Late Bloomer Gets Lucky Ch. 09

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Jann takes some guy to her room.
4.1k words
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Part 9 of the 20 part series

Updated 06/13/2023
Created 02/07/2021
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There were no lights on at the neighbors' place and no car in the driveway so I was walking to the corner to see if I could catch Jann at the usual place if she was even in town for the weekend. It had worked well enough times that I would just go up to see and sure, many times I didn't meet up with her and saw nobody but it was my most successful system!

I was still 100 yards away from the corner and saw that there were two people walking. Sure enough it was Jann and she was starting down the lane with someone who wasn't Deb. I didn't recognize him and I ducked into the field behind a couple of trees long before they had a chance to spot me. There was plenty of light from the street lights but under the trees was very dark so I could see them clearly but they wouldn't be able to see me even if they stopped 20 feet from me.

I couldn't make out much of what they were saying but what I could was just small talk. Jann didn't seem to be as drunk as she was when I recently had encountered but she was hanging onto him and he had his arm around her. They passed and I thought to myself that this dude was going to get what I wanted tonight. I wasn't happy about that. As they started into the driveway I came out from the dark into the lane and followed them. As I got to the driveway, I stopped to listen and couldn't hear them so I went in toward the step.

From there I could see a little light coming from inside the house. I slowly crept to the bottom of the step and saw the low light flick on in Jann's room. Fuck! Instead of me getting Jann this other guy is going to have her all night. At this point I wonder if I might be able to look in her window but even I got on the second step I knew that I wouldn't be able to. That's when I noticed that the window is open. Over the beating of my heart I hear Jann breathing heavily and a little rustling. They have only been inside about 5 minutes and I clearly hear Jann gasp "Oh yes Bobby!" and some sounds of the bed moving.

I look around to see if there is anything that I can get up on to look in the window but there isn't anything. The sounds of the bed creaking get faster while Jann gasps and the creaking accelerates to maximum speed before I hear the guy grunt and Jann's excitement decline drastically. A minute or so later I heard her say "Where are you going?" He just mumbled something about having to get going and I could hear a little movement. "Bobby, don't go." Jann pleaded.

My god, this guy only fucked her for 2 minutes! "You don't have to go. Stay!" she almost begged. She continued to try to convince him to stay but I got the sense that she was not succeeding, so I climbed off of the steps and retreated behind their camper. I no sooner got behind it out of sight and the door of the house swung open, with the guy emerging and quickly descending the steps, then hurrying out the driveway.

I was pretty convinced that he wasn't planning to return so I carefully made my way back to the steps, listening for the sounds from Jann's window. I clearly heard Jann say "shit" before hearing the sound that the bed makes when someone gets up. The audible few footsteps as she left her room had me hastily retreating again. When she didn't emerge from the house, I crept around and saw that the bathroom light was on. The window was frosted so I couldn't see in but the exhaust fan was on and after a couple of minutes I could smell soapy scents so I was sure that Jann was in the shower.

My heart raced as I went back around the house and up to the door. I carefully tried it and it was not locked so I slowly opened it. After I was inside I could hear the shower and my heart was in my throat. My cock was about 3/4 hard and my adrenaline was pumping heavily. When the water turned off I stepped into Jann's room. My heart was pounding and my cock was throbbing while I waited behind her door. As I heard Jann coming up tne hall I thought that I would explode. I didn't know what I was going to do but I was beyond the point of no return. I unbuttoned and unzipped my jeans and my erection stood out and throbbed.

I felt that I was entitled to Jann's body and I was a little angry that she fucked this dude, if you could call it that. As unsure as I was about what was going to happen, I was pretty sure that I was just going to take her. I wasn't thinking straight but as she stepped through the door of her room toweling herself off, I rushed her from behind reaching around to cover her mouth with one hand and my other arm around her waist so I could somewhat try to steer her with my momentum.

Jann let out a little yelp into my hand and as she landed face down on her bed, I landed on her in a fairly controlled manner, not heavily, my cock pressed into her ass cheek. As I took my hand from her mouth she said "Bobby!" just as I was able to push her towel up to cover her head. She was shower fresh as I reached down and guided my stiff, throbbing rod into her cunt and sunk it in a couple of inches. "Oh Bobby!" she grunted as I pulled back then plunged into her again, this time sinking about 4 inches into her.

