My Step-mom has the hottest friends. They get together once a week for "Book club" where they basically sit around drinking wine all afternoon and talk about some stupid romance novel or something. They're all super hot MILFs, and I always seem to find some reason to walk through the living room to get a peek at them. They love to flirt and embarrass me, and it really turns me on when they do. The more wine they drink, the flirtier they get. One of them even kissed me in the kitchen while my mom was reading something from a book with the rest of the ladies. My mom is nothing to sneeze at either. She's actually the hottest one of the group, and I heard them teasing her about me more than once. It seems that they all have young boy toys that they play with, and were making fun of her for not having one. Well, when she called me in to her room to talk, I was shocked when she said that her friends said that I had been flirting with THEM. I thought she was mad at me for embarrassing her, but she told me that she was actually concerned that I was thinking about doing something with one of her friends and that I was fixated on older women. She said that she wanted to be a grand mom one day, and that wouldn't happen if I ended up with a Cougar. She said that she wanted to help me get my curiosity about older women out of my system right then and there. She told me to lay down on her bed. She took off her top and let me see her enormous round tits in her sexy bra. My cock was growing as she unzipped my jeans and began to rub me over my underwear. She breathed on my cock and I could feel her hot breath with only the fabric of my shorts between her mouth and my dick. Mom pulled my cock out of the top of my underwear and put her mouth over it, slurping it deep into her mouth. I couldn't believe my luck, here I was getting sucked off by the hottest MILF on the planet - my mom! She stroked it with two hands, twisting her fingers as she milked it. "You're such a good boy," she said and then plunged her mouth over the head again. She took off her bra and slid my cock between her fleshy mounds. "Your dad likes when I do this to him", she said. "How come you never hit on me?" she asked. "Aren't I cougar enough for you?" I think my mom was actually jealous! She continued to suck and slurp on my rod, alternating with her hands. I felt like I could go any minute. "There are other games we can play too," she said. She knelt up above the head of my stiff dick, and pulled her panties to the side. She had an enormous clit and a bush! She took the head of my cock and ran it along her pussy lips. "How about if we play Hide-the-Tip?" she asked. She slipped the first inch of my cock between her velvety soft pussy lips and into her wet hole. All I had to do was thrust my hips upward and I would be fucking my mom! I didn't have time for that, as she kneeled back between my legs and stroked me faster. "I want to taste your cum" she said. She pumped and pumped and finally I exploded in her hand. Mom licked the cum from her fingers and sucked the last remaining drops from my rod. "Now you stop hitting on my girlfriends," she said as she wagged her finger at me. "If you want a cougar, you come to me, and only me. It'll be our secret".

I thought I had my masturbation/sex addiction under control. I live in the college dorms where there is always someone around, not much privacy for me to indulge in my needs. I few weeks ago I was able to get a girl to my room for some fucking time when I got caught by the RA (Resident Assistant). We aren't supposed to have girls in our room. I figured if we didn't moan too loud then no one would even know we were there. I was wrong. The school immediately called my step-mom to let her know I would be suspended from school if I dis-obeyed the college ordinances again. My mom acted pretty calm over the phone when I spoke with her after the Dean was finished basically telling her what a fuck up I am. I was anticipating her to be completely upset with me but she wasn't. I went home the following weekend and found out why my mom didn't sound so upset with me over the phone. She had something awaiting me as my punishment. She had a very disappointed look in her eyes as she explained I was going to wear a chastity as my punishment for getting caught with a girl in my room at school. I saw these things on the internet but hadn't ever seen one up close. I was hesitant and slightly resistant to the idea of my cock being under my mom's complete control. I knew I had done wrong but to take away my main source of pleasure was just cruel. She knows I have a masturbation addiction. I don't tell her much about all the pussies I've fucked cause I think she would be a little jealous. I don't know if its true but there is a slight weirdness to my relationship with my mom. It's something I feel from her. I feel like she wants to control all of life and she does not seem happy when I talk of girls I am hanging with. I feel I have to kind of do as she says since she is the one doling out the money for my car and school. My dad left us a lot of money but all in her name, so I want to keep her happy. I figure this is just her way of making an impact on me but by next week or so the control she feels will wear off and she will take this thing off my cock and forget about putting it back on. I will have my freedom to fuck when I want even if it is just my own hand. I will do anything to get my dick back where it belongs, free balling in my boxer briefs. Only thing is, when she released my cock from its plastic lock box, she seemed a little too happy to be wearing the key around her neck. My suspicions were right, she does have a weirdness toward me. Truth is, I want this. I do want my mom to have complete control of my cock. I do crave for her to release me week after week. To keep her happy, I will do anything.

