Late Bloomer Gets Lucky Ch. 15

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Jann submits to WE again.
8k words
4.68
5.3k
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Part 15 of the 20 part series

Updated 06/13/2023
Created 02/07/2021
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I was out mowing grass and looked up to see Shera walking up the street. She waved and I shut the mower down to talk to her. She slowed then turned toward me when the engine stopped and I began walking toward her. Her cut off denim shorts and a little halter top with tiny straps over her shoulders which were nicely tanned all contributed to a very nice package. My dick swelled immediately and her little tits under the thin material were like magnets to my eyes.

"Hi Shera. I haven't seen you for so long. How are you doing?" I asked.

"I'm doing well but very busy." Shera replied with a beautiful smile.

"I love your new curls!" I told her as her hair was styled and cut completely differently than it was the last time I had seen her.

"Thanks. I'm starting to get used to it." she said shyly.

"It looks great. I have really missed being with you. Would you want to meet me tomorrow night or on Saturday?" I asked.

Shera blushed a little and responded "I would but I am away for the weekend."

"Oh no." I said emphasizing my disappointment. "Well, hopefully some time soon." I added.

"Yeah. I hope so." she replied.

"Ok I should get going again here." I said motioning to the lawn.

"Ok. See you later." she sang and turned with a little wave continuing up the street.

Watching her walk away was adding fuel to my drive as her firm little ass swayed just a little back and forth. I finished the lawn and was very distracted thinking about sex and the extension of my Shera drought. I had a few other things to do in the yard and after finishing up I had a quick shower. I couldn't stop thinking about getting off after seeing Shera so I drove down town and checked in at Ann's office building.

I was really turned on thinking about redirecting my lust toward dominating Ann and fucking away my frustrations with her. My excitement built as I approached her office but there was a sign on the door with a notice of absense for the week. It was only then that I recalled that Steve had mentioned a swim competition that was on the weekend so I wondered if they might have just gone travelling for the days ahead of the event. Well, that was disappointing and really added to my frustration as I descended the stairs and left the building.

I thought about fucking Shera and Ann all night but I didn't jerk off and I awoke Friday morning still frustrated and in much need of release. I had a few chores to complete which kept my mind off of my sexual frustration a little but it had a really strong grasp on my thoughts and I could only shake it for short periods of time. I saw Shera and her parents depart in late afternoon and thought of Shera's sweet little pussy. My dick throbbed painfully.

As I laid about in the evening thinking about how great it would be to get with Shera again and about when that might be, I also thought about how hard I might fuck Ann on Monday. How would I get through tonight, Saturday and Sunday being this horny? Kelly was too new and I didn't have read on her yet. I liked the little distraction with Kelly but I wasn't sure if it was really her thing and I had called her but I got no answer. I was so horny that I couldn't even think straight.

I then wondered if Jann might be coming home for the weekend. Recalling how it was when I went into her house the last time was incredibly exciting and suddenly I forgot about Shera, Ann and Kelly. I wondered what I could do and I encouraged myself with 'maybes'. What if I got a note together and informed her that she would get a visit tonight? It sounded ok and if she came home it might work out fine. If she didn't come home, I would just abort the plan.

I prepared a note in the same block letters as before: "WE are coming tonight at 10:30 pm. Don't call anyone. WE have been watching you. Put a pillow case over your head and lay face down on your bed. All lights out except the lamp in your room and door unlocked. WE will knock 2 times then pause, 3 times then pause and then 4 times. That is how you will know that WE are here." I wrote 'WE' again at the bottom as if it were a signature.

I knew that when she came home on weekends that she normally arrived between 8 and 8:30 pm. I cautiously went over and put the note in the door handle at about 7:45. I went down the path in the woods just enough to be out of sight but found a spot where I could still view the door. I hated the thought that someone could come along and find the note.

My nerves were frayed and my adrenaline was high just thinking that someone else could show up before Jann or maybe someone would arrive with Jann. What could happen in those situations? Even if I recognized that it was someone else driving down the street, there was no way that I could get to the door and get the note without being seen. My heart pounded in anticipation. Each minute was torturous.

