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All characters in this story are at least 18 years old when mentioned in a sexual context.
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Since my husband left me for a 22 year old floozy, I dedicated my life to raising my only child, Sam. I was very proud of his good manners and being successful in school. Unfortunately, he was never very social. In fact, he only befriended Tony, who was rather shy as well. I liked Tony; he was very polite, smiled a lot, and whenever I entered Sam's room to serve snacks or soda, his eyes looked at me admiringly.
When Tony turned 18, I consulted my son about a nice present for him. Sam suggested one of the newest video games on the market. I bought it, and also baked a chocolate cake I knew Tony liked. A couple of days later, when Tony visited our home, he thanked me for the expensive game and asked, "Did you bake the cake yourself?"
I smiled, "But of course."
He blushed and mumbled, "The video game was a perfect gift, but I appreciated the cake much more..."
I gazed at him, "I don't believe it, but that was a nice thing to say." He didn't react.
...
Three months later, Sam also turned 18. He chose to celebrate it in his room with Tony as his only guest. He begged me to let them have beer. I wasn't sure if it was legal at his age, but gave up: It was his birthday, and what could go wrong if the two of them stayed in Sam's room?
I dressed nicely for the occasion, hoping to make my growing son happy. When Tony arrived, I noticed his eyes wandering over my short dress before he joined Sam in his room. They played games, and once in a while, I entered, bringing pizza, snacks, or ice cream. In the first hour, the room was relatively quiet, except for happy loud voices when one of the boys won.
Later, I was on my way to bring cold soda, when I heard Sam shout, "Go to hell!"
I stopped in my tracks by the door and listened, but Tony's voice was too low, and I was not able to decipher his words. Sam growled, "Tony, you are sick. I want you to leave now!"
I was about to open the door and see what the ruckus was all about when I heard a knock and then somebody landing on the floor. I entered and noticed Tony on his back on the rug with a reddish mark on his forehead.
I stood between them and turned to Sam, "Honey, what's going on? You are buddies, and Tony is your guest. What is wrong?"
Sam had tears in his eyes, "I want Tony to leave. NOW! He is a jerk."
"Sammy, why?"
"He is a pervert, and I don't want to see him. EVER!"
I glanced at Tony, whose face was beet-red. Since it was Sam's birthday, and he was reluctant to elaborate on his claim, I just stared at the guys, watched Tony slowly rise from the floor, and leave.
When Tony was gone, I sat on Sam's bed's edge and asked, "Please, tell me what was so upsetting."
Sam looked at me and said, "He offended you."
I was puzzled, "I thought he liked me..."
"The idiot called you a MILF!"
"What?!..."
"After drinking the beer and finishing several games, we talked about girls. He said he watched me eyeing Barbara in school. I admitted I liked her and asked him who was HIS favorite girl. He said that all our classmates were too childish, and he was more into more mature females. I assumed he meant girls who were 2-3 years older and wanted to know more details. He didn't hesitate and said, 'Your mother. She is a real MILF.' You see what I mean? This imbecile dares to fantasize about you! He crossed the line, and I no longer want him here."
Sam finished, and the veins in his neck bulged, threatening to explode. It was clear there was no way I could calm him now, so I said, "I understand. Let's go to sleep and talk it over later."
...
While in bed, I began thinking: I haven't heard the term MILF in a long time. While it sounded offensive, the previous time I heard it was from my prior husband, describing our young neighbor appreciatively. Did Tony really have fantasies about me? I knew I looked good for my age: At 41, I was 5'4", 132 pounds, dirty blonde, wavy hair, hazel eyes, and was told by my girlfriends I was too cute to be without a man for the rest of my life. My curvy figure attracted the attention of men, but after my husband's betrayal, for years I was too insecure and refused to meet another guy.
Tony's admission made me think about my situation: I was now a decent-looking middle aged woman with a growing son who was about to go to college next year, so I'd be all alone. I had a few good girlfriends that I met on a regular basis, but much of the time I was listening to their adventures with men. One of them, Livia, was married, but loved to brag about her full-of-stamina, young lover. Her detailed description of their bedtime reminded me of my happy years, when I was younger, and sex with my husband was very satisfying. Nowadays, my Jack Rabbit was doing a much less pleasant job...