My stepmom has no idea how much I think about her. She probably sees me as just another college kid slacker who holes up in his room all day being anti-social. If she only knew what I've imagined her doing to me in my fantasy she would possibly send me to counseling. She's just a regular mom like many other moms out there except she has something special to her. She wears frumpy clothes and eye glasses that fall down her nose but I see something else when I look at her. I see her hair softly curled and hanging loose to frame her beautiful face. I see her in gorgeous vintage lingerie with stockings and elegant elbow length gloves. She would wear sexy black satin wedges with rhinestone bows to match the bows on her lingerie garter strap. Her lips would be crimson red like a perfect red rose, most important, she would be wearing pearls that hung down in between her still scrumptious middle aged breasts. Ahh... I have blasted my hot cum many a time by my own hand to this fantasy of her. If she could only see herself as I do maybe she might dress up a little more instead of looking like she just got out of yoga class. Oh well, maybe it will just have to be my twisted little fantasy that no one else will ever know about, or will they? She is dressed exactly as I imagined. Here she is in my own bedroom! All her attention is directed to me. She moves her perfect body seductively to show every curve accented in her lingerie. After she gives me quite the visual tease she slowly comes to me and goes right for the bulge that is growing by the second. She tells me how long she has wanted a moment like this to happen, us, alone. I lay there as if I am dreaming but don't want to move in case I should wake up and this isn't real. My cock is in her hands, wrapped in her pearls and cradled by her gloved fingertips. She sucks and strokes my hard on so perfectly well. She tells me how much she loves the feel of my dick in her hands. Before I knew it she was straddling me and asking for my load. She said to give my cum to mommy. This drove me to the point of no return as I let every ounce of hot spunk pump from my swollen member. She milked it until it was dry and then licked the last drop from the tip. My step mom tasting my jizz! I must be day dreaming again,...or am I?

How long were you standing outside my bedroom door? I can't believe you were perving on me and my special friend. What you saw us doing can't be repeated especially to your father. I love your father but I have certain needs that he doesn't meet and for this I keep special friends. Since you creeped out my friend who was just here by spying on us, now you get to take his place. You're only my step son so it doesn't matter if I use your cock for my pleasure and play toy. It may seem a little strange to you but then so is spying on your step mother. I would think you would be so busy with college girls that you wouldn't have time to hang around the house as much as you do. Do you have a weird thing for older women? Is that why you were looking at me suck my friends cock?

I was pretty excited to get out of school early today. Some days college requires to much concentration for me. I was looking forward to going home and laying around in my room until dinner. Ahh, lazy days like these are so much appreciated. I had no more than walked in the house when I saw my stepmom down on all fours washing the slate floor. Sure, I fantasize quite a lot about my stepmom. She has a pretty nice body for her age and she is super cool to me. I have to stretch my imagination when I'm rubbing one out to her though because she always dresses so, how do I say…tacky? I mean I know she is at home all day cleaning and other motherly duties around the house but she doesn't know how to co-ordinate her clothes at all. She throws on whatever happens to be within reach. Not that I mind when she wears her old jean mini skirt but if she could only do something with her hair and wear some lipstick it would sure help my cause when I'm alone in my room frantically trying to pop a load without getting caught. When I saw her today in her usual jean skirt and old layered shirts I immediately started transforming her in my mind to the perfectly poised and sexy mom I want her to be for my cock cranking fantasy. She wouldn't make small talk with me, she would arch her back as she is on all fours so her ass is nice and high then invite me to follow her ever so gracefully as she prepares me for a little motherly love on my young manhood. She would be dressed in a hot pink chemise, which showcases her breasts and curve of her hips. She speaks slow and seductively saying how happy she is to have me home early so she can help relive some of my pent up stress from school. She touches me with her perfectly pedicured feet inside her silky pantyhose. I lay back and watch as she slides her hands down her hose, and plays with herself and watched my dick grow as a result of her titillation. I love when she wears stockings because it makes me think of all that goodness wrapped tightly inside. I feel my worries of the day melt away as she strips her stockings off and her panties so she can slide herself onto my knob. Her moist pussy waxes my knob and my shaft as she slides up and down. When my dick is nice and lubed with her pussy juice she uses those mature hands to stroke me off so damn good. She knelt in front of me so I could see her tits and her bush while she milked the cream from cock. She gave me her silky stockings that she thought said Mommy on them but I haven't the heart to tell her otherwise. It doesn't matter, she wiped my cum with them and told me to smell them later when I hear my dad fucking her in the next room to remind me what she will do for me anytime I want. A tender loving mommy hand job.

