Linda and Me
By Stevesaint
Used by permission of the author’s estate
© 2006 STEVESAINT
How did I get into this? I couldn’t blame my mom, though she did play some part in it. She’s her friend, after all.
My mom’s new friend Linda Fowler was over for coffee when we were introduced. My name is Richard—don’t call me Dick—though I know from seeing the other guys’ in the locker room that mine is pretty special. Even my mom unbelievably made a comment to me a few years ago (when she saw me naked after a shower) that I was “hung like a horse” and I “certainly didn’t take after” my father. My dad left us quite a long time ago for another woman, leaving mom to raise me alone. I think she’s done a great job.
“How old are you, Richard?” Linda asked, looking me up and down.
“I’m fifteen.” But my dumb-ass mouth couldn’t say anything more.
While Linda was “appraising” me, I checked her out as well. She looked pretty good, not nearly as old looking as my mother, with nice dark hair and a good body. Not big in the breast department, but not flat either.
“Nice looking boy you got here, Monica,” She said, still eyeballing me.
If my mom noticed the way Linda was looking at me, she didn’t let on.
Soon, I left, leaving them to whatever they talk about over coffee.
The following weekend, mom surprised me by asking me to run some stuff over to Linda’s house. I said okay. It took me a few tries to find her place (mom’s directions are never that great), but when I knocked on the door and rang the bell, no one answered. I peered in through a front window. I’m puzzled—I thought I could see a light on inside the house and the patio door out back standing open. Well maybe they have a pool or something out back, so I walked around the house with the bag of stuff and peeked over the pool fence. Oh my God! Linda was lying on a lounge chair in a tiny blue bikini. She looked even better to me now than the other day. I first thought she was sleeping, until she suddenly reached behind her and untied her top. She tossed it aside and then lifted her legs and slid out of her bottoms. She’s completely naked! I can’t move, mesmerized by the sight of a real naked woman right in front of me. She leaned over to a small table next to her and picked up a bottle of lotion, pouring some into the palm of her hand and rubbing it all over herself. When she lifted one leg to coat it with lotion, I saw her pussy…man…all shaved and glistening in the sun! I get an instant woody.
She continued to rub the lotion on, and I continued to watch. If I could jerk off right there, I would have…my hard-on was straining my shorts. Her lotion-slippery hand found its way to her pussy and she began to rub in earnest. She was breathing in short gasps and her nipples were hard and erect like little peckers. What an amazing sight! She’s jerking off…well…I know it’s not right to refer to a woman getting herself off as ‘jerking off’ but damn if that wasn’t what it looked like to me. She stroked her pussy faster and faster, making little moaning sounds, until she must have cum, sorta lifting her pelvis in the air and letting out a low wail.
After she stopped moving and making noises, she turned her head a little to the side and looked like she’d go to sleep. What the hell am I going to do now? I figured I still had to deliver the stuff from my mom, so I started making exaggerated noises by the fence gate hoping she’d hear me and cover up.
“Mrs. Fowler…are you back here?” I called out.
“Who’s there? Is that you, Tom?” She answered.
I opened the gate, saying, “No Mrs. Fowler, it’s Richard…Richard Strong.” As I entered I add “My mom sent me over with some stuff for you.” Like I’m offering proof, I held up the bag in front of me.
Thankfully she threw on a silk robe (though I’m still a little uncomfortable, knowing she’s naked underneath). “Thank you very much, Richard…you’re a dear,” she said, walking toward me. When she was close enough to take the bag from my hand, she crooned, “Your mom’s lucky to have a nice son like you,” while touching my arm. I nearly fainted.
She surprised me even more when she asked, “Why don’t you stay a while and use my pool?”
“But, Mrs. Fowler, I don’t have a suit,” I answered lamely, knowing what she’d say…dreading, yet at the same time thrilled by the idea.
She didn’t disappoint me. “Oh dear boy, you don’t need a suit around here,” she said with a laugh and a small wave of her hand. “No one can see you, and I won’t look at all.” The last said with a big smile on her face. She continued, “besides, I remember how natural and fun it was to skinny-dip when I was your age.”
And I remembered what you’re NOT wearing under that robe.