My thoughts turned to Tony. As I mentioned, he was very shy, but he looked attractive: About 6', 180 pounds, dark brown skin, and good muscle tone. He must still be a virgin. I recalled seeing him and Sam playing in our pool and thinking he was a hunk.
Now, realizing Tony's mind was concentrating on me as a sexy woman, a feeling of warmth enveloped my body. All of a sudden, I found my fingers lightly tweaking my breast, and my vulva started leaking. I tried to tell myself Tony's words meant nothing: at the time he must have been drunk, but to no avail. The prolonged drought flooded my brain with erotic thoughts.
I convinced myself that, as a good mother, it was my duty to reconnect my son with Tony. I had to phone Tony, meet with him, and persuade him to continue their friendship. Just before I fell asleep, a little voice in my mind whispered, 'Lady, are you sure that your intention is pure?...'
...
The following day I went as usual to exercise at the health center with my brain occupied by a single thought: how should I talk to Tony? Eventually, I chose the simplest way; invite him to the local coffee shop and explain to him that the way he addressed me when talking to my son crossed a red line.
In the afternoon, once Sam left the house for an errand, I phoned Tony. He responded immediately, but initially didn't recognize me.
I said, "Tony, this is Sam's mother, Linda."
He stuttered, "Ma'am, I aam really sorry for my iinexcusable behavior at Saam's birthday."
I smiled, "Tony, I have no doubt you did not intend to offend me, but MILF is a bad word. Anyway, I do not think that Sam and you should stop being friends over a silly reason like that. Let's meet at the nearest Starbucks and talk it over."
"Aare you going to chastise mee for being stupid?..."
I laughed, "Not really, but I'd like to clarify why you said it. Can you come to Starbucks at 8 pm tonight?"
He hesitated and then sighed, "OK, ma'am. I'll be there."
After dinner with Sam, he went to his room and closed the door behind him, probably to work on his computer.
I showered and thought about how to dress. I knew that the appropriate way was to dress conservatively, but the naughty part of my brain whispered that it would be fun to see Tony's reaction if I dressed more riske. I put on a beige, short dress that emphasized my ample chest and shapely legs, added a matching 3" heel shoes, and glossy red lipstick. I grinned, watching myself in the mirror, recalling that the last time I dressed like that was years ago. I knocked on Sam's door, and without opening it, I said, "I'm leaving to visit Debra."
He answered, "See you later."
...
When I arrived, Tony was already sitting at a table for two. He wore khakis and a clean light blue shirt. As he saw me, his mouth opened, and his eyes explored me up and down, with his face flushed. I smiled at him, feeling young and happy, "Did you wait long for me?"
"I arrived 15 minutes ago to make sure we had a table to sit at." He stood up, "What can I bring you?"
"A small latte, please."
He moved away, and I inspected his rear. Tony was built well, and I thought that there was nothing physically wrong with him. If not for his shyness, girls would have gone gaga over him. Could it be that he wasn't so shy, but was really so attracted to me that his demure behavior only came out in my presence?!...
Tony returned to our table with my latte and his black coffee. He looked nervous and eyed me, waiting for the verdict.
I smiled at him, "Tony, relax, I already forgave you. Tell me, is it true that you find me attractive or it was just a silly talk while you were drunk?"
He lowered his eyes and mumbled, "I think you are the best looking woman I've ever seen..."
"Why? I've seen a couple of girls from your class, and they are younger, prettier, and in my opinion, will be much more interesting than a middle aged woman like me."
He gazed at me pleadingly, "I don't think so. I think you look terrific..."
While deep down I felt fantastic, I sighed dramatically, and blurted, "Tony, it's too crowded and noisy here. This is not the place to have a serious talk. Tell you what; Saturday late morning Sam will visit his cousin, and I'll be free. Can you come to my house at 10 am?"
Tony muttered, "OK..."
For the next half an hour, I interrogated him about school stuff, and then I left, reminding him again to show up on Saturday morning.
...
