Late Bloomer Gets Lucky Ch. 03

On Friday night I was walking home from hanging out with friends. We were just walking around and having some laughs. A pretty dead night, but warm and quiet and those things are worthy of appreciating. As I was making the corner to my street I heard voices and when I looked to my right I saw 2 people walking. One of the people was Jann, Shera's older sister by 3 years.

Jann came home from university many weekends and was very social - such a contrast to Shera. She was shorter than Shera and thicker. She got lots of attention for her big tits. Shera was much better looking than Jann but Jann wasn't ugly, just unremarkable, so 'cute when she smiled' might be the best compliment of her facial appearance. She was not athletic and her physique was on the soft side, so in addition to her large chest, she had a round ass too and since her waist was small she had an accentuated hourglass shape. She would be considered average thickness if she were 5 foot 10 but she was 5 foot nothing.

I stopped at the corner and waited for them as they neared. Jann was with her friend Debbie who had been in the same high school graduating class. I noticed that Jann was laughing a lot and leaning on Debbie as they walked. We all greeted each other and I got filled in that they were at a gathering where Jann had a lot to drink. It was just a few hundred yards to her house down our dead end street and Debbie's route was to go the other way so I told her that I would walk Jann the rest of the way. "Just home though, right?" Debbie reinforced

"Home." I replied dutifully "Yes." So after brief goodnights Deb continued on and Jann took my arm as we headed down our street with her unsteadily walking and bumping against me.

Jann was very flirty with me and laughing quietly as we went. I was exchanging in conversation with her but I wasn't responding to the flirting at all, Suddenly she says "Take me to bed Kev." and laughs, to which I laugh as well. I start to think about how I would like to take her up on that and how I could just take her to the cabin down in the field. Jann always had a different boyfriend so I suspected that she had been having sex for years and she carried herself as such.

The rumors around town said that she put out and put out a lot. Anyway I couldn't really get around the thought of taking advantage of her when she was drunk so, even though I had already started to harden, I completed the task of delivering her to her house. I immediately started thinking about fucking her. How it might be, what her tits looked like, what her pussy looked like, just everything - including how I had just fucked her sister last weekend.

The next day I was in the yard and as I saw her walking up the street, I approached her. "How's it going?" I asked.

She laughed and said "I was so drunk last night!"

I replied quickly "Yes, you were. You were staggering lot and slurring when you spoke."

"Did I say anything embarrassing?" she asked. "Well..." I hesitated.

"What? What did I say?" she pressed.

"You told me to take you to bed." I replied flatly.

She acted surprised with herself and gasped "Oh, did I?"

"Yeah, you did. And I kinda wanted to but I didn't want to take advantage of you being drunk." I explained, somewhat sheepishly.

"Well, you did the right thing and thanks for walking me home. I needed the help!" she said, and as I told her it was no problem she then continued "Umm, if you see me drunk again," she paused "take advantage!"

"Uh...ok." I stammered and laughed a little nervously.

"Ok remember that." she said and giggled as she walked away and up the street.

This was not expected and I wondered about getting the chance again while kicking myself for not taking her to the cabin. It wasn't the perfect place but it was definitely workable. Damn! I kept thinking about how I missed that opportunity. My frustration got me really focused on trying to get another chance to get with Shera for another session, but it just didn't happen yet and this situation got me really turned on. If I could just get Shera alone I could take out my energy and lust on her.

That evening, I was looking for anything that I could manipulate into a meeting with Shera but the lights were off at their place and their car was gone. I was pissed at the inconvenience of it, thinking that if she was around that I could get something going. I might have been a little overconfident in that regard. Around 11 pm after thinking about fucking Shera for hours, I went out for a walk in the fresh air. Another warm quiet night and still no car or lights at Shera's house. Damn, that didn't go my way at all.

As I get to the corner I could hardly believe my eyes. Two people walking up the street. It's Jann and Debbie again. As they approach, I can hear the low laughter and see the wobble in Jann's walk. We greet and Deb says "You got this again?"

I laugh "Sure!" I say and we bid farewell. My dick jumps and swells and as we walk down the lane, Jann is really holding on to me. She's holding me like she needed me to stand and I feel her soft breast against my arm. She's laughing lowly as we move a little one way and then the other. "What would I do without you to get me home?" she joked.