The alien that’s taking over my brain said, “That’s not a bad idea, I guess…it sure is hot and you’ve got a nice pool, Mrs. Fowler.”
“Oh, phooey, call me Linda…okay Richard?”
She walked toward her lounge chair, picked up the discarded bikini and went into the house. I knew she wouldn’t leave me alone for long; she’d want to check me out, so what the hell, off came my clothes. Her staring eyes be damned; naked, I dove into her pool, enjoying the cool yet not cold water. When I surfaced, I was surprised to see her back near the pool, still wearing the silk robe. Did she put something on underneath? Shit, my cock was getting stiff remembering what she did earlier—I didn’t want to get out of the pool with an erection. I swam around a little more…thinking of anything but her until my ‘buddy’ went down a bit…then climbed up the pool ladder. Of course she’s standing there at the ready with a big beach towel, ogling my cock.
“Well, Richard,” She said, sidling closer but not close enough for me to reach the offered towel. “You are quite a big boy aren’t you?” She dwelled ever so noticeably on the word ‘big.’
While staring at my dick, she ran her tongue along her upper lip then gazed up into my eyes. Oh, man, that look melted me! She finally got close enough to hand me the towel, which I quickly used to cover up, never mind the drying part.
“Now didn’t that dip feel good?” Before I could answer, she asked, “How about a beer? You do drink beer don’t you? …And I don’t want to hear about your age either…I won’t tell your mom.” The last said with her right hand on her chest as if making a pledge. I was still too shell-shocked to answer but managed a nod of my head.
“Great! Why don’t you sit there and keep me company,” she said, pointing to a lounge chair opposite of the one she was in before. “I’ll be right back.”
I had a few ideas of where this was going as I wrapped the towel around my midsection and fell into the chair. I’ve felt up a couple of girls so far, though never to the point where sex was a real possibility. However, Mrs. Fowler—Linda—sure was acting like she wanted ‘something’ from me. My cock stirred under the towel. She came out of the house with a small bucket full of beer bottles on ice, handed me an opened one, took one herself, and relaxed back into her chair. After taking a long swig, she started asking me about school, girlfriends and what sports I liked. As we were talking, she began to hike her knees up a little until I saw a hint of her pussy under the hem of her robe. As I drank my beer, my towel tented upwards and she noticed.
“Boy, this hits the spot,” she said, first lifting her half-empty bottle up then placing it on her chest just above the robe’s edge. “So cool on such a hot day,” she smiled, tilting the bottle up to her lips and draining it. “Ah, that was good…I’m going in for a dip…you coming?”
She accentuated the last word with another lick of her lips. She arose from her lounge chair and dropped the robe. Oh my God, she was standing a few feet from me, naked, and eying the quickly rising area of my towel.
“Come on…don’t be shy,” she said as she trotted over to the pool and dove in.
Up to now, I wasn’t sure of what was going to happen. Now I knew—I was going to lose my virginity today. At the thought, my cock was at full attention, as hard as a rock. Well, there’s no turning back now, I thought, so I got off the chair, tossed the towel aside and dove into the pool. Before I hit the water I saw the look on her face—her eyes seemed, I don’t know, really excited. She swam over to me.
“Nice and cool isn’t it?” When I nod, she added, “Or are you still hot?”
At the same time she was running a hand from my balls up the shaft of my cock. She waded closer and rubbed her tits against my chest, whispering in my ear, “You ever had sex, Richard?” I can hardly breathe—she knew the answer even if I didn’t give her one. “I bet some girl’s told you that you have a fantastic cock.”
She’d be surprised if she knew the only ‘girl’ was my mother.
“You’re no good to me this way,” she said, pulling me toward the pool ladder. What did she mean by that? She scooted me up the ladder and had me sit down on the top rung. Without hesitation she took my cock in her mouth and started sucking me off. I came in about two seconds.
She smiled up at me from the water, cum dribbling from her lips, and said, “See, you wouldn’t have lasted too long…and I need this big guy to perform!”
She pulled me back into the water then stepped up the ladder and out of the pool. Wow, she just gave me my first blowjob, and I couldn’t take my eyes off her round ass, swaying as she walked away. My cock was getting hard again.