On Saturday, I waited impatiently for Sam to leave before rearranging the living room and kitchen to look better, and later made sure my bedroom looked and smelled perfect. I took a long bath, then wore my favorite long, thin robe, which was tied by a cloth belt at the waist, applied a thin layer of makeup and red hot lipstick, and sat down.
Tony knocked softly on the door 5 minutes early. I opened the door. Tony's eyes ogled my figure while handing me a bouquet of pink roses and mumbling, "This is as a token for my unforgivable talk with Sam."
I sniffed the smelly flowers and grinned, "Thank you. They are beautiful. Sit down on the sofa while I put these in a proper vase. What would you drink? Coffee? Tea? Cola?"
I noticed his eyes still wandered my hardly covered body, pausing on my protruding chest. He said, "Cola will be fine."
As I was walking toward the kitchen, I felt his eyes burning my backside, and my walk turned into sashay. My brain protested, 'Lady, what the hell are you doing?'
I ignored it, feeling young and energized again. I placed my tea on a tray, poured cola into a glass for Tony, and returned to the living room. His eyes never left me.
I smiled, bent down to serve him with the cola, and heard him gasp. I knew immediately what the reason was: as I leaned forward, my robe separated from my body, and much of my large breasts got exposed to his wandering eyes. An electric shock went through my body, and I felt I was getting aroused. My face flushed, and my knees grew weak. I sat down on his side and gazed at Tony's face. For a while, his mouth was agape, and then he mumbled, "You are so gorgeous..."
After what felt like an hour, I found my voice, "Tony, instead of looking at my face, your eyes are directed at my body, mostly at my chest. What is it? Haven't you seen women with large boobs before?"
He crossed his legs and lowered his gaze. I stared at his groin. A huge bulge was noted in his front. After watching my tits, this young fellow had a massive erection! I was already primed and felt my coochie getting wet.
I moved closer to Tony and murmured, "Tell me the truth; have you ever had sex with a girl?"
He whispered, "I had, once, but it was in the dark, in my car, and it lasted only a couple of minutes..."
"So you haven't seen her breasts?"
"No..."
"I see you are obsessed with mine. Will you feel better if you see them?"
He looked at me, not believing his ears, "Whaat?..."
I stared at his still growing tent, "You seem to be uncomfortable. Will the sight of my bare tits help?"
He never said a word, but his begging eyes were sufficient to assure me he'd be willing to kill to see them.
I lowered the top of my robe at a snail's pace, letting it fall to my waist. I pushed my chest forward, and my stiff nipples moved upward, facing him.
He swallowed his saliva, and the front of his pants stretched ominously. His eyes focused on my round mammaries, and his lips got dry. He looked aroused beyond belief, and so was I.
After a short pause, I heard myself asking him in a husky voice, "Would you like to touch them?"
His eyes widened, and he glanced at me speechless.
I took his palm, placed it on my left breast, and whispered, "Feel my pulse. My heart rate is more than 100. I am as excited as you."
Tony's eyes shifted back to my tits, and slowly his fingers began kneading my firm breast. My horniness was over the roof, and next, my fingers moved to fondle his covered organ. He moaned, and his fingers massaged my tit faster. I leaned backward, closed my eyes, and my hand started unzipping his fly.
His legs parted, and his pelvis rose to facilitate my ministrations. When the zipper was lowered enough, his rigid member jolted forward, hitting my palm. I opened my eyes and saw the tip of a raging cock peeking above the waist of his briefs. The helmet was purple, large, and had a noticeable eye. I lowered the briefs further, exposing the thick shaft. It felt velvety with bulging veins, and the base was covered with black hair.
Tony's magnificent pole was very tempting. I lasted only a few seconds before bending down and engulfing it with my lips. He groaned, and his palms moved to the sides of my head. I began bobbing the monster, feeling it swell and harden further in my mouth. In less than a minute, his body tensed, and a stream of slimy fluid filled my oral cavity. I swallowed as fast as I could, spilling only a couple of drops on his lap.
When he was done, he let go. I raised my head and looked him in the eye. He mumbled, "Sorry, Linda. You are so sexy, and what you were doing was so enjoyable that I couldn't stop..."
I smiled, "I knew what would happen the moment I started sucking you. No apologies needed because I loved giving you head. However, I didn't come, and I am still horny. Can you help?..."