Finally a car was coming down the street. My heart was in my throat and I felt nauseous. My cover was good and I could see the driveway well but my nerves had my stomach bouncing and my mouth dry. I could see Jann get out of the car with a carryall and felt relief when nobody else got out. As Jann got to the steps she waved and the car pulled out with the horn sounding a couple of honks while it accelerated away. I was still nervous but in a different way now as I saw Jann with the note. She paused a few moments and her head swiveled, looking around, then she went inside. I exhaled and checked my watch which said 8:34 pm.

My nervous energy was through the roof and I took off down the path to go around the long way to get home undetected. I was going over possibilities in my mind and wondering what I should do next. About 9:30 I just decided that I would go and knock on her door so I walked over under the street light and up the steps. I reminded myself to just stay calm and cool as I banged on the door 5 times. Jann came to the door and said "Hey. What's up?" then retreated into the kitchen as I stepped in.

"Not much. How are you?" I asked. I noted that she looked at the clock and that she had a bottle of rum out, some mix and a glass on the table as well as the note that I had put in her door.

"I'm ok." she said as she sat at the table and poured a glass, then hit it with some mix. She grabbed the note, folded it a couple of times and stuffed it in her pocket.

"Having a couple are you?" I asked.

She laughed "Just a couple!" then she took a drink.

I moved up to her and reached out, groping her tit. Jann moved my hand away quickly. I said "I thought that you might be in the mood for a little company." and I reached out touching her breast again.

"Kevin! No!" she said abruptly as she pushed my hand away again and took another drink. "I have something to do tonight so you have to go."

"Are you sure?" I asked.

"Yes. I have to get going." she finished up and went to the door.

"Ok. I'll see you another time maybe." I said, as I made my way to the door and left, walking down the steps. I glanced at my watch which said 9:41. I had a semi hard-on and my adrenaline surged knowing that Jann was getting ready for the visit in a little while. I headed for home as my cock leapt again, lengthening and hardening.

At home I changed my clothes and collected the ski mask, some cloth strips, the duct tape and the blindfold. My cock was fully erect and throbbing and I felt the wetness on the end which had soaked my underwear that was stretched over it. I shifted my clothes and the head poked out the top of my jeans. I made my way back over to Jann's and checked the time. It was 10:29. I knocked twice, counted to 5, knocked 3 times, counted to 5 then knocked 4 times and paused briefly before pulling the ski mask on and quietly moving into the house.

The ambient light allowed me good vision and I could see that Jann had consumed a fair amount of the bottle that she had out. I slowly and quietly moved to her door and peeked in. There she was face down and a pillow case over her head. I moved slowly toward the living room and turned the tv on, adjusting the volume to what I thought would be too low to hear content from her room but enough to hear that it was on.

I altered my voice a little and said "I'll go in first." as if I were talking to someone. I returned to her room and started removing my clothes. My cock was so hard and it ached and throbbed, pushing the clear pre cum out of the head in little involuntary pulses.

Jann had a light shirt on and some shorts made from sweatpants material. As I got on the bed and the mattress sunk and moved with my weight Jann said "I did exactly what you told me to do." in a tense and pleading tone. As I straddled her, my swollen cock slapped down on her ass and made a wet patch on her shorts.

I pulled the light shirt she had on up to her neck and off of her. She was shower fresh and gasped with each movement or contact. As I reached inside the pillow case that was over her head, I applied the blindfold as well as I could while humping against her. After pulling the pillow case off of her head I made sure that the blindfold was secure and groped Jann's tits roughly while I breathed in the smell of the booze on her gasps before moving down and pulling the little shorts down and off of her.

Spreading her ass cheeks, I could see her wet pussy which I grabbed and sunk 2 fingers in. She spontaneously gasped as my fingers sunk into her soaked pussy and my cock lurched and strained. Damn! This slut loved to be raped! I stuck my face down between her ass cheeks and put my tongue flat against her little ass hole. Jann moaned loudly at the contact and I flexed my tongue against her wrinkled little pink circle a few times before straightening up and spreading her legs from behind. I sunk my aching cock into her soaking wet pussy with one hard stroke as Jann yelped "Oh God!"

I held it in her, pressing hard against her cervix and feeling the pressure on the head for a few seconds. Then I pulled it out all shiny and wet before placing it immediately against her ass hole. I had planned to bind her hands again but she seemed to be in 'surrender' mode which suited me fine because I wanted to get my cock in her as quickly as I could. Her head was turned to one side so I leaned forward and stuck my tongue in her mouth as she gasped. She tried to kiss me but I just lewdly probed and licked her mouth with my tongue.