As I climbed from the pool she was standing near a lounge chair close to the house, toweling off. I walked toward her, and she dropped the towel and smiled when she saw my erect cock.
“Come here, big boy, and put that fine piece of manhood to good use,” she said, extending her arms out to me.
When I reached her she locked me in an embrace and kissed me as she pulled me on top of her and into the nearest lounge chair. Without any hesitation she lifted and spread her legs widely, guiding my cock into her. The feeling was nothing like I had ever imagined it would be. I breathlessly slid into her wet, warm canal.
“Yes, baby…yes,” she groaned. She started kicking my ass with her heels. “Pump it, baby…oooh, YES…fuck me…fuck me HARD,” she moaned as I started moving into her.
It felt so great! Within seconds I was thrusting my hips and feverishly plunging in and out of her. She moaned and whimpered “Yes” over and over again as my pace uncontrollably quickened.
She screamed through gritted teeth, “Fuck me…Yesssss…you’re filling me…deeper…harder…YES…Aaaaaaaaaaaah,” until she must have cum, which is what I did, thrusting deep into her and spewing several shots, both of us making groaning noises as our bodies continued to grind together. I never felt so good in all my life.
We lay there together until she laughed and said, “For a virgin you sure are a super fuck, you know that, Richard?” I don’t know how to respond to that compliment. After a few minutes she got up and yanked me up with her and led me to the pool. After the hot sex, the cool water felt very good.
Out of the pool and drying off once again, Linda said to me, “I’ve got to kick Tom out of my bed for good this time.”
“Tom?” I asked.
“Yeah, he’s my soon-to-be-ex-boyfriend and sometimes housemate. Don’t worry about him, he’s history.” She reached over and caressed my ass before reaching around in front and palming my cock. “I think I have a new man to share my bed.” My cock stiffened up from her touch—and words. “I’ve found someone who can take care of my needs rather nicely.”
As a horny teenager who just lost his virginity, I was ecstatic. Linda just invited me to be her steady fuck. My cock sprung the rest of the way to full erection.
“Ooh! This is too good to be true,” she said. Taking me by the hand once more, this time she led me into the house and to her bedroom.
The room wasn’t quite as frilly as I expected it to be. The bed, though, was king-size and I instinctively knew we’d use its entire surface.
She climbed onto the bed on her hands and knees and, extending her ass toward me, cooed, “C’mon, Richard, get that beautiful cock into me right now.”
I knew practically nothing about different positions, but I have heard of people doing it ‘doggie-style.’ I guess this was what she wanted. On my knees behind her, I gazed at her glistening wet pussy for a second and saw her pussy lips sort of twitch in anticipation of me. I couldn’t believe my erection could get any bigger, but damn if the sight of her begging womanhood didn’t almost make me cum without even going in.
“C’mon,” she pleaded again. “I need you.” I slid into her slowly, evidently too slow for her, for she barked out, “FUCK ME...GET GOING...NOW!” After I pumped my hips a couple of time, she purred, “That’s it...fuck me with your big cock...Yes...Yes...Uhhhhh...”
I was in heaven. My hips had a mind of their own, maniacally thrusting faster and deeper until a tremendous spasm enveloped my groin and I came. Her moans turned to cries when I ejaculated; the spasms of my cock and probably the warmth of my filling cum must have sent her over the orgasmic precipice. She was louder than before; I was glad she hadn’t screamed like that out by the pool.
We took a shower together before I realized how late it was getting and told her I had to go home. While getting dressed, she giggled and asked me what kind of excuse I could give my mom for coming over again tomorrow. I said I didn’t need an excuse as long as she didn’t find out I was over here. Today I’ve gone from virgin to teenaged gigolo in only a few hours.
The next day was a Sunday. After church I told my mom I was going over a friend’s house when of course I went instead to Linda’s. I think I slept all night with a hard-on, so I was super horny when I slipped between her thighs on that big bed. We were like animals. I was beginning to understand the difference already between ‘fucking’ and ‘making love’—this was fucking.
All the while I was pumping into her, she screamed “Oh God...Yes...hard...HARDER...” over and over again. Boy, did that get me off!
