Will Blake was my best friend. We’d known each other since middle school and now, the Summer after graduation, we were headed to be rommies together at college. I was at Will’s as usual. He was taking a shower and I was waiting for him to finish and we were going out – hopefully to nail some fresh pussy. When new conquests were on the agenda we went across town to hang in the other high school’s area. We knew all the k**s from our school, but the k**s that went to Jackson High were not as familiar to us, thus great “trolling for trollops” as Will and I called it.
I sat on the edge of his bed leafing through a Sports Illustrated when Will’s mom passed by the bedroom door. She saw me and in her usual friendly manner popped in. “Hey Mike! Where’s Will?” He’s finishing showering Mrs. Blake, then we’re outta here,” I announced. “Oh? What are you young men up to this evening?” “Ahhh…just hanging out. We’re going over to the mall on the Interstate to check out the sights,” I told her not being too informative. She stopped, smiled and said “Trolling for trollops, is it?” I grinned a little embarrassed and smiled. “Will tells everything, doesn’t he?” I joked. She nodded. “Cute name you two came up with for your womanizing exploits.”
She looked nervous as she shuffled around Will’s room. “So, worked through all the girls from your school, huh?” I grinned and nodded. “So, what is it about you two that makes you such ladies’ men?” she asked. “Uh…just lucky, I guess.” She smiled and replied. “Well if I saw two such good looking young men I would be tempted, so you boys be careful. The Jackson High guys might not like you pilfering their women, ya know,” she cautioned. “Yeah, but we have guy friends there too, so it’s cool,” I smiled. She made her way back to the threshold of the door and turned. “Well, don’t let them things get ya in too much trouble,” she admonished, pointing and looking at my crotch. I was embarrassed and excited all at once and just smiled nervously.
Rita Blake was a long time fantasy of mine and her sexual mention got me stirring a little as I watched her fat ass as she exited the room. She wasn’t exactly a MILF, but she was way hot to me. I liked ‘em healthy, and she was oh so healthy for sure. Of course peer pressure being what it was I was f***ed to mostly date skinny girls, which was cool and all, but damn, something about big busted and a little chubby really got my motor running and Rita Blake was all chubby, big tits. And her face was gorgeous. She wore her blond hair in a short and flouncy bob. She walked like a sexual creature – graceful, feminine and alluring. I had lost many a dick load of cum picturing Rita in my mind’s eye as my cock exploded at the thought of her whenever she crossed my mind, which was every time I jacked off – at least once, sometimes up to three times a day.
Will came out of the hall bath in his boxers and dressed and we headed out for our evening of debauched conquests, or so we hoped. By about 11PM we had failed miserably in our mission. We’d hung with a bunch of k**s and talked shit to a couple of little possibilities, but nothing doing, tonight anyway. We drove back to Will’s house and went inside. Will’s mom was prancing around in her flannel PJ’s and considering it was June, that seemed too warm for me. She talked to us for a few minutes and we retreated to Will’s room to play PlayStation. By midnight Will was failing fast, having gotten up very early on that Friday morning. I was still wide awake as he tossed a comforter, blanket and a couple pillows for me onto the floor beside his bed where I always slept when I crashed at his house. Will passed out in about 5 minutes flat. I was still watching TV and when WGN showed Southpark at Midnight I was settling in to watch Cartman and the boys.
Will’s door was ajar a bit and I watched as Rita moved around the house doing whatever. I started getting a chubb watching her, feeling guilty at eyeballing my best pal’s mom like I was, but hey, whatcha gonna do, right? She seemed to be readying for bed so I went out and took a leak now before I made noise and woke her after she’d gone to bed. She smiled and said “Hey night owl! Will pass out on ya yet?” I nodded he was out like a light already. I then noticed she was staring at me with an unfamiliar expression on her face – she looked me up and down kinda like.
Then she shocked me when she said, “Wanna come sit and watch some late night TV with me?” I almost went stupid and said I was already watching Southpark, but caught myself and said “Sure, that’d be great.” She reached out and took my hand and she gently closed the door to Will’s room whispering “Don’t want to wake sl**ping beauty, now do we?” and she winked at me as she said it. She led me to the f****y room on the other side of the kitchen and we sat on the couch. She liked Southpark too and turned to WGN and needless to say I was surprised by that turn.
We laughed at Cartman and crew. “I’m gonna have a drink. Want one?” she asked. I watched her go to the cabinet and remove a bottle of Seagram’s Seven and get a fresh 7-UP from the fridge and make a mixed drink. “Seven and Seven is great! Want one?” I nodded enthusiastically. She made two 7&7’s and toddled back to the couch. I watched rather blatantly as her generous tits shook under her PJ top. She not wearing a bra as her nipples revealed, and her top three buttons on the top were undone and when she bent to hand me the glass I could see more cleavage then I knew existed in the world. She smiled and handed me the drink, and she clearly noticed my noticing her abundant tits. She smiled warmly and sat sort of sideways on the couch, her left knee against my hip.