"I don't know" I replied.

Then she said "And what about tonight?"

I asked "What do you want to know about tonight?"

Jann laughs a little and pauses. After a long empty wait, just hearing our footsteps on the pavement, she answers "I want to know if you'll take me to bed." My cock hardened more and I had to adjust my jeans a little. My heart was racing and the tip of my cock was poking out of the top of my jeans.

"I'll do whatever you want me to do." I offered.

"I thought that's what this meant" she said as she ran her hand over my bulge.

I was so excited that I would be able to make up for missing the opportunity last night so soon! For this to happen now was mind blowing after thinking that I might never get the chance. "Should we go in the camper?" I asked. They had a fancy camper in their yard.

"No, everyone is gone to my uncle's until tomorrow evening." she explained as she pulled a key from her pocket. I took the key so she wouldn't have to fumble with it in the door and her hand went to the front of my jeans rubbing my hard bulge as we took the last steps to the door. After getting inside Jann quickly took my hand and pulled. I smoothly locked the door again and put her key on the table as she led me to her room. I had been in it a couple of years before and she had shown me a porn magazine, pointing out things about naked guys' bodies. I guess it was a hint at the time but I didn't pick up on it.

Jann stopped me in front of her bed and clicked a dim lamp on in the corner before returning to me and, to my amazement, had my jeans down to my knees in about 2 seconds. She had my cock in her hand and was stroking it, looking up at me. I leaned down and we kissed hard as I put my arms around her. Man she was short. She was a full foot shorter than me! I could really smell the alcohol and taste it a little bit as we kissed and she pumped my cock with her hand. I was reaching down groping at her ass and our wet kissing sounds filled my ears. The wet sound from my cock head as she pumped it, could be heard over our wet kisses.

"My God, you really have a wet cock" she said and we kissed again before she bent down and licked my swollen knob. My god it felt good and she circled the end with her tongue as she kept pumping the shaft with her hand. When her hand would move down the shaft she would lower her mouth down with it and take my cock in her mouth. She almost lost her balance a few times and I tried to steady her. She attentively sucked my cock clean as she stood up and said "I'll be right back" before slowly staggering out of her room and down the hall.

A few minutes later I heard the toilet flush before the sounds of her slowly stumbling up the hall, steadying herself against the walls. While she was gone I had taken all of my clothes off and folded them neatly, setting them on a chair. I was standing facing her when she came through the door. "Oh my" she uttered and started removing her clothes. I reached to steady her as she dropped piece after piece of her clothing, stopping a couple of times to take the head of my penis into her mouth and when she was completely naked, I remained holding her as she lowered herself onto her bed. I laid down beside her and as I ran my hands over her big soft tits, I tried to look down to see her pussy but she was already moving down and I felt her mouth on my cock again.

"Oh nice" she said, seemingly talking to herself as she stroked my swollen rod and sucked the head. She pumped the shaft hard a couple of times and then put her mouth over the head and took a few inches into her mouth, swirling her tongue over the end. She took her mouth off of my cock and gave it a couple of hard pumps while saying "oh yeah" before taking it in her mouth again. It seemed like she wanted to suck all of the pre cum out of it, milking it with her hand and then consuming it as it appeared on the throbbing head.

Jann let go of my cock and threw a leg over me as I turned a little to lay flat on my back. Her breasts were hanging down in front of my face as she leaned forward to kiss my mouth. I reached my hands up and rubbed and squeezed her soft tits. She reached back and I felt her hand grab my throbbing meat, pulling it up a little. I felt warm wetness on the end of it and then, as Jann sat back, my whole cock was surrounded by her soft heat. "Ohhhh..." she moaned and started a slow bounce. "You can come inside me. I'm on the pill" she said as she kept moving her wet cunt up and down my shaft.

I was squeezing her soft tits and her round ass as she rode my rod. Her pussy was not tight like Shera's but it was wet and hot like Shera's. She was pretty intoxicated so her bounce was unsteady but with the rhythmic precision of experience and the way that she changed angles minutely to maximize stimulation told me that maybe the stories about her were true. Suddenly after fucking my stiff rod thoroughly she rolled off of me and onto her back. "I have the spins" she gasped as I got between her legs and buried my cock in one thrust.

