The end of year party was supposed to be the one. The party that ends the year and my virginity. I was taking Lisa who was in my english lit class. The few days leading up to the party, Lisa had dropped strong hints that when she parties she likes to smoke weed and smoking weed made her horny.
I was prepared. I had begged my friend Kevin for help and he came through with five joints.
I picked up Lisa from her house and she lit up one of the joints as soon as she spotted them in the cup holder. By the time we reached the mansion where the party was happening, Lisa was giggling constantly and her nipples poked visibly in her tight top. Their view had me hard already, I could barely hold my self from reaching out and grabbing those magnificent orbs of hers. She was clearly not wearing a bra and her jugs moved freely under her tight clothing.
“Ooh, there is hunky Josh!!” Lisa squealed as we crossed the front door into the large foyer. And just like that, I lost my date. I watched stunned as Lisa ran to Josh, jumped and wrapped her arms around his neck and legs around his waist, a second later had her tongue down his throat. Stunned, I watched as she dragged him up the circular stairs to the second floor where the bedrooms were.
Having lost my prospect for sex, I went to the liquor area and proceeded to get smashed for the first time of my life.
“Hey there Jake!”
I turned to the voice behind me to find a disheveled Lisa smiling at me.
“Have anymore of those good joints?”
I’m sure I badly slurred the ‘fuck off bitch’ that I spat at her, and I turned and headed for the door. I abhorred the idea of losing my virginity to sloppy seconds with a slut that could do such a thing to me.
I was about to get into my car to drive off when Kevin stopped me and shoved me into his car.
“I don’t think you should drive as you are buddy.” Good Kevin saving my ass again.
Next thing I knew was Kevin pulling me out of his car and guiding me to my front door.
“Sorry buddy, gotta go, Janey’s waiting for me back at the party.”
It took a while to find the key hole, but I finally managed to open the door. I don’t even know how I got to my bedroom, but I was very aware of the ache in my balls. I had been so ready for this night to be the night of my dreams. The dream that had eluded me so far. The dream of being welcomed into a willing woman’s warm and slippery depths. Lisa’s honey pot was tonight’s promised land. But I was denied at the last moment with no new prospects in sight.
I hadn’t masturbated in a week and my testicles were bursting with multiple loads that I had readied for that fucking whore.
As I laid on my bed, the ache in my balls wouldn’t let me even pass out despite all the alcohol that saturated my system. I had to get some relief.
I vaguely remember unzipping my jeans and and pulling my painfully hard cock out. I vaguely thought about whiskey dicks and how they’re not supposed to work, and I figured that I hadn’t had enough to stay limp.
It took a while to blow my load as my hand coordination sucked and I couldn’t get a good rhythm going, but blow my load I finally managed.
Man was it a load. I felt all wet after, my shirt, my arms, my jeans, even my face got some spatters of cum.
The relief was great and I fell into the alcohol induced coma that I needed.
The light was painful on my eyelids. I turned on my other side to avoid the brightness pouring thru my bedroom’s window.
Bit by bit my brain fog dissipated, and alertness slowly crept into my head. I felt a little odd. I couldn’t put my finger on it until I finally opened my eyes.
First thing that struck me is that I didn’t have a headache. I had drunk myself silly the night before and by all expectations, I should be severely hungover. But I wasn’t. No headache at all.
Second, I was sure that I slept in my tight jeans, but I wasn’t wearing tight pants!
I slowly got up to find that I was sleeping in my boxers as usual but they were clean, no sign of dried up cum anywhere except my shirt. I kept trying to figure out what happened, but I couldn’t remember a thing after my mostly blurry masturbation session last night.
No jeans, no cum crust on me mostly. What the hell?
I got up and went down to the kitchen to find the house empty. Mom and Madison my older sister were nowhere to be found. I figured that since it was Saturday that they were probably at the mall doing their weekend shopping, dad was of course golfing as is his habit on Saturdays.
Somebody must have cleaned me up sometime between last night and this morning. Somebody had removed my jeans cleaned up the cum from my face, my arms and my dick. Somebody had cleaned up my dick! That idea floored me when it came to the forefront of my thoughts.
With two women in the house I couldn’t figure out who had done it. While mom loves me, she was strict enough to leave me to learn my lesson. My dad wasn’t the nurturing type and he wouldn’t even check on me at night, not since I turned eight.
My older sister and I weren’t particularly close and a lot of times we didn’t get along. Why would she take care of me?
It was a toss up between mom and Madison and neither was more likely to do it. I could believe that some fairy god mother did it than either of them.
I fried myself some bacon and eggs for breakfast, and filled my belly with something other than liquor.