It's not my intent to embarrass you but we must talk about a very important issue at hand. I've waited until everyone is asleep so don't worry about anyone hearing this conversation. Are you curious why I brought a ten pack of tissue boxes in your bedroom? You should be curious. I present one incredibly stiff and crunchy sock as evidence to support the reason you need a large supply of tissues at all times. I know why this sock is stiff. You're jacking of and leaving your jerk wad in clothing! This is unacceptable! I can't cringe every time I load the washing machine with your clothes anymore. I respect your privacy and the need to unload all that pent up angst from your cock but not in your clothing anymore! Besides being unsanitary and completely gross, it's not a healthy habit for a guy your age to establish. You're college age now and need to learn to at least hide the evidence of your daily activities with your penis a little better. So we are perfectly clear what I expect of you I am going to demonstrate the complete procedure for disposing of your shall we say, waste. Have you not given any thought at all to the fact that when your cum soaked stiff articles of clothing are put in the wash with the rest of the laundry, your DNA is swimming around contaminating our clothes? No more will this happen. I can hardly believe you're actually hard with an erection. Did this conversation and scolding excite you? I will show you how easy it is to grab a few tissues and wipe all your cum load away. I even bought trash liners for your little garbage bin here in your bedroom. You can empty it yourself when it get's full. I don't imagine at your age, a full basket of cum rags with take long to acquire. You probably get hard from a gust of wind blowing your way. I understand the need to stroke your cock and release that pent up pressure. I think giving you these tissues will satisfy both of our needs when it comes to your cum disposal. Speaking of disposal, I want to get back to sleep so go ahead relax and give me that hot load. Go ahead, relax and give me that nice big load you have. I don't mind showing you a little skin to hurry this along. Give my mommie titties a look while I continue to stroke you to ejaculation. I'm ready for it. Oh My Gosh! I had no idea you were capable of THAT much ejaculation! No wonder you use your clothing for your enormous loads. You may run out of this stash of tissues sooner than I expected! Ok, well I need to somehow go down the hall and wash your mess off me and get back to bed before your father wakes up. I don't know many stepmothers who would go through such lengths to educate their son's in this matter.

I have the greatest stepmom ever. Not only is she hot, she's also very cool and not like most women her age. The truth is, I've had the hots for her for years, and have sort of developed a fetish for her panties. I used to steal them from the hamper and jack off while smelling them. I loved the feeling of the soft silky fabric rubbing against my dick, and knowing that my mom's pussy was against the material always made me blow the biggest loads. I always made sure to put the panties back in the hamper though, so she didn't catch on that I was wanking in her worn panties. Until today, that is. My mom called me into her room and had a bunch of her panties laid out on the bed in front of her. I was mortified when she told me that she found a pair of her panties stuffed under my mattress. I took them that morning and figured I'd get a good chance to stroke my cock with them later that night. I didn't expect my mom to change my dirty sheets and find them. She was very cool about it though, and told me that it is perfectly OK. She told me that a lot of guys have a panty fetish and get off to the scent of worn women's underwear. I couldn't believe that she wasn't pissed and threatening to tell my dad! Then she dropped a bombshell. She told me that it turned her on, and that she had a fetish as well... for young cock! She said that she really wanted to feel my cock in her hands, and that this gave her the perfect opportunity to do so. My mom took off her panties and handed them to me, and told me that I could smell them while she jerked me off! She wanted to let me feel all sorts of different panties on my penis, so she took my cock out of my pants and began to stroke me with a soft, silky pair to begin with. They felt amazing! She rubbed them over my cock head, and back down again. Here I was, laying in my parents bed with my step-mom sliding her hand up and down my rod. She kept her panties wrapped around the base and began to really crank my cock. The entire time she stroked me, she kept saying the filthiest things about how I was a little panty boy and that I needed my mom to make me cum. I blew a thick load all over her hand, and she wiped it all up with the silky pink panties. She then gave me the panties to keep, and promised me that we could do this again sometime! I'll just have to be more careful the next time I steal a pair of her panties... or will I?

All I needed was about an hour more of sleep but my stepmother insisted it was time to rise and shine. Oh I did rise, but not the way she wanted me to. What was I supposed to do? She came in my room to wake me dressed only in a clingy t-shirt and tight panties. My step mother is one hot woman and not much older than I. Of course my dick stood straight up in morning wood glory. She did not approve of my erection on her behalf and exclaimed I was to be punished by spanking. I'm eighteen, and way to old for spankings! The only reason I positioned myself over her sexy knees is I was even more turned on at the thought of lying on her naked legs. She is the one who wanted me bare bottomed so what could she expect but a little pre ejac leakage on her behalf. This discovery only disgusted her. She instructed me to lie over her knees again as she administered heavy handed slaps to my ass. I actually think she was enjoying slapping my ass and may have felt some guilt as she offered me milk and cookies instead of going to school today. I have such a huge crush on her. Now I have to think of something else to disappoint her with so I can be punished again, and again.