As I pulled back again, I felt the wetness of her pussy increase greatly and when I pushed in the third time, I sunk right to my balls. "Oh god!" Jann exhaled. When I pulled back and drove in her the fourth time it made a wet smack sound. She just had the wetest pussy imaginable. "I'm so glad that you came back Bobby." Jann whispered and I began thrusting into her firmly. She didn't move the towel that I covered her head with and just moaned and grunted with each stroke of my swollen pole.

I pulled her hips up as I straightened up a bit and stood. Jann instinctively pulled her knees up under her, elevating her hips to doggy height with her head and shoulders still down on the bed. While I continued to fuck her hot cunt, I placed my thumb on her anus which she immediately responded to with a loud gasp of an inhale. I then moved my thumb down to get some of her slippery secretions and spread the shiny wetness on her little butt hole.

As I pushed my wet thumb into her ass she gasped again "AHH!" and I started working it in and out of her tight hole opposite of the strokes of my cock in her hot cunt. Jann was really breathing heavily now and each of her exhales was a groan which accompanied each time I pushed my thumb into her ass. When I pulled my hard rod out of her wet box and removed my thumb from her ass, I put the engorged, slippery head of my cock against her anus and pushed. "No Bobby!" she yelped and moved forward while straightening her legs to flatten out. I braced myself well against her and moved with her so that the head of my cock was half lodged in her ass hole when she landed and was laying flat.

I once again made sure the towel was still covering her head so that she couldn't see that it was me. I put all of my weight on her back to pin her and I grabbed both of her hips to try to keep positioned right while I pushed my cock a little. Jann yelped "No! No! Not there!" just as the rest of the head of my rod disappeared past her tight ring. "Bobby! Stop!" she demanded again. I was just about to spring the surprise on her that it was me but I pushed another two inches into her rectum then I moved a hand under her and grabbed her pussy.

She was soaking wet as I began stroking her clit. The towel needed a little adjusting so I moved it to keep her covered and then worked that hand under her to grope Jann's big tits. "Stop Bobby..." she weakly protested as my cock invaded her tight tunnel. As I got my prick buried completely in her ass, Jann was still gasping out a protest with each of her exhales. I slowly pulled from her ass and pushed it slowly back into her as deep as I could and I felt a little pulse on the head of my cock.

I held my fuck stick buried to my balls in her as the pulsing squeezes started flexing on my hard tool. I kept rubbing her clit, then pushing three fingers into her wet box, then pulling out again to rub her clit. "Oh fuck Bobby! Oh fuck Bobby!" Jann gasped as her orgasm shook her.

This was the fastest that I had experienced Jann coming by far and faster than I could have even imagined that it was possible. I think that it was because she thought that this Bobby dude was fucking her ass against her will and because being forced turned her on the most her body was reacting even though consciously she didn't want him to be doing this. Her ass flexed on my hardness over and over in strong pulses and I moved my fingertips a little roughly over her slippery clit as she gasped and panted.

As her muscles stopped flexing, I started moving in her hot tightness again. I pulled back until just my knob was being held by Jann's tight ring and then I pushed back in slowly. Jann's breathing was erratic and heavy but slowing a little now that her orgasm had subsided. I took my hand from her wet pussy and wrestled it under her torso to grab her other breast and groped her firm nipples and flesh with both hands as I continued sawing back and forth through her tight anus. "Bobby, please stop." she begged, "Take my pussy. Not my ass!"

Jann's gasping and panting gave her away though. Her body was betraying her, physically testifying that nothing turned her on more than the act of being taken by force. I moved my hand back down to her cunt again. It was absolutely soaked, as was the bedding between her legs. "Please Bobby..." Jann groaned, "Don't fuck my ass." I started rubbing her clit again as Jann panted and moaned. "Oh god!" she exhaled as I began circling her clit, rubbing her wet pussy lips and fingering her cunt hole. "Take it out Bobby...take it out..." she begged as I continued pistoning back and forth steadily.

Then I felt a contraction again. A quick squeeze deep in her ass which was followed by stronger and more definite contractions. "Oh! Oh!" she blurted out uncontrollably as I buried my swollen, hard meat deep into her ass and felt the convulsions squeeze my shaft over and over. Another orgasm for Jann so quickly and the incredible stimulation along with the intense situation had me bubbling over the edge.