She coaxed my cock back to hardness with her lips and her hands and we fucked again, this time a little slower than before. She cooed and moaned and then screamed. I was so amazed that I was making her feel that good. Was I that good (or my cock that good) or was it her? After our second go-round, we walked naked outside and dove into the pool. I’m not sure if it was even a distant second, but alongside having a willing and experienced fuck-mate, having a nice pool to use any time I wanted was a really nice amenity.
I hated like hell to lie to my mother, but I’d hate it more if she found out about me and Linda. But lie I did, and so two days later I was at Linda’s and we fucked again. She certainly liked it doggie-style; her cums were louder—and wetter—that way. I still didn’t know much about pleasing a woman sexually, but I was learning fast from my new teacher. She liked to experiment, I guess you’d call it, with different positions and angles. One thing remained constant though. She wanted my cock in her pussy. She needed filling.
We did it again on Thursday night when I was supposed to be out with friends. She wasn’t getting tired of fucking me, and I most certainly wasn’t getting tired of her either.
Early the following Saturday, like a puppy that needed to be fed I was over Linda’s in a flash, but she wasn’t home. Since I now had my own key, I let myself in and got naked and jumped into her pool. I swam around and around luxuriating in the cool water until I heard a noise and lifted my head higher to look. Oh my God, there was a naked girl standing on the pool ladder! When she saw me she smiled wryly and stopped, only her feet below the water line.
“You must be my mother’s new fuck,” she said. “Yeah, she told me all about you, except how young you were.”
I saw how she strained to see the parts of my body that were underwater. She was around my age, with a pretty face but a bit on the pudgy side; her thighs especially meaty—ones my mom would call “thunder thighs.” The blonde hair was obviously dyed since I easily saw the contrast with her trimmed yet dark pubic thatch. Her breasts were about average, I guess, though her areolas and nipples were very small, much smaller than her mother’s.
“Wow, I didn’t know Linda had any kids,” was all I could say.
“Well, she, like had me when she was a teenager...you know how those things go. My name’s Sue, by the way.” She continued her descent into the pool as she added, “How old are you anyway? Do you live around here?”
As her feet touched bottom, I hopped up and sat on the pool lip, my feet still dangling in the water. I frankly didn’t know what else to do. Being here naked with her made me nervous as hell. What if Linda came home now?
“Okay, I’m Richard...I’m 15...I live a few blocks down, on Hemlock...need to know anything else?”
She wasn’t listening, her focus on one thing and one thing only.
“Oh...My...God! She said you were hung but I thought she was exaggerating.” She started wading over to me like a moth drawn to light.
I couldn’t help it. As she got closer, my cock twitched a couple of times and started to stiffen. With every twitch her eyes got wider.
“Oh...My...God,” she repeated. By the time she reached me, her eyes had this glazed-over look—one I was beginning to recognize all too well.
Her hand snaked around the shaft of my cock and she started to caress it. There wasn’t much I could do about it, so I just sat there as I grew fully erect. She actually made a small purring noise as she watched my erection grow high and solid.
“Please don’t,” was all I could mutter.
“Oh yes, I definitely need this,” she said, as she suddenly pulled me down into the water. Her lips hungrily met mine, her tongue darting between them and deep into my mouth.
By the time she led me into the house, I was putty to be molded to her wishes. Why did I have that déjà vu feeling when she climbed up on her mother’s bed, oblivious to her still dripping-wet condition, and offered her ass to me? As I said before, her ass was wide, but her pussy still looked inviting, splayed open and wet. I placed the head of my cock at her opening and pushed into her.
She groaned, “You’re stretching me...Yes...all the way...Yes...fill me up...”
I did.
Before I even had a chance to develop a decent rhythm though, she looked back at me and sighed, “You’re doing a great job...your cock feels so good...but I need it in my ass. Fuck me in the ass...NOW,” she begged.
In her ass? This failed to register as a sex act with me (like what the fuck did I know) so I stopped my thrusting and stared at her.
“Damn, you don’t have any idea, do you? Okay,” she said as she rolled over and got a tube of stuff from the nightstand drawer. Opening the tube, she squirted a dollop of the gel into the palm of one hand and then said, “Here, let me show you,” as she spread the jelly-like stuff on the shaft of my cock, making sure most of it was on my swollen cock-head.