We watched the last of the first of two episodes but I hardly noticed the TV show at all. I was preoccupied with fantasies about this feminine creature touching my hip. We downed the first drinks and she grabbed my glass and asked “Another?” Then she cocked her head to the side and asked “You are staying the night, right? No driving, right?” I nodded and said thanks “Mrs. B.” She smiled rather seductively and replied “Anything for my son’s good looking best friend.”
She returned with the two fresh drinks and sat down assuming the same position, this time her knee even more against my hip. We watched the show for a minute or two when she said “My feet are so sore. I was on them all day today.” I took my shot. “Want me to rub ‘em Mrs. B? I have been told I have great hands!” I eagerly offered. She looked at my right hand, lifted it, ran her hand along my palm and then flipped it over and ran her hand along the top. Her fingertips were almost electric. “Those are some nice hands Mike. Let’s see if you know what to do with them,” she said as she dropped my hand and straightened her legs. She leaned back on the arm of the couch and placed her pretty feet into my lap. He left foot was an inch from my growing cock.
I lifted the right foot and began to massage it gently. I worked the heel and then the sole. She cooed her joy. I then massaged each toe and ran my fingertips gently along the top of her feet, tracing the vein that stood prominently on the top from the ankle to the right side of her foot. She closed her eyes and sucked in air between her teeth. “God Mike, those hands of yours are dangerous,” she almost whispered. I gently placed her right foot back and sadly moved her left foot from next to my growing cock and did the same to it as I did to that foot. She let her head fall onto her chest and closed her eyes as I rubbed this foot. I was kinda getting into rubbing it when I glanced to the side back at her and she was staring at me. Her eyes were glassy, and she smiled seductively.
I dropped her left foot back to where it had been and picked up the right one again. This time I felt her move her left foot closer to my cock. By now I was half hard and the left side of her foot lay on my growing cock. I busied myself with the right foot again, this time spending a great deal of time kneading the soul and instep. Then I felt it. Her foot moved a little against my cock. Then it moved in the opposite direction a little. I gently slid down in the couch a bit so that more of my now almost hard cock could be reached and she obliged by letting her foot slide up and down the length.
I looked back to her and her expression said it all. She smiled a sexy little, flirtatious smile at me and said, “Amazing how good it feels when some is rubbing on ya…” then she a bit more blatantly slid her foot along the length of my cock. I looked back at her and that was it. I dropped her foot slowly and she decided it was now or never. “So, I feel like I need to return the favor Mike. Anything I can rub?” I slid down into the couch even more and placed her left foot directly onto my hard cock. She smiled a big grin and said “I can see you do need some massaging.” She turned and sat her empty glass on the end table. She then leaned forward and sat up. She stood and took me by the hand, and without a word spoken led me to her room, closed and locked the door.
She turned and it was all tongues and hands. I could not believe what was happening. Her huge tits were hot as they were smashed against my chest. Her hands were running up and down my sides as we kissed. Man this woman was so fucking hot I thought as we made out standing against the closed door. She then slid her hand along my bulge and purred “That feels nice Mike. Let’s get a look at that thing, shall we?” she smiled at me. She kissed my lips with a peck and opened my jeans. She looked down as she freed my cock and let it fill her hand. She used her left hand and she held my cock from the bottom and gently slid her hand up and down the underside of the shaft. She looked back up into my eyes as I towered over this short chubby woman and she whispered, “Jesus Mike, that’s one helluva cock in my hand.”
She fell to her knees and in one fell swoop engulfed half of it into her warm mouth where my tongue had just been. She put her hands on her knees as she knelt before me and worked my cock with her lips and tongue. And she looked up into my eyes as she did so. I was almost faint with pleasure, excitement and sheer joy. “Oh fuck, oh fuck, oh fuck…” I began to moan as it got good to me. She removed her mouth and spoke. I looked down. My cock was brushing her chin and lips as she said “I think my young stud is about to deliver me a present. I would love that-after all, a young stud like you can do this all night, right?” she hopefully asked. I smiled and said “All night,” She smiled and without touching my cock with her hands, swallowed me again. She looked into my eyes and worked my 7 inch cock.
She let it fall from her lips long enough to encourage me. “Fill my mouth Mike. Let me see how much you enjoy this.” That was about all it took. I took my hands and placed them on her head. My pants fell all the way to my ankles. She moaned in pleasure at my hands on her head and she cupped my balls as I began to cum into her hot mouth. I leaned back against the door and she sucked for all she was worth. She even almost took the entire thing into her mouth as I was shooting. I spurted too many times to count – besides, I was preoccupied and not counting anyway. I shivered as my load finished leaping into her mature mouth and the she withdrew all but the head and worked the rim with her lips and tongue. She was looking up at me and I was dizzy with pleasure. She sucked me off better then it felt when I jerked off.