I began pumping in and out of Jann's ass just as her orgasm was peaking. "Oh my god!" she gasped desperately as my cock started jerking and spewing come in her tight heat. I thrusted and squirted and her ass squeezed and flexed. It was the most intense orgasm and I pumped sperm into her tight, flexing canal. My final flexes tossed out little squirts into her rectum and she whined again, panting "Bobby...take it out of my ass, please!"

"Jann," I said, whispering, "It's me."

"Wh-what?" she stammered.

"It's me. It's Kevin." I told her.

Kevin!" she immediately exclaimed, "Oh my god!" and she pulled the towel from over her head. "I can't believe it's you!" The relief was obvious in her voice.

I pulled my still erect cock from her ass and lifted myself up a little. Jann rolled over on her back and turned to lay on the bed instead of across it. She smiled as I moved between her legs and she hugged me. "Oh my god" she said "I thought you were Bobby! But it's you! It's you!" I kissed her mouth and she hungrily kissed me back as I lowered my hips to lay on her.

Her hand pumped my hard cock and she lifted her legs as she guided my knob right against her anus. I pushed it back inside her tight butt hole and she just beamed, "Yes. Oh yes!" she moaned as I began stroking inside her slimey, tight hole and my chest pressed against her soft warm breasts.

"God Jann," I told her,"I love fucking your ass." I started pulling back until just the head was inside her and then burying my pole back into her depths. The next three strokes were accompanied by Jann making huge, gasping inhales as I pushed my rod into her. Her cunt secreted so much slippery fluid that it ran down and continuously lubed my shaft. If there was ever a pussy as wet as hers, I would be shocked to discover it.

"Oh yes." she panted as I continued thrusting into her. "Fuck me." she urged. At that point I began pulling out completely and felt the elastic ring of her hole resist slightly on the fat head of my cock as I pushed back toward her and went balls deep into her ass. Jann pushed both of her hands down between us and began frantically rubbing her pussy so I kept my stroke the same.

Pull back until I was completely removed, then smoothly move back toward her, a bump against my fat cock head as it met her anus just before moving through it and burying my hard cock in her snug warmth. I did this stroke steadily about 20 more times and Jann gasped loudly and blurted out "Oh fuck!" as I felt that little pulse of her muscles on the head of my cock again.

I held my throbbing rod balls deep in her as she gasped and moaned while working her clit. The feeling of every flex and spasm of the muscles in her ass on my hard cock was incredible, and accentuated by holding it motionless in her tight tunnel while she rode out her orgasm. Jann's head jerked back and forth as the spasms of her rectum calmed in intensity and became less frequent.

She didn't gush when she got off but her cunt was so wet anyway. After the last of her spasms, Jann pulled her hands from between us and let her arms fall to her sides. She had her eyes closed and her mouth wide open while her breathing started to slow a little from the intensity of her orgasm.

I detected a little alcohol when I kissed her mouth and she kissed me back as I started slowly pulling my throbbing, rock hard cock from her snug grip. Normally, when a girl gets off, that's what sends me over the edge and I was not far from the edge. I had just about pulled completely out of her and pushed back into her as I felt the tightness around the head of my erection. I felt the pressure building as my cock throbbed while being sheathed in her tight sleeve again.

"Ohhhhh..." Jann whispered as I sunk back into her. Just as I got to full depth in her again I pulled out of her ass quickly with a short smack sound and moved just a bit then slammed my tingling cock into her soft pussy. "God, yes Kevin!" she whispered as I started fucking her cunt furiously, a wet 'CLUK' sound with every thrust.

I only stroked into her a dozen times when I felt myself going to come and I took my swollen, slippery erection from her soaking wet fuck hole and I quickly leapt off of her and stood beside her head. My right hand grabbed her hair and turned her face toward my jerking meat as my left hand guided my cock head to her panting mouth.

I shot two huge streams of come into her mouth before pushing past her lips and feeling her warm tongue on my pulsing, squirting pole. I reached down and put my hand on her soft breast as I controlled her head with my other hand. "Yes Jann. Yes!" I urged her as she sucked and swallowed my sperm, swirling her warm tongue around my swollen knob.