I lewdly kissed her lips and stuck my tongue in her boozey mouth while I fully removed my cock from her at every out stroke, smashing her pussy lips with the big head of my cock as I sunk the full length back into her. She moved her hips expertly beneath my strokes as I buried my rod over and over in her. "Yeah. Fuck me." she quietly urged as the wet slopping sounds of our fucking took over. "Oh fuck me good." she said as I pushed hard into her. I stopped a moment and lifted Jann's legs, then I put my wet cock head against her ass hole. Before I could push, she immediately shifted her hips to the side and said "No. You can't do that. You can do anything you want but not that." I buried my cock in her hot pussy again and she continued talking as I stroked in and out of her.

"I have been with a lot of guys and I have never let anybody do that." she slurred "I decided a while ago that I would save it for the guy I marry." I kept fucking her wet box and she said "That will be the virginity that I give to him." As I plunged in and out of her, I thought 'nice story but what does that have to do with me?' sort of thing and I could see Jann turn her head to the side and close her eyes. She grabbed one of her tits and squeezed as I felt her change the angle of her hips. Her face contorted just a little as if she was concentrating and straining. As I continued to fuck her I picked up speed and she kept moving her hips beneath me, meeting my strokes. Her breathing picked up and she slurred "Don't stop! Fuck me! Yes!" as I continued my steady strokes.

As she gasped and pulled at her tits with both hands, I felt her pussy contracting and I covered her mouth with mine. She was coming and I continued to pound her hard as she panted into my mouth. I could feel the pressure building for me too and as I felt her coming down from the top of her orgasm, my cock started jerking and shooting inside her. "AAAH!" I gasped as the first of four big blasts of hot semen shot deep into her womb. I then quickly pulled out of her and moved up to her face grabbing a handful of her hair to help me steer my slimey soaking cock into her mouth. Her face twisted up a little as she ate the last few streams of cum from my jerking, spasming rod along with her own pussy juice.

As she smacked and licked me clean she said "You're a bad boy putting that in my mouth" her breathing still heavy. What a difference fucking Jann compared to Shera. Jann had no shyness or self-consciousness and was actively participating in the act even talking during the experience. I continued pushing my cock into her mouth and noticed that she had closed her eyes. Her breathing was just about back to normal and I was still gently pushing my cock into her mouth. My cock didn't get soft and when I continued to push it into her mouth she eventually turned her head away from it and moaned a bit.

I moved down and lined my cock up to put it inside her cunt again and I could see some of my cum running out of her. I pushed my cock back into her and started stroking. Jann didn't seem to react and as I kept fucking her I said her name "Jann." no response "JANN!" no response. Maybe a little moan as if she was nodding off. She was clearly very drunk and after some pretty heavy adrenaline from our sex and her orgasm, she may have been passing out, but I was still fucking her. I kept plowing in and out of her loose cunt and then reached my hands under her ass pulling it toward me as I buried myself in her.

I definitely understood why she always had a boyfriend. Her cunt was loose but it is hot and wet, she loves to fuck and she sucks cock so what's not to love? I put my middle finger against her soaking wet ass hole and circled a few times before pushing it inside. Jann moaned as I watched for a reaction. Her eyes were still closed and her head still turned to the side. "Jann." I said abruptly and again a little louder "JANN!" with no response.

Taking my finger from her ass, I lifted Jann's legs and pulled my cock from her wet fuck hole. I put the head against her ass hole and pushed a little, watching Jann's face. I thought I noticed her expression twist a little so I backed off slightly. I put my finger in her tight hole again and stroked in and out a few times. It was slippery, hot and tight and I pulled my finger out of her ass and rubbed her slippery anus in small circles. I moved my cock in and used my finger to help guide it to the right spot, then pushed the head of my throbbing member against her hot ass hole.