I lead such a lazy life. I find a guy with a big heart and a big bank account to match, tell him how much I love him then next thing I know, I'm his wife. It's pretty easy to be taken care of. I mean, why would I want to waste my sexy self on someone who was poor? I want things, lots of things. I like to drive expensive cars and wear cute designer clothes. I find myself often bored though. My husband works long hours to buy me every thing I ask for. He is such a good husband to me and a great Dad to his two boys. Its kind of weird being a step mom to two guys who aren't much younger than me. They are pretty good guys but I do find them looking at me with a little lust sometimes which can be uncomfortable yet enticing. I decided to give them a fun fantasy one day with a generous reward for the winner. We were all sitting around the house when I came up with a fun contest for the two of them. I would jack off both their cocks at the same time and who ever could hold their cum in the longest gets my old BMW. Their dad is buying me a new one soon since my BMW is now almost one year old. This game will satisfy my curiosity of wondering if these guys are hung like their dad, plus it will give us all a bonding experience I think. Their dicks were hard for me even before I pulled them from their pants. I knew they liked me but I didn't think they liked their stepmom this much! I loved having them both in my grip simultaneously. I must admit I would have like to ride them both up my tiny twat. I feel I have to at least save that for their father though. I showed them my tits their dad bought for me. They both stared at me, not saying a word. I was enjoying how much control I had over them. I saw their cocks bounce when I took my panties off and bent over to show them my puffy pussy. I teased them that they may get to fuck my pussy like their dad does sometime. I could tell they were having a hard time holding their load back once I got naked. I decided to really go for the one who’s dick was sticking straight up for me. I knew neither of them wanted to give up their cum first since there was a new car for them riding on the line. Secretly I wanted the smaller dick son to win the car because I already had plans in my mind to fuck the larger dick son. I would give up my pussy to his long straight cock everyday if he wants. I think my pussy is a much better prize than my used BMW. I milked the smaller dick of his cum so quickly he probably forgot he was supposed to be holding it back. I salivated at the thought of bouncing my pussy on the supposed loser son. Hell, I should just give the keys right now to the winner so he can go for a drive in his new car while the loser and I fuck like animals in his bedroom while the house is empty. I'm so glad I came up with this fun game for the boys and now I get a big cock and money all from the same family.

I'm almost too old to be vacationing with my parents but they invited me along last minute on an extended weekend trip to Mexico and I couldn't resist. It's never a guarantee if I'm going to hook up with a girl but with my step-mom around, something fun is sure to happen. No more had we settled in our rooms and had a few minutes at the pool when my step mom and I decided to go back to our rooms to get ready for dinner. My dad was in the lobby getting a rental car set up and my step-mom was putting her make-up on. I couldn't help but stare at her and her perfect lips, wishing they were wrapped around my cock. As my dick began to swell I had to rub it in hopes she would have the same thoughts and sneak a quick hand job in before dad came back to the room. It doesn't take much persuasion because my mom is quite the flirt with me and lives to make me and my dad happy. I waited patiently while she applied her red lipstick, smacked her lips together, I'm sure just to tease me, and then instructed me to the sofa. She looked so pretty in her new vacation dress. I felt like the luckiest guy to be laying there with all her attention on my swollen shaft. With expert hands she applied coconut oil and began what I needed so badly from her, a hand job. There is nothing better than being able to lie back, relax and think of nothing but how deliciously great my cock felt at that moment. With each of her firm strokes my head was being sent to places far from that hotel room couch. Her touch is heavenly. Not only did she stroke my shaft with her hands but she pulled her dress down to get a few good minutes of titty fucking in. We were taking a bold chance here half naked together with my dad only a few floors beneath us in the lobby, we hoped anyway. She was talking so dirty to me to get me to explode for her. She asked if I ever touch myself while listening to her and my dad fucking back home. Of course I do, it's like having live porn in the house except using my imagination to match the sounds they make. I wish I could fuck my step-mom like my dad does. At least I get my cock cranked pretty much whenever I want it, which is not a bad thing at all. She started to ask for all my nasty goo, giving me permission to release any tension I hold thru my dick spit. I gave her all I had, she drained my balls completely. As my head was reeling she reminded me that tonight at dinner we can smile at each other but not to give anything away about the stuff she and I share together. No way am I going to fuck this guaranteed go to.