I spent that day lounging around, watching TV or browsing the net on my phone. It was late afternoon when everybody came back home. Mom had brought some fried chicken with her for dinner, and set up everything as efficiently as she usually does.
At the dinner table, I tried to figure out my benefactor to no avail. Everybody, mom, dad and Madison behaved exactly as they usually do. Madison was perfectly normal as we did the dishes like we do after every dinner. No glances, no smirks, and no clues whatsoever to help me figure this out.
I went to bed that night as clueless as when I woke up. I didn’t dare ask, lest I tip somebody onto something they don’t need to know.
However, considering all things, mom seemed the most likely person to have taken care of me, being my mother and all. But the uncertainty bothered me.
Not knowing bothered me more every day until it became unbearable, I had to know and started thinking how to find out.
At the end, I figured the only way to know was to set up the same circumstances and hope to catch whoever it was red handed so to speak.
Three weeks after that first time, I pretended to go out and pretended to come back totally drunk. I spilled some scotch on my face and clothes to make myself smell appropriately. I stumbled into the dark house after midnight and proceeded to my room where I opened my zipper and masturbated until I jizzed all over myself like before.
And I waited with closed eyes.
And fell asleep, only to wake up the next morning in the most miserable shape. I got up, cleaned up myself and thought things through.
I hurt my head thinking so hard and came to no clear conclusions.
At the end I figured that somehow the circumstances weren’t the same and something must have changed, or that I imagined the whole thing.
Three weeks later, I came to no better plan. I still had no clue what to do differently.
So yet again, a week later, I played the self-abusing drunk and fell asleep covered in my own cum.
It could have been a dream, but the sensation was intense enough to pull me out of middle-of-the-night sleep. I kept my eyes closed while I felt my jeans being pulled down my legs.
I could detect light on my eyelids, so I didn’t think it was safe to simply open my eyes and see who it was, so I kept them shut.
Once my jeans were off, my boxers were also pulled off.
“Such a waste.” I heard Madison’s voice whisper.
I almost jumped out of my skin when I felt something wet cleaning my right hand of my cum. Wet, warm and rough, like a tongue. Madison was licking my cum off my hand!
Next thing I knew, the tongue moved to my cock and licked it clean. Madison even sucked my limp dick hard as if trying to extract any bit of cum that remained in my urethra. I started becoming hard. No whiskey dick here.
I heard Madison emit a questioning ‘Mhm?’. I guess the previous time I didn’t get hard again as she cleaned me up.
I didn’t know what to do. Do I open my eyes and ask her what she’s doing and why? Or should I pretend that I’m really passed out? What if confronting her freaked her out?
As I thought about what to do, I noticed that Madison has been sucking my cock all along. She was giving me a blow job while I was ‘passed out’. I was now fully hard and about to blow again.
I’ve never had a blow job before. I’ve seen plenty of porn, but yet to experience it. One thing for sure, Madison seemed focused on sucking hard on the tip while jacking the rest of my cock fast. The feeling was incredible and made me blow my load no more than a minute after I first felt her lips on my noodle of a cock. Yeah, being a virgin can get you to go hard and blow in short order when getting sucked for the first time.
It was incredible. The feeling of Madison’s lips on my cock was heavenly. She didn’t let go and kept squeezing my cock in a milking motion until no more spurts were coming forth.
I felt my sister letting go of my cock.
“Nice! Tastes best fresh.” I heard a whisper.
Next thing I felt were my feet being pushed into clothes; Madison put fresh boxers on me and left the room.
I don’t know what Madison was thinking, but didn’t she think that when I woke up I would know something happened? Did she really believe that I wouldn’t even remember jacking off? Wouldn’t I wonder who did what she did to clean me up?
Something was going on with Madison. I loved how she sucked my cock and I wanted more of course. But I didn’t want to have to go through this every time I wanted a blow job. But I was at a loss how to go about talking to Madison about what happened and to convince her to do it again but with me being awake and enjoying it.
Before I had a chance to move, I heard my sister coming back. I closed my eyes and remained as she left me. I almost jumped when I felt something being slipped between my lips and sweet liquid poured into my mouth. What the hell? Madison was feeding me a sports drink with a squeeze bottle. I swallowed and kept swallowing as my sister kept squeezing more liquid into my mouth. So that’s why last time I didn’t have a hangover when I woke up. I wasn’t dehydrated at all. I was struck by my sister’s thoughtfulness. She must really care.
I thought it would never end. But eventually, my sister pulled the bottle’s tip from between my lips and left. I waited for a while without moving just in case she came back. I was only sure she wasn’t coming back when I heard the shower running in the common bathroom.