She just grunted "Mmmmph." every couple of seconds in between swallows. I pulled her head back a bit so that my cock was free of her mouth after the large squirts of my load were already down her throat, and I let a couple of small squirts land on her cheek and chin. Jann's eyes were closed and she tried clumsily to catch them in her mouth with her tongue out.

I pushed the head a little so that it was just touching her lips and as another small squirt tossed from the head Jann covered the end of my cock with her mouth. I moved her head back and forth on my knob and shaft until there was no more sperm for her willing mouth and when I pulled it out of her mouth and released her head she uttered "Jesus Kevin." amid her panting.

I climbed into bed again between her legs and pushed my slightly softened dick into her hot, wet cunt. As we lay there catching our breaths, I felt like drifting off and maybe having a little nap but Jann was slowly swiveling her hips and flexing her vaginal muscles giving a very unique sensation turning my softening cock into a hardening cock again.

I knew that I had to piss though so before I got back to fully erect I pulled from her hot cunt with a wet smack and got up to head down the hall to the washroom. It took me a couple of minutes to let my cock soften a bit so that I could urinate and afterward I returned to Jann's room where she met me at the door and also headed for the bathroom.

I laid down in her bed and waited for her to return. I could feel myself drifting off and nodded off once but only for a second or two. I could feel myself drifting off again and the next thing I knew I was waking up to Jann rubbing her tits in my face then kissing me with the faint scent and taste of minty toothpaste on her breath and tongue.

As soon as she would stop kissing me she would press her breasts in my face and steer her nipples to my mouth. Her warm soft tits and firm but not hard nipples felt amazing and I wanted to keep rubbing them and kissing them but she moved down to my hips with my stiffening meat in her hand and took my cock head in her mouth.

She kissed it gently and slowly sucked it into her mouth. Then she turned her head so that when she took some of my length into her mouth, the head pushed against the inside of her cheek and stretched it while she wiggled her tongue around my shaft. I was fully erect and throbbing now as she continued to lower her mouth over my rod and then take her mouth completely off of me, pumping my hard cock with her hand.

She planted a kiss on the head every time just before lowering her mouth on it again. Wow! It was unreal. I propped myself up on my elbows and watched as she continued sucking me like that placing kisses on my knob, pumping my shaft and taking my cock into her mouth another 20 times or so.

Jann would lick and suck at the head about every third kiss apparently feeding on the pre cum which abundantly flowed from my throbbing wand. As amazing as it felt, I felt the urge to change my stimulation and I sat up completely and reached for Jann. I pulled her up to me and turned to get out from under her. I put her on her knees and positioned myself behind her placing my fully engorged erection against her wet cunt and pushed into her completely right to my balls. "Oh yes!" Jann gasped as I sunk into her and slowly pulled out before quickly burying my tool in her hot, wet pussy again.

After a few times burying into her I began completely removing my hardness from her before mashing my swollen head into her warm, wet flesh again with wet sounds smacking every time the head was pulled from her hot hole. I had Jann's hips in my hands, slightly pulling her with every thrust into her heat but it wasn't long before I moved my left hand to center over her ass and pushed my thumb into her ass hole. "Oh god." she whispered as I began fucking her ass with my thumb.

The wet sounds of my cock smashing Jann's pussy filled the room and the tightness of her ass hole on my thumb were really turning my lust up to maximum. So I pulled my thumb from her smooth ass hole and as I pulled my cock from her wet cunt, I steered it to press against her anus. "No!" Jann protested, "Not there!" she said, but I knew this was part of her own little fetish of resisting and didn't hesitate. My cock was already 2 inches into her ass as she continued "Don't fuck my ass!"

As I pushed my rod another couple of inches into Jann's hot ass, I laid down on her back and reached under her, grabbing her cunt. "I'm fucking your ass Jann and there is nothing that you can do to stop me!" I told her in a serious tone fueled by my lust.

"No! No! Please don't!" she begged as I had already pulled back and begun pushing into her again. Jann continued to protest as I established a steady rhythm back and forth through her anus and into the hot tightness of her ass.

"Yeah Jann. Take that hard cock in your ass!" I ordered as I continued moving in and out of her exquisite tightness. "This is for fucking that other guy!" I said with a stern, angry tone.

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