Now that I was sufficiently lubricated, she pushed me onto my back and started her spiel. “You’re gonna like this a lot...I’ve been fucked by a lot of guys and I know I’m not that tight...my asshole is a different story...real tight...” She straddled me, facing my feet, and holding my cock in one hand, pushed the head into her anus. “Oh...Oh...Yes...I need this,” she cried as she slowly lowered herself onto me, taking my full length into her ass. “...Yes...you’re so big...oh, yes!”
She leaned back a little and started to fuck me. She was right. Her sphincter was indeed tight, squeezing the shaft of my cock as she bounced up and down on me. Before I even knew it, my orgasm hit; I spewed shot after shot of cum into her rectum. I came so much I could actually feel the warmth of it enveloping my cock as she continued to hump away. The intensity, the tightness, the warmth kept my cock hard enough so she was able to get off. Her groans turned to mewling cries until she fell back upon my chest, put a hand at her pussy and screamed “God, I’m cumming!” She kept writhing on me as she continued to ride the waves of her orgasm.
Laying together on her mother’s bed in post-coital harmony, she told me just about her entire life’s history. She was also 15, but whereas I had recently lost my virginity, she on the other hand was an old pro at sex, having been “fucked by dozens” of men, including her mother’s boyfriend, Tom. I was blown away by her stories of promiscuity. She matter-of-factly told of many of the men and boys she had bedded. To her I was a trophy, one happily stolen from her mother. I wondered if this was a standard game between them.
I was more worried about Linda coming home than Sue was. I managed to talk her into getting dressed and help straighten out the bed; and it was in the nick of time as just then Linda’s car pulled up in the driveway.
“So, you two have met” was Linda’s cool response to seeing us together in her living room.
Maybe I imagined it, but I swear she could see that Sue and I had fucked. Her look was cold and calculating. I guess it was a game between them. Linda kept making comments to her daughter about things she should be doing. Eventually, whether getting the hint or just tired of her mom’s harping I’m not sure, Sue left, leaving us alone.
“How about we get comfortable...relax a bit...?” She asked.
Our clothes were off in record time and we never made the bedroom. She fell back atop the dining room table and I took her right there. While I entered her and began thrusting my hips, she sniffed the air a couple of times. What caught her attention?
I got my answer when she said, “You like ass, huh?” She reached between her splayed legs and grasped my slippery cock, pulling it from her vagina and in one motion slid the head into her anus.
I didn’t know how she knew, but what the fuck—two asses in one morning! I did her hard, and she relished it.
She kept muttering, “Oh, you’re so big...fuck me...fill my ass...you’re so fuckin’ BIG...fuck me...fuck me HARD...” until she came with a wail.
Her spasms set me off as I filled her pulsating bowels with warm semen.
The hot sex was followed by the cold shoulder. Suspecting that I fucked her daughter didn’t stop Linda from wanting some for herself, but otherwise her attitude toward me had changed. I went home soon after our coupling had concluded. But, hey, I’m a horny guy, and now that I’ve tasted the joys of pussy I couldn’t stay away for very long. She wouldn’t call, I knew, but by the following Saturday I needed some loving, so I went over to her house to get some.
Good, her car is in the yard. I thought of this as my second home so I no longer knocked but just walked in. Opening the back door, I called out her name in a low voice. She didn’t answer, so I moved toward the only noise I heard, coming from her bedroom. I was about to say something when I realized what I was hearing. The sing-song of Linda’s ecstatic moans was commingled with the grunts of a male voice. I peeked around the jamb of the open bedroom door to see the unknown man pounding away between her raised and spread legs. This must be Tom, I surmised. I guess I lost my pussy.
I turned to slink away, but something drew me back to watch them fuck. I’m still amazed at what I’ve learned in the last few weeks about sex. My adolescent raging hormones used to create many imaginative fantasies, but now I’ve experienced it for real, thanks to Linda. Even anal sex which I never even thought of, never mind thinking it would be something a girl would enjoy. I was hurt and jealous looking at the two of them fucking, oblivious to my presence. I guess my stupid adolescent mind thought she really cared for me somehow. I took this ‘lover’ thing to heart when all she really wanted was my cock as a plaything. Granted, I didn’t mind being a plaything to her, but somehow wanted this to be more than that.