She let my still at half mast cock fall from her mouth. She kissed the head and shaft and said “That was good!” She slid my shoes from my feet and pulled my jeans down past them so that I was naked from the wait down. She rose and kissed me more passionately than I had even been kissed. Still standing against the door she pulled my t-shirt over my head and here I stood, spent and naked before my best friend’s mom and my fantasy woman.
She whispered “Undress me Mike,” and I began to unbutton her PJ top. Four buttons later her shirt opened and revealed the most awesome tits I had ever seen. Not only were they very large, but they were perfect – at least to me. They hung a bit, but considering their size and weight as I hefted each glorious orb, it was no wonder. I slid her top from her shoulders and she kissed me as I squeezed both tits. She slid off her own bottoms as we kissed and now we were naked and smashed against each other.
She took me by my cock and led me to the bed. She sat on the edge of the bed and leaned down and kissed my stomach and licked my nipples. I pulled her by the arms to a standing position. I placed her on the bed on her knees facing me and she held up her magnificent tits for me to suckle and Goddamn if I didn’t suck them for all I was worth. She fed me first one, then the other nipple. Then she smashed them together and fed me both nipples at once. “Oh fuck Mikey!” she moaned. I began to nibble on her nips gently and she loved that. I bit a little harder and she was breathing very shallow and moaning. I took my left hand and let it gently brush her soaked labia. She began to quake. I let my fingertip slide over her clit, faster and faster until she held her breath and pushed down on my hand, but I withdrew it not allowing her to totally release.
She wanted more as I was only teasing her at this point. She dropped her right tit and grabbed my wrist and pushed and pulled at my wrist until she came with a squeal. I felt her gush onto my hand a bit and I had never experienced that, but I loved it. She broke from me and fell to her right side and pulled me by my hands on top of her. She was kissing me. Her tongue was making me insane with lust. She guided my fat cock into her very soaked but tight hole and I slowly pumped in and out. She grabbed my ass cheeks and pushed and pulled me to go faster, which I was glad to oblige her desires. In about one minute she was squirming and fucking me back really hard. I held myself above her and marveled at her tits as they fell to the sides of her chest and rippled with each thrust.
But what really got me was the way she looked into my eyes as I fucked her mature, 40 year old pussy. She was fucking me like she meant it. I pushed her to another two orgasms before I felt my own building. She guided me a bit more slowly. She pulled me down onto her and kissed me and my cum began to shoot into her cunt. She wrapped her legs around me and kept me locked there as we came in unison. I felt spent as my cum subsided. She whispered into my ear “That was the most incredible fuck I have ever had. Are you sure you’re only 18 Mikey?” I lay on her chest sweating and breathing heavy. She kissed my cheeks, neck and shoulders. I never lost my hardon and began to slowly pump her again.
“Ewww!” she purred, “there’s more?” I lifted my head and looked in her eyes and smiled and we began to kiss more passionately then even before. “Let me ride you,” she whispered and I rolled over, her still locked onto my cock, and she was now on me. Rita placed her hands on my shoulders and dangled her tits and nipples across my face. I licked and bit at each one in turn as she pumped up and down on my ever hardening cock. I loved watching her fuck me.
She would go between looking me in the eyes to throwing her head back violently as she came. After her second nut while on top of me she held herself on me with shaking arms as she pushed and slid back and forth against my cock. She was nearly spent from the solid one hour of fucking. I asked her “Can I cum on your tits Rita?” She hoarsely replied “Please Dear God do,” and I slid from beneath her. She lay on her back sort of, the four pillows propping her up some as she lay back against the headboard of her queen sized bed. I straddled her on my knees and she rubbed my cock with both hands as I held onto the headboard and she stared into my eyes. She was making me nuts.
She occasionally leaned forward and licked the head of my cock as she stroked it. It looked so big in her petite hands as both were wrapped around the shaft. As it was obvious I was getting close she used her upper arms to squeeze her magnificent tits together. Her nipples were distended. She stroked my cock with abandon as I began to release. “Oh fuck Rita…I’m cumming,” I muttered. I felt sweat rolling down my sides form under my arms as I began to shoot.
Rita squealed again as my first spurt shot onto her chin. She stroked me with expertise as about 5 more powerful spurts covered her tits, neck, shoulders and lips, some even landing in her hair. She then swallowed my cock and sucked me until I thought I would die from pleasure. She kept her full lips locked onto my cock, her gaze locked onto my eyes as she then took her fingers and scooped my cum from her body. She dropped my cock from her mouth and it lay on her cheek as she then sucked my cum from her hands and fingers. I still held the headboard to remain upright as she taunted me with her blue eyes and wanton expressions.