I moved my hard tool around rubbing the fat, slippery head against her little hole. "Please don't fuck my ass sir. Please!" she begged and just as she finished, I straightened up behind her, and watched as 2 inches of my hardness disappeared into her little ass hole. She sounded as if she was still trying to inhale while her lungs were already full as I pulled back an inch then pushed into her hot tightness again. Jann continued to breath frantically as I pulled back again and two thrusts later, buried my throbbing cock in her ass. "Noooooo!" she whined as her muscles flexed and she started to come.

I was so worked up and her ass flexed quickly over and over on my throbbing dick. I wanted to come too and I could feel myself right on the edge but I kept buried to my balls in her, trying not to move just feeling her muscles flex on my staff repeatedly while she gasped and grunted "No." every few seconds. As soon as I couldn't feel any more contractions, I pulled back until my knob was the only thing still in her ass and then pushed the entire length of my fat cock back into her.

I stroked like that 3 times then pulled myself from her hot ass and got to my feet. I moved up beside her face and pushed my twitching cock into her open mouth as it exploded with streams of sperm. Jann gagged a little at the volume as squirt after squirt of sperm shot into her mouth and she swirled her tongue around while swallowing. I held her hair roughly and kept her head still as I moved my cock in her mouth with slow hip movements.

Jann swallowed every bit of the biggest load that I think I ever shot and after the last pulse of my orgasm, I pulled my hips back extracting my meat from her mouth. I steered my dick back toward her mouth and as soon as she felt a hint of my knob contacting her lip she opened her mouth wide and closed her lips on the shaft a moment later. She swirled her tongue around it in magical fashion as she enthusiastically sucked my fat rod.

I was very sensitive from having just come so I pulled my hips back again removing my manhood from her mouth. She gasped as her mouth reached for it and her tongue darted from her mouth as if she were trying to reclaim it but my hands held her head in place. Moving forward again, her mouth accepted my tool in her warmth and her tongue greeted it with a flurry of twisting and wet twirls.

I pulled my cock from her mouth again and grabbing the tape, I climbed on top of her again. As I pulled her arms behind her back and pulled the tape with the familiar sound of duct tape coming off of the roll, Jann pleaded "You don't have to restrain me. I won't fight you." So I put the tape back on the roll and placed it on the night stand.

"Just please don't fuck my ass any more. Use my pussy and my mouth but please don't fuck my ass." she begged. "I'll fuck and suck and swallow all night for you."

My dick lurched twice as she begged and as I pulled at her hips with my hands she bounced up onto her knees, keeping her tits pressed to the mattress and her head turned to the side. Her round ass displayed before me in the lamp light with her soaking wet pussy, her juices flowing freely from it. I smacked her ass - not hard enough to hurt her but perhaps enough to startle her.

I got off the bed and walked out of the room and into the hall. "Ok. She's yours." I said in a deep voice. I quickly returned and got on the bed behind her, grabbing both of her ass cheeks and roughly squeezing them while pulling them apart. Jann moaned as I put my cock head against her wet pussy hole and leaned against her, watching as my full length disappeared in her hot cunt. Wet smacking sounds from her sex accompanied her moans as I started packing my hard cock vigorously into her sloppy box all the while staring at her little ass hole.

I put my thumb against her little pink circle and continued stroking in her cunt. I noticed that she had reached down with her hands and was rubbing herself as I fucked her so I began withdrawing fully from her before leaning back in. I could feel her hands against my balls when I was buried in her as she was rubbing herself.

"Oh yes!" Jann gasped as I removed my cock from her before burying it in her hot cunt once more. I kept this stroke going for a minute or so then after pulling out I moved my thumb from her ass hole and pushed my fat cock head against it.

"No! Not my ass!" she yelped as the head pushed past her tight sphincter. I waited a moment then eased into her a little deeper. "Noooo..." she pleaded and as I pushed deeper into her again she complained "Why do you have to fuck my ass?" One more push and my cock was completely buried in her hot depths and I felt her muscles flex. "Jesus!" she gasped as her ass began flexing and pulsing on my hard, tingling erection and this time I couldn't hold on.