His eyes pierced mine, "Do you mean a hand job? oral? or... something else?"
I grinned, "You just emptied yourself. When will you be able to perform the 'something else'?"
He chuckled and put my tiny palm on his reemerging erection, "Lady, your body is so hot, that I'll be ready very soon."
I whispered, "Let's go to my bedroom."
He followed me like a hungry puppy. I unclasped the belt, and it landed on the soft rug. I lay supine on the bed, spread my thighs, and glanced at Tony. His eyes explored my body slowly, as his phallus grew before my eyes. Then he undressed completely, letting my eyes take a good look at his tumescent pecker, and then dove headfirst onto my soaked cunt. It was obvious that he was inexperienced, but at my extremely aroused state, his clumsy trial was enough to send me over the edge. I was shivering, jiggling, and screaming like a wounded animal, unable to stop myself. He continued licking my clitoris and fingering me for a couple of minutes, then moved up, and inserted his cock gingerly into my boiling pussy.
I guess after years of not having sex, my tunnel shrank somewhat because I felt his organ stretching my pussy to the limit. Once he was all inside, I felt him all the way to my throat. Tony started thrusting into me like a runaway train. No gradual acceleration and no finesse: his beast plowed into me like a bull in heat.
In the beginning I was too overwhelmed by his roughness, but shortly after, feeling my arousal mounting again, my body reacted, countering his strokes and falling into the abyss once again. I felt myself being up above and watching us fucking wildly like horny animals. It wasn't making love and not even a sexual act the way I remembered it; it was a brutal act of pull and push, invade and retreat, a relentless act of nonstop drilling my abused yet hungry pussy.
I had no idea how long our encounter lasted, but I was so exhausted that I fell asleep as soon as Tony dumped his load deep in my womb and moved away. I woke up at 12:30 pm. Tony was gone, and there was a note on the bed, "Linda, you were wonderful. Thank you. I'd love to see you again. PLEASE..."
I smiled. I felt lightheaded, and my cunt burnt, but the rest of my body felt invigorated like at my honeymoon, a thousand years ago. The shy youngster turned out to be a god-sent sex partner; he was inexperienced and needed some pointers, but his physique and stamina were awesome!
Sam returned home later that evening. I was very cheerful. He noticed and grinned, "I see your day was pleasant."
"Yes, it was. How was yours?"
Sam began telling me about his visit to his cousin, but I was hardly listening. Tony ravaging of my body was floating before my eyes. After a couple of minutes he noticed I wasn't listening, so he went to his room to watch TV.
The same night, I had a dream: Tony and I were strolling hand in hand in a state park nearby. Out of nowhere, Sam showed up. He looked at me and asked, "Mom, how could you? And with Tony nonetheless?!..."
I blurted, "You know nothing about Tony. He is amazing."
"But he is only 18, and he is my enemy..."
"You two should make peace because I like him."
Sam looked at me with disappointment in his eyes, "Oh Mom, you too?!..." Then he disappeared.
I woke up feeling guilty. It took me almost an hour to fall asleep again.
...
The next day I called Tony. He answered, "Hi Linda. I missed you already."
"Tony, I like you, and I cannot deny that the sex yesterday was fun, but it was also a wake up call. We'll never do it again."
He blurted, "That's out of the question. I think I love you. Before our encounter I was obsessed with you, but having you in my arms, smelling your sweet odor, tasting your nectar, and having a blissful sex with the woman of my dreams convinced me we are destined to continue our relationship."
"Tony dear, you are young and naive. A one time sex, as satisfying as it was, does not always lead to a long term relationship."
"Linda, you said yourself that you enjoyed yesterday's act, so why not continue?"
"Because we might get caught and my relationship with my son destroyed. I love Sam too much to risk it."
"Please, give me a chance to change your mind in person."
The longer our phone conversation continued, the more I felt weaker to explain my point of view. His youngish, stubborn insistence took a toll on me, and I gave up, "Tony, Sam seems to be very grouchy lately. I think it's due to his fight with you and lack of other friends to play with. If you promise to apologize to Sam for calling me a MILF, and say you were drunk at the time, I'll agree to meet with you and listen to your arguments."