Finally my waves of pleasure subsided. I moved from straddling her magnificent chest. I let my feet fall onto the floor at the bedside and stood on wobbly knees. She was without doubt the most beautiful creature I had ever seen. She very sexily rose and stood before me, a foot shorter than I. She leaned up and kissed me as she looked into my eyes the whole time.
“My God Mikey…” was all she muttered as we kissed gently. Her hot body was pressed to mine and we slipped and slid as my sweat lubricated us. I looked over at the clock. It was almost 2:30AM. We had been at it for almost two hours since I started rubbing her feet. She let her hands slide down and held my ass cheeks tightly. “Did you enjoy that?” she asked like a little girl uncertain of the answer. “Fucking ‘A’ Rita. It was better than I fantasized about.” She grinned. “You have fantasized about me?” she asked, very pleased and hopeful sounding. “About a million times,” I adamantly replied. She grabbed me and kissed me again. “Well, just so ya don’t feel alone, I have been fantasizing about this for a long time too Mike.” “Honestly?” I asked, fearing she was playing tit for tat with me. “Oh yeah, Mike. You are so sexy and good looking, and you’re such a nice young man. It would drive me crazy all the time you spent over here with Will. In fact, to tell ya the truth, sometimes I would peek in when you were sl**ping on Will’s floor and I saw your bulging cock many times as it pushed against your underwear as you slept. I knew I had to have you.”
She looked at me a little unsure but I made it known that this was the most incredible experience of my 18 years and she was pleased by my praise and admitted desire for this 40 year old, slightly chubby divorcee. “I sure hope this happens again..and soon,” I sort of pleaded, having been shown nirvana and now feeling jealous at the prospects of it happening again.
Rita smiled and kissed me more. “It can happen whenever you like Mike.” I looked at this beautiful and incredible woman and let slip “I think I am in love with you.” She smiled a bit. “Well, that’s nice to hear, but love is likely a bit strong, no?” “Yeah, I guess, but I have dreamed of this for so long that now that it’s happened I want it to happen again and again.” She smiled up at me and kissed me on the end of my nose. ”Me too stud, me too!”
“Now scoot before Will wakes up and ruins our fun,” she reminded me. I put my clothes back on. She slipped back into her PJ’s and checked to make sure all was quiet. We could hear Will snoring in his bed two doors down. “Okay, it’s all clear Mikey.” I quietly entered the hall and turned to kiss her again. She smiled so lovingly at me and we shared one more passionate kiss. I slipped into the hall, back into Will’s room and took off my shoes, t-shirt and pants leaving just my underwear on as I laid down.
I had left the door ajar as before and about one minute later Rita came to the door and whispered. “See you in the morning, stud,” and she disappeared. I fell into a trance like sl**p only to be awakened by Will at 8:30 as he woke up and kicked me. “Get up man. Mom’s calling us. She’s made us breakfast."
I jumped up, groggy and out of it, but reveling in last night’s pleasure. I slipped on my jeans but nothing else and followed Will downstairs into the breakfast nook. “Good morning, gentlemen,” Will’s mom happily chirped. I sheepishly looked at her as she did. Will walked to her and kissed her on the cheek. “Smells great mom,” was all he said as he leaned in to kiss her. She looked over his shoulder as she hugged him and winked at me.
“You boys sit and eat,” she said. “After a hard night of young men’s dreams, I’ll bet both of you are ready for some eggs, bacon and pancakes. How about it guys?” We nodded and Will went to the fridge to get the milk out. Rita smiled at me as he turned his back and she mouthed “Morning stud!” I sat down and began to scarf my breakfast. I fantasized about last night and Rita. “Mom, is it okay if Mike stays again tonight too? We want to watch the baseball game tonight on the big screen in the den , is that okay?” Rita smiled and winked at me again. “Sure it is Honey,” she replied. “I like it when I have two big strong men in my house.”
I knew I would have a repeat performance tonight and began to day dream about that Heavenly experience as I ate. Rita took a seat between Will and I and remarked “Wow, you two fellas sure are hungry. Were you two up all night working or something?” she asked, an evil and knowing grin on her beautiful face. “Go ahead. Eat up men. Young studs like you two need your energy. Never know what today might hold.” She let her right hand brush my knee as she said it and my cock stirred again. Oh fuck, I thought, I am addicted to this fantasy woman, and smiled inside knowing how lucky I was. “Yes ma’am, I guess I might need my energy,” I muttered as I took another mouthful of pancakes dripping with real maple syrup. “After all, I had a HARD night,” I stressed.
Rita shot me a glance as Will’s face was buried in his plate. Her blond bob fell into her face as she looked at me and mouthed “You’re a very bad boy,” and smiled that knowing grin. How would I survive the next 16 hours until I could get my hands on this woman, I wondered in my horny head.