I put one hand on her head, leaning a fair amount of my weight on it and pushed her head into her mattress while I plunged my rod as deep as it would go in her convulsing ass. My hard cock lurched and the head pulsed while shot after shot of sperm pumped into her ass. "Oh fuck! Oh fuck!" she hissed as my invader pumped semen into her spasming hot tunnel.

"No." she weakly protested each time she breathed out as her ass and my cock flexed against one another. As soon as the big streams were finished, I pulled my meat from her ass and got to my feet again, quickly moving to her face. One small squirt landed on her arm before I could get my dick to her mouth but a split second later I had my pole positioned in front of her lips and her mouth engulfed the large purple head. "Mmmmfff." she grunted as her lips wrapped around my shaft and she started swirling her tongue around my knob as it deposited small spurts for her consumption.

I pulled from her mouth and turned her on her back quickly. She was still recovering from an intense orgasm and I was still closing one out. As I got between her legs a small squirt of semen landed in the crease of her bikini line and disappeared as I lifted her legs mashing them against her big tits. I grabbed my pulsing dick and sunk it halfway into her ass and Jann whispered "Oh god." There was enough of my semen in her ass to lubricate my entry so I was able to bury my cock in her with one more push. Immediately I spread her legs and pressed my bare chest against her tits.

I held my rod deep in her as my orgasm finished, pushing lightly against her. Jann was inhaling and whimpering "Not my ass. Not my ass." and her muscles flexed on me again as she began another orgasm. I leaned back as I felt the second spasm of her rectum squeezing my cock and I moved my thumb back and forth over her clit. "Oh my god!" she gasped as her ass repeatedly squeezed my wand. I thought that I might soften a bit after a couple of really intense orgasms but her ass squeezing me over and over kept me fully erect.

With her ass still flexing on my cock I began working it back and forth through her tight anus. Jann was still gasping deeply and her muscles were still contracting, though trailing off in intensity. I pulled my hard dick from her hot, tight ass and moved up beside her head again. I guided my cock into her mouth with one hand on her head and her lips closed snugly around the shaft as the head bumped into her lip on its way to her soft moist tongue. She covered my meat with her saliva as I worked in and out a few times and it seemed like she still wanted it in her mouth as I pulled it from her lips. From all appearances she had no reservations about ass to mouth.

I walked out of the room grabbing my t shirt and pulling it on. Moving down the hall a ways I said aloud "Ok, go on in. She's ready." in a different register than my normal speaking voice, and pronouncing things a bit differently. This was to add to the suggestion that there was more than one person there taking her. I didn't know if it was working but it was something that I decided to go with so I walked back into the room and carefully picked up my jeans. Jann was laying on her back still with the blindfold on breathing slowly, deeply, but quietly. Pulling one leg of my jeans on then a moment later pulling the leg out and dropping them to the floor In the quiet room it was very audible and as I watched Jann it seemed like her breathing sped up a little.

I wiped her saliva off of my dick with my underwear and moved toward her, placing a hand on her knee. Jann's inhale was more of a gasp as I pulled her leg a little to the side. Her pussy was soaking wet and her shiny juice had a sheen over her ass cheeks and the bed was soaked under her in a patch about a foot wide. I left the room and went to the bathroom, running the hot water and grabbing a face cloth.

After wringing it out, I returned to Jann's room and laid the hot cloth over her pussy and pressed it against her with my fingers. She inhaled loudly and I pulled my mask up and put my mouth on one of her nipples, licking at it recklessly leaving it shiny with my saliva before doing the same to her other nipple. I rubbed her crotch area with the cloth and then used the other side of the cloth on my hard dick, refreshing it a little before hanging the cloth on the rim of her trash can.

Leaning in to Jann's pussy, I pressed my tongue against her clit and sucked it lewdly. Her gasps and moans filled my ears as I tongued and pressed my lips to her cunt while watching the shiny, thick juice run slowly from her slit and down to her ass hole. Grabbing her head with both hands on her cheeks and jaw, I pushed my cock into her mouth. This time, I pushed deep until she coughed and as soon as she wasn't coughing, I pushed deep again. After doing this a few times, I climbed on top of her and buried my cock into her loose pussy.