. It barely filled the tip of it. Todd took off to go clean up, leaving me horny and alone on the living room floor. The second he was out of sight I closed my eyes and tried to finish myself off. I just could not seem to get there with the image of what Todd and I just did. I heard Todd returning to the living room, so I stopped what I was doing and covered myself with a blanket. He was dressing himself as I excused myself to the bathroom.
Todd must have forgotten to throw away the condom, it was sitting on the vanity. I took the opportunity to sit on the closed toilet seat. I inspected the condom unwrapping my hair band from the end. I tilted the condom and let the warm cum run over my fingers. It felt very unusual, a little sticky, yet it was runny. I brought my fingers to my mouth licking the sweet substance from them. The taste of his cum was not bad at all, it was actually pretty enjoyable! I spread my legs and started gently touching my excited clit. I then fully unrolled the condom, holding a piece of latex that was definitely over ten inches long! I closed my eyes and imagined a cock that could fill this out! It was only a matter of moments when I exploded in orgasm, convulsing every 3 seconds in complete ecstasy!
After I recovered I wrapped the condom in toilet paper and placed it in the waste basket. I washed my hands and made my way out to the living room. Todd was already playing a video game, it was some incarnation of Super Mario. He was completely engrossed as I got myself dressed. Every once in awhile he would pat my leg or give me a quick peck on the lips when the game was loading. I sat watching him not completely satisfied. I figured it could only get better from here!
"Hey Todd, I'm going to get out of here, I have soccer practice early tomorrow morning..." I stood up off the couch.
"Ok, are you sure? I thought maybe we could 'do it' again. My mom had a whole box of those condoms in her drawer!" Todd was grinning widely.
"No, I don't think so, I'm really tired, I better get going. How bout you go and buy some more tomorrow! And make sure they fit, I'm going to want much more of this!" I reached down grabbing his crotch while placing a kiss on his lips.
I drove myself home lost in thought the whole time. I was a little disappointed in Todd's performance this evening. I was expecting it to be some life altering experience, it just did not live up to expectations! The indicator light for my gas tank suddenly popped on. I drove to the nearest filling station, as I was standing there a couple on a motorcycle pulled up. They parked in front of the store. The woman pulled off her helmet and I instantly recognized her as Todd's mother! I did not recognize the driver. Mrs. Boyer was dressed about as sluttly as I have ever seen, she was wearing a tube top and mini skirt. The man roughly grabbed her hand and led her into the store. I was dumbfounded watching as she stumbled drunkenly behind in her spiked heels. She was normally so matronly and demure when I saw her around the house, I really had never seen her dressed in anything other than jeans and a frumpy top.
My tank was topped off, I was very curious as to whom she was with. I put on a ball cap that I had in my back seat to make my appearance a little more discreet. They were on the other side of the isles, looking in the beer case. She was hanging all over this guy, they kept stealing kisses. I was all the way down the other side of the aisle when the man grabbed Mrs. Boyer and started making out with. He placed his hands under her micro mini skirt and started grabbing her ass. He practically had her skirt pulled all the way up. Mrs. B had a really great ass! She was telling him to stop, but she never really put up anymore of a fight. She finally pulled herself free of him and they made their way up to the counter.
"Will this be all ma'am?" The black attendant asked, she was obviously annoyed.
"No, actually, can I get a 3 pack of the Magnum XL condoms?" Mrs. B asked nervously. She was trying to whisper, but because she was intoxicated it came out a little louder than she intended. She scanned the store with a drunken glare, I looked down for fear of being discovered.
"Oh we got a big boy here?" The attendant's attitude changed a little.
"I suppose, just the condoms and beer please..." Mrs Boyer averted her gaze to the countertop. The man was standing behind Todd's mother, I could see that he was massaging her ass right there at the checkout counter!
I heard a deep voice growl, "Hey, why didn't you grab condoms when you were home? I ain't payin for that shit! You know I don't like those damned things!"
"Well we had a scare last month! Thank God I got my period! It would have been difficult to explain to your brother! Hell, he got that damn vasectomy after David," Mrs. Boyer meekly replied. David was Todd's little brother, I stood in total shock at the news that she was fucking Todd's uncle Steve!
"I know, I know, I guess I have gotten pretty used to them," the man replied. "Pay for that shit, let's get out of here!" Steve threw down some cash and walked out the door. I could see the look of shock on the cashier's face! Mrs. Boyer paid for the things and hustled her way outside. She practically ran to Steve as he sat on his bike revving the engine loudly. I watched from the window as she straddled the motorcycle and gave him a peck on the cheek before putting on her helmet.
I wanted to follow them, but by the time I made it to my car door the taillight of his bike disappeared down the road. I was jealous that Mrs. Boyer was getting the action that I was dreaming of! Hopefully Todd would come around and be more forceful like his uncle Steve, but I knew in my heart that he would be just as meek as his old man.
The summer before we would start college was going great. Todd bought some condoms that sort of fit and things in the bedroom were getting better. Even the normal sized condoms were a little loose, but we made due. We would fuck each other almost daily, I was waiting for it all to become what I had always dreamed it could be. Todd's bedroom prowess improved only slightly, I would usually fake an orgasm just to get him to stop. After he was gone I would just take care of things myself. I did love him, I just wanted more in the bedroom, I felt very unsatisfied sexually. I knew there was more out there, I just didn't know how to go get it. I wanted to have amazing sex with my amazing boyfriend, I didn't think that was too much to ask!
Todd was an awesome boyfriend, if it wasn't for that I would have never tried to make it work in college. He would go to the ends of the earth to please me, and I would do the same for him. We positively adored each other, cheating on him never crossed my mind. I knew that he was the guy for me, and I could overlook his inadequate bedroom skills. He was not a very imaginative lover, we would almost always do it in the missionary position, it felt great to be submissive to him, but he wasn't exactly hitting all of my buttons.
I began innocently inquiring to Todd about his Uncle Steve. Todd told me all about the falling out between he and his dad. He was not really sure about the circumstances, but it had something to do with his dad's ex-fiancee. Basically his dad came home and found them in bed together, and he was never able to forgive him. He said that Uncle Steve would come to town every now and then to visit with him and his grandparents, but his dad wanted absolutely nothing to do with him.