As I began to turn to leave, I heard him make one final slapping thrust, gruntingly proclaiming, “So...you...want...another...kid, well...here...comes...daddy’s...sperm,” before he groans “Ughhhhh” as he cums.
Another kid? She’s not taking the pill or anything? Don’t you think the ramification of THAT wasn’t lost on me? I slipped out the back door, hoping they hadn’t heard or seen me.
I’m sure you figured out I never got to fuck Linda again. I tried to get in touch with Sue, but she didn’t want to have anything to do with me; so much for her “Oh, my God” reaction to my cock. Several months later I met a nice girl at school and after a few dates we had sex. She wasn’t as experienced as Linda and her daughter, but it was really good anyway. The aftermath of that coupling is what got me into trouble. She must have told the whole female population at my school about my size. Before long, every girl—all the promiscuous ones, at least—wanted a piece of me, and you know what piece they wanted. Needless to say I got lots of action. I always had a condom with me wherever I went. After what I overheard at Linda’s on that fateful day, I figured I was protecting me as much as the girls by using one.
I was surprised the day that my mom told me of Linda’s pregnancy. Linda was coming over, and my mom casually mentioned her condition. When Linda arrived at our door, I was floored by how big she was, her slim curves replaced by one big one. I hung around for a while, a little nervous of what Linda might tell my mom.
She caught me alone when my mom went to get something. “I wonder what this little bundle’s gonna look like?” She said, smiling as she tousled my hair with one hand as she patted her stomach with the other. “It’s a boy you know, and I bet he’ll be a spittin’ image of my Richard.” She leaned in and gave me a kiss on the cheek.
I was so petrified I couldn’t say a word.
She read my expression well. “Oh don’t worry, silly, whatever he looks like it’ll be our secret no matter what. Do you think I want to get in trouble for doing a teenage boy?”
I would never have imagined what came next. She looked around quickly to be sure my mom wasn’t walking into the room and then she rubbed her pregnant belly up against me as she placed a hand on the front of my jeans.
“Did you ever want to fuck a pregnant woman, Richard?” She whispered. “Did you ever wonder what it would feel like, sliding in knowing there’s a baby inside?”
My swelling cock gave her the answer.
Remember I said there would be no more sex with Linda? How could I predict this would happen? Later that afternoon, I was in her bed and rubbing her impressive baby bulge before I slid my hand down to her wet and swollen pussy.
“Oh God Richard, I missed you so much,” she proclaimed, before instructing me to lay in the opposite direction from her. “Eat me, taste me...it’s been so long...”
She struggled onto her side before taking my cock down her throat. My tongue probed and licked, as I realized her taste had changed since being pregnant. I sank my tongue as deep as I could into her as she moaned her approval.
She must have known I was getting ready to cum for she pulled me from her mouth and said, “Quick, spin around and fuck me!”
On my side behind her, I slid in part ways, but hesitated, saying, “Can I, like, hurt the baby if I go all the way?”
She looked back at me over her shoulder, smiled and said, “Well, if you’re so worried, why don’t you put it somewhere else?”
I needed no further explanation as I guided the head of my cock to her anus and pushed into her. Having been in her wet pussy for a moment my cock-head was somewhat lubricated, so I began thrusting almost immediately. I tweaked her clit as I fucked her ass, and she came very quickly. An immense shiver spread through her body as she moaned in orgasm. That was it—I filled her pulsing bowels with cum once again.
She had both her hands on her belly as if trying to quell the climactic tremors that shook her. “Oh...oh...that was SO gooooooood,” she groaned, as I felt another orgasmic wave spread through her. “Shit, I feel like I’m gonna bust and have the kid right now,” she cried.
Did that scare me, or what?
No, those contractions from her orgasm didn’t induce labor, though she said it felt like that to her.
I got dressed and went home, never to sleep with Linda again. As far as I knew my mom never found out. Linda’s kid did look a little like my baby pictures. She showed me a picture of little Ricky naked on a blanket after getting a bath. His cock was already at least two to three inches long, and he was still a baby! He was going to be quite the hung dude, I thought.
Just like me.