Sleep took a while to take over me despite blowing a load twice. My mind kept running over what happened and what I should do. I only fell asleep after I formulated a new plan.
Only one thing could explain what Madison did. It’s irrational, but it’s the only logical explanation. Madison likes cum enough to even lick it off her own brother. Nothing else explained what happened. Like our mother, Madison was a good looking redhead with a curvy body to die for, she didn’t need me to get some cum. She could simply say ‘yes’ to any one of the countless guys that usually hit on her wherever she went, and she would get drowned in cum.
So I thought if she liked it so much, she might not mind getting directly from the source with the source’s cooperation. She didn’t have to wait until I’m unconscious to get something she liked.
The plan was simple, offer Madison a chance to get what she wants, as often as possible.
So the next Friday, I waited for my parents to go to sleep, laid in bed in boxers with the tip of my hard dick sticking out of the front, and pretended to sleep while leaving the door cracked and the light on.
I was dozing off when I heard the toilet flush. I paid close attention to noises and hoped that Madison would look into my room.
The bathroom door opened and closed and I thought I heard footsteps stopping in front of my door, but nothing further happened. Too many seconds later, Madison’s door opened and closed.
Madison must have looked in and decided not to do anything.
The Friday after, I did the drunk masturbator again.
Sure enough, Madison licked me clean and sucked me off to a toe-curling orgasm that almost made me cry out and blow my cover.
I tried the sleeping with a dick out thing again and again got no results. I guess Madison needed the assurance that she wouldn’t be discovered in order to get what she craved.
I didn’t want to do the drunk thing forever so I decided to confront Madison.
I gave her two weeks break and tried again and sure enough, clean up service happened.
The next morning, I woke up early and waited for a sign of life from Madison’s room. As soon as I felt that she was awake I headed to her room.
“Madi, did you go into my room last night?”
Madison’s face started flushing and she seemed hesitant.
“No, why would I?”
“Last night I came home drunk, and I was sure that I was in a mess, but this morning everything was fine. Did you help me clean up last night?”
Madison’s face turned almost purple. “No, I didn’t. I don’t know what you’re talking about. Leave my room please, I need to get dressed, we have shopping to do.”
“I’m not upset or anything. If anything I’m very thankful to whoever it was.”
“I don’t know what you’re talking about. Just fuck off.” And she got up and stormed out and into the bathroom and didn’t let me finish.
Well, that went as well as I expected.
That day afternoon, Madison avoided me most of the time. When she couldn’t, she wouldn’t make any eye contact and when I caught her glancing at me, she turned and blushed a little.
I tried to talk to her again with the same results, but she didn’t flush as much. She got used to denying what she did.
A new tactic was in order.
To figure out if my theory was correct, I decided to test Madison. So before going to bed, I masturbated into a clear glass and brought it to her room. I knocked and when she said come in, I opened the door to find Madison in bed already with a book in a hand.
“Since you seemed to like it, I thought I would offer you a gift.” And I put the tiny glass on her night table, and turned and left before she really knew what was in the cup and react.
It was a huge gamble. Madison might not react as I expected and might tell mom, but I was hoping that she would be afraid of me telling mom what she had done, despite no evidence in my hand.
Nothing happened that night.
I was apprehensive the next morning as Madison might still tell on me.
But nothing happened that day either.
I felt great relief by that night. If my sister had decided to tell mom or dad, she would have done so by then.
I didn’t know what she had done with the cup of cum, but whatever it was, she wasn’t telling my parents about it. So I felt somewhat safe in repeating the offering.
And again, nothing. Madison was as opaque as ever. In front of my parents she behaved perfectly normal. As in no hints of anything different ever happened. She avoided me mostly, but behaved normally even though I gave her my cum twice. She definitely was a good actress; she had me baffled.
But, logically, since she didn’t snitch and didn’t really tell me off about my gifts, I could only deduce that she didn’t mind them.
So the next time I brought her a small glass of cum, but I hadn’t put all of my cum in the cup. I smeared some on my still-hard cock and wrapped my naked midsection with a bath towel before going to her room.
As I brought the glass inside, Madison rolled her eyes at me, while having a questioning look in her eyes, maybe about my nudity.
“Haven’t you given up yet? What makes you think I want these?” she said as I didn’t leave right away.
“Well, I thought I would do something better and offer you some fresh from the source.” I said as I approached her. I opened my towel and saw her eyes dart to my throbbing cock.
I felt really confident that this would work as she hasn’t screamed at me yet.
“There is some fresh here for you.”
“What the fuck are you doing?” She hissed.
“Giving you something you like.”
“Who said I like this?”
