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!
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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!