"Thank you, ma'am. I'll do my best, and even bow to him if need be, so I'll see you again."
"Tony, let me know if your friendship with Sam resumes. If you are successful, I'll see you the upcoming Saturday." I hung up the phone, feeling good: Sam will have his friend back, and the only thing I promised in return was to listen to Tony talk.
In the afternoon the following day, Sam returned home smiling. I asked him for the reason.
He said, "On a break, Tony came to me half crying and said he felt terrible for offending you. He claimed he was so drunk that he hardly remembered the reason for our fight. He looked so miserable, that I agreed to forgive him if he apologized profusely to you in my presence."
I hugged Sam, "You are a good son. Thank you."
"Tony will be here in an hour to tell you how sorry he is."
"Oh, OK..."
I showered, put on a decent dress, but also added red lipstick and a touch of perfume. Luckily, I still had a couple slices of the chocolate cake and frozen pizza. I was scared to death that Sam would notice the tension in the air, but hoped to pass this unexpected test...
Tony arrived well dressed. In front of Sam, he handed me a dozen white roses, gazed into my eyes as if he had never met me outside our house, and said in a low voice, "Ma'am, in my drunken state, I was the biggest moron and blubbered stupid things. It was inexcusable, and I regret my words. Would you, PLEASE, forgive me?..."
I grinned, "Tony, I always liked you and was amazed hearing the way you talked about me. But I realized you were under the influence at the time, which was partly my fault; after all, I supplied the beer. So I forgive you."
"Thank you, and I vow to NEVER disrespect you again for as long as I live."
I giggled, "That will be nice. Would you like a piece of chocolate cake with soda?"
"Yes. Thank you."
I gave the boys cake and soda, and they entered Sam's room. I breathed a sigh of relief and went to my room. The guys spent 2 hours there, and then I heard Tony leaving. Not five minutes passed, and my phone rang. It was Tony, "Linda, I made peace with your son. What time on Saturday will I see you?"
I laughed, "You played your cards beautifully. Now, Sam is going to be home Saturday morning, so I'll tell him I will be driving to a girlfriend. We can meet at the entrance to the nearby park at 10 am."
"I'll be there. And... I love you!"
I hung up the phone.
...
Three days after the escapade with Tony, my cheerful spirit changed. I wasn't depressed, but something was missing. In addition, I began feeling an emptiness and an itch in my pussy. It was as if my cunt wanted to be filled again, and the initial wonderful mood I felt (afterglow?) disappeared. It was a new and annoying feeling. What the hell?!...
I knew it would be our last private meeting, so I wanted to leave a good impression. I wore a short, tight blue dress that hugged my curves and showed generous cleavage. I put on high heels, left my wavy hair loose, and added a red lipstick.
When I parked my car, I saw Tony standing by his, glancing in my direction. He wore tight jeans and a T shirt which revealed his shapely biceps.
I got out smiling, and joined him. He whistled and said, "Linda, you look stunning!"
"You dressed simply, but you are a real stud yourself."
He winked, "Does it mean I still have a chance?"
"Tony, I explained to you on the phone that it's not that I am not attracted to you, but our relationship has no future. You are in my son's class, and soon you'll find a girl your age."
"I don't want a girl my age. I want you, and ONLY YOU!"
"Please, darling, be realistic. You know I am right."
"Why do you always insert your age into the discussion? The chronological age means nothing to me. The only thing that matters is that neither of us is attached and we both like our intimacy."
Hearing him reminded me of our pleasurable sexual encounter. The itch in my pussy intensified, and my vulva started leaking. I knew I was losing my resolve and tried one last time, "Tony, we cannot continue being intimate. You are Sam's best friend, and we cannot hide our relations forever..."
His eyes inspected mine and felt like a dagger. I looked at the floor, but already knew he was winning the battle.
Next, he took my arm, folded it in his, and we began strolling on the trail. After 50 yards, he pulled me behind a large tree and kissed me passionately. It left me breathless. I could only look at him. His unmistakably hungry eyes told me everything I needed to know. He wanted my body, all of me, and I was about to give in to his demands.