“Your actions.” I said as I rotated my waist and swung my dick back and forth in front of her eyes.
“Come on, you know you want to.” I said as I observed her eyes follow my cock left and right.
“Get out of my room.” Madison urged me weakly.
Instead of doing what she asked, I approached even closer so that my legs touched her bed. Now my cock was within a foot or so of her face.
“Come on...” I said quietly as I squeezed a dollop of cum that I had left in my cock.
“Fuck you!” Madison spat quietly while leaning over to lick the drop off the tip.
Yes!! I won! Finally, I got her to openly lick my cum.
“Want more? How about you suck a load directly?”
Without a word Madison reached for my cock and pulled me closer. I climbed onto her bed and stood on my knees in front of her as she performed her ultra efficient blow job on my very appreciative cock.
I didn’t last more than two or three minutes before I unloaded a fresh batch of cum into my sister’s grateful mouth. Once she finished swallowing my load she went on to clean my dick thoroughly using her tongue. She even pulled it up and licked my balls for any trace of cum.
“That’s more like it.” I said as she let go and wiped her lips with the back of her hand.
“Now get out.” She said dismissively.
“Not yet.” I said as I sat down where I was kneeling a moment before. “Can you tell me why you cleaned me up so nicely those few times that I was drunk?”
“I don’t want to talk about it.” Madison said as she opened her book to resume reading.
“I do. I want to know why you did it. I liked what you did for me and I would love to help you back. If I knew what you liked, then I could offer you something in return.”
I waited patiently for more than a minute for her to reply. I could tell that she was thinking about it.
“Well, if you must know, I love the taste of cum.”
“That’s it? You like the taste of cum? You love it enough to get it from me your brother!”
“Yes. I know, I have a problem.”
“What do you mean a problem?”
“Well, it’s a problem when I can barely contain myself from dropping to my knees in front of any good looking guy at school and offering to suck him off just to sate the craving that I feel in the pit of my stomach every day.”
“Yes, that bad. It’s torture to keep my reputation clean and not be known as the cum queen of Johnston High.”
“So you sucked me off when you had the chance?”
“Yes.” My sister said as she dropped her head and fidgeted with the cover of her book.
“Well, I’ll tell you what. I loved what you did for me. I loved your blow jobs.”
“Really...” She stated sarcastically.
“Yep.” I answered earnestly despite the dripping sarcasm. “I’ll offer you a deal. How about you come to me whenever the mood strikes you and get what you need? This way, I get an amazing blow job, you get a load of cum and you keep your reputation in school intact. It’s a win-win.”
“I’ll think about it.” She said dismissively.
I was sure that Madison would take me up on the offer.
It took only two days for things to go forward.
I was in my bedroom getting ready for the night when there was a muted knock on my door.
The door opened and Madison came in wearing a nightgown while furtively looking behind her.
“I don’t want to risk mom finding out that I’m here. She might suspect something.” Madison whispered.
“So, how are we going to do this.”
In answer I walked back to my bed and simply pulled my boxers down. My cock had already become hard with anticipation.
I sat back against the headboard and spread my legs leaving plenty of room for Madison.
With a smirk on her face, my sister climbed on the bed and got to work quickly. In less than two minutes I had come very hard in her appreciative mouth. She made sure that she got every last drop and then got up and went to the door. She listened for any movement outside and when she was sure no one would see her, she slipped out quickly and went to her room.
I on the other hand just sat there and marvelled at my unbelievable luck.
Things continued in the same manner for few weeks. Madison would come to my room once every other night, gets a load of cum and leaves me fairly satisfied. I didn’t have to masturbate anymore, and I sure didn’t want to.
Bit by bit our relationship evolved. When we were in close proximity I couldn’t help touching her. Subtle touches, from her butt at the beginning to her tits. While she resisted mildly at the start, she got used to my touches and didn’t show any negative feelings about it. On the contrary, most time when were together, she would stand closer than how she did before this started.
Also, things changed in our routine gradually. The first change I noticed was Madison not wearing a bra when she came to my room. The sway of her large tits was very nice and enticing.
Second change was that Madi wasn’t trying to be as efficient anymore. Her efficient blow job was for her to keep my tip in her mouth locked by her lips right below my glans and she would rotate her tongue around the sensitive bit while applying strong suction and jacking the rest of my cock with her hand firmly.
Bit by bit, she started taking me deeper into her mouth, and slowing down. She would be playful and varied her technic. One day she even pinched the base of my cock when she felt me about to come to delay the end.
As Madison changed her action, I started changing and advancing our activities too.
I started reaching inside her top and pinching her nipples and kneading her tits.