The pressure felt good but my cock was starting to ache for more stimulation. I kept watching Jann's face as I pushed and I felt the end enter a little. A little tension in her face but nothing major so I pushed again. Another inch of my rod was in her. I could feel my cock pulsate and throb in the tightness. I could feel my heart beat in my cock. I continued pressing my throbbing member into her bit by bit until about half of it was being squeezed by her tight tunnel, then I pulled out a little and rubbed some of the slippery wetness from her cunt onto my shaft.

I pushed against her asshole again and watched her face. A hint of tension seemed to be there again but I pushed and stopped then waited as my erection throbbed in her. I pushed again until I was fully buried in her ass. I started stroking very slowly, fucking her ass carefully. On about the tenth full stroke Jann opened her eyes and started gasping "AHH" each time I pushed my rod into her ass. Her eyebrows were a little furrowed and I stared into her eyes. After pushing into her hot depths a few more times, she slurred "I told you not to!" I pushed all of the way into her again and stopped with my throbbing cock pulsating.

"What are you saying Jann? You put me in there." I protested as I felt her tightness around me.

Her arms were up around my neck now holding on to me "What do you mean?" she asked confused.

"Just a few minutes ago you took your hand and pulled me out of your pussy. Then you guided my cock into your ass." I claimed. Her, mouth was wide open and panting. I could still smell the alcohol and I began stroking slowly again.

Jann complained between her panting "You have to stop. This is for my husband!"

I kept sawing in and out of her ass hole. "There's no going back now Jann. You put me in your ass so your ass isn't virgin any more. If it's only me who fucks your ass then it will still be a special gift for him." I assured her.

"OH MY GOD!" she groaned as she threw her head back. "Oh fuck..." she gasped.

"Your ass is so nice to fuck that your husband will be the happiest man alive." I told her as my engorged veiny pole impaled her. "I want to turn you over." I told her and as I pulled my cock out, the last couple of inches seemed to get ejected from her ass.

As I turned her, she got on her hands and knees automatically but as I pushed the head of my cock into her ass again she once again protested "That's for my husband..."

"Jann." I interrupted sternly "You put me in your ass. It's already done." I debated as more of my dick disappeared into her hot, tight sleeve. I reached under her and manipulated her pussy with my right hand as my left was squeezing and rubbing her soft breasts.

"Oh my ass." Jann moaned as I fully buried my rod in her tight rectum. So tight compared to her pussy but that pussy was so wet! Not only were her legs wet but she had a couple of slippery drops hanging from her slit. I straightened up and put my hands on her hips looking at her full, round ass as I pulled out of her tight hole, then plunged into her pussy all of the way. "Oh yes!" she said "Fuck me Kevin." and I stroked into her 2 more times before I pulled out of her and pressed the fat head against her ass hole, pushing it inside. "Oh my god!" Jann blurted out and I stroked into her tight ass as she panted and moaned.

"Yeah, let me fuck that tight ass." I hissed as I plunged into her again and again.

Jann had fallen forward only supporting her torso with one arm now as she rubbed her pussy, moaning and lowly uttering "Fuck my ass." every second stroke. I pulled out and fully sunk my rod into her pussy again and Jann seemed to be trying to catch her breath as I fucked four hard strokes into her. I pulled out of her hot soaking wet cunt again, put the head against her little pink button and pushed. My rod slid into her tight heat slowly and I quickly set into a long smooth stroke, sawing slowly in and out of her anus. Even as slippery lubricated as it was, her hole offered much resistance and I could see the edge of it raise when I would pull out of her as if it were trying to keep my flesh from leaving.

"Oh my god!" I heard Jann gasp as her body shook and I felt her ass contracting on my fat cock. Her hand was rubbing her pussy fast as she came and I fucked into her tight hole faster.

"Oh fuck." I exclaimed as my cock began to jerk and flex. Jann's ass was so tight that my ejaculation was a little painful so after the first 2 pulses, I pulled out of her ass and guided my spewing cock into her hot pussy.

I pumped 3 big streams as Jann urged "Yes! Fuck! Yes!" The heat of that big cunt was so comfortable and I convulsed as I deposited the last few squirts of sperm into her. I pulled out of her and she collapsed. I turned her over on her back and pushed my softening cock into her soaking wet, hot pussy "Jesus Kevin." Jann moaned and I just laid here between her legs and in the comfort of her big breasts as we fell asleep.