Then he took me in his arms again, French kissed me, and his hand started roaming my chest. I was helpless in his strong hands, mentally unable to object. His hands penetrated the upper part of my dress and cupped my tit. My arousal shot up, and I was like a putty in his hands. He ground a gigantic erection onto my pelvis, making me dizzy with lust.
I could barely talk and mumbled, "Honey, we cannot continue here. Somebody will see us..."
He said, "You are right. Let's go to the nearest Quality Inn."
I didn't argue, and he gently pulled me back to his car. We didn't speak during the 10 minute drive. He registered us, and then we climbed to room 213. As the door closed behind us, he unzipped my dress, let it fall down, released my bra, and latched to my left nipple like a baby. My right hand caressed his hair while my left grabbed his crotch.
Subsequently, he lifted me in his arms, carried me to the king size bed, removed my soaked panties, undressed quickly, and climbed between my knees. He mounted my legs on his shoulders and drove his steely hard cock into my exposed pussy. I was drenched and more than ready for him. His pounding was rapid and powerful, and soon I began trembling erratically. He rammed his monster mercilessly, sending me higher and higher toward status orgasm. I could hear myself in the distance, mumbling, "My god!... So good... I caan't..."
Tony ignored my half sentences and increased his pace until I lost it completely. I had no idea what was going on except that I was in heaven... Every now and then I felt his large palms ravaging my tits and pinching my sensitive nipples, and his giant prick trying to burst my cervix, but I cared less; I was on cloud nine.
After a long time, his body extended, and he crushed mine. Seconds later, he ejaculated into me with loud grunts. Then he rolled onto my side and closed his eyes.
I rested for a couple of minutes and then looked at his chest, still heaving. At that moment, I felt he was my savior. I leaned down on him, licked his stained, shriveling penis, enveloped it with my lips, and rested my head on his groin. I milked the last few drops of semen and continued leisurely sucking the marvelous organ. My intention was to fall asleep with the human pacifier in my mouth, but it was not meant to be; before my eyes closed, his tool started growing and hardening, and Tony blurted, "You played with fire, and now you'll have to suffer the consequences. Would you rather be fucked again or oral?"
I smiled, "You abused my coochie too much for one day. But sucking you will be fun."
I let 6" invade my mouth and wrapped my palm around the base of his cock before beginning to bob it forcefully. He was about to cum after less than 10 minutes, but I constricted the base of his dick, not allowing him to ejaculate. He squirmed but didn't say anything. I slowed my manipulations, and the cock started deflating. I intensified my oral job, squeezing his member between my tongue and my palate while milking it as I was pulling out. His pecker stiffened rapidly again. This time, my other hand jiggled his nuts tenderly. He exploded down my throat with a continuous stream of hot lava. I gulped his whitish goo dutifully.
After cleaning his genitals with my tongue once again, I gazed at him. His eyes expressed admiration, and he blurted, "Linda dear, I'll never let you go. You are too precious."
...
In the days and weeks that followed, Tony and I continued to meet in hotels nearby for gratifying sex. He was obsessed with me, and I became addicted to his sexual prowess. Once he had a cold and we met after 2 weeks of drought. It was torture for me, with constant itch in my cunt and depressed mood, but the return to action was like a honeymoon with a sexual encounter that lasted on and off for hours. I jokingly warned him to never dare get sick again. He kissed my lips tenderly and whispered, "Honey, I suffered even more than you when we were away from each other."
These days, a year and a half after our first intimate moment, Sam and Tony are in college, but they major in different subjects. They are still buddies and see each other no less than once a week. Tony and I continue pretending we were simply his friend and his mother, respectively, showing no signs that we were spending quality time in bed every so often.
Deep down, I know our relationship cannot last much longer, but for now I take the benefits of Tony's sexual stamina and live for today. I never divulged the relationship to anyone, including my gossipy girlfriends, who were more than willing to brag about their love conquests. And luckily, Tony also kept his mouth shut. Even my guilt trip decreased to a bare minimum.
I like Tony a lot, but I do not love him. I believe he feels he is in love with me. As long as our shenanigans are kept secret and both of us have fun, I intend to keep it, feeling more energized than before.
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