I have a problem…there’s this guy and we’ve been talking for a while, but things are getting serious. I’ve never done things like that before. I have no idea what to do and I’m freaking out. What if he thinks I’m bad? I don’t know how to touch his cock, suck it, or fuck it. I’m still a virgin. What should I do? Really? You’d help me? Oh that would be amazing. I’m sure you know tons of things that you could teach me. Thank you, thank you so much Stepmom.

GIRL GIRL, INSTRUCTIONAL, KINK, MOMMY ROLEPLAY, STRAP-ON

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Your mom calls you into her bedroom to have a talk with her while your father is out and its just the two of you. She really wants to talk to you about something…..Your mom knows your headed off to college in less then a week and she just realized shes never given you the sex talk before. She wants you to be informed on how to be protected with sex and how to please a woman properly. She explains that she knows when your in college theres going to be girls everywhere and your probably going to be having lots of sex and she wants to make sure your prepared. She also explains that she and your father are really hoping you get a nice stable girlfriend in college and that maybe teaching you how to please a woman in bed and informing you about sex might help your relationship with your future girlfriend be more longer lasting as many women feel unsatisified in bed because there man cums too quickly. Your mom explains that theres many things she can teach you, like how to eat out a woman, how to hit her G spot etc…..but today mommy wants to teach you how to edge yourself. She shows you how to edge yourself and how YOU can masturbate properly to make yourself last longer in bed with the next girl you decide to fuck. Your mom jerks you off with her hand, then she moves to blowjob and lastly tittyfucking. She wants to see how well you can restrain yourself with cumming. In the end you suprise mommy with a cumshot while she tittyfucks you.

MOMMY ROLEPLAY, CUMSHOTS, INSTRUCTIONAL, MASTURBATION ENCOURAGEMENT, TITTY FUCKING

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“Hey, so how was your day?” the babysitter had greeted you warmly when you came back from school. “That bad, huh?”
Sonia tried to make you feel better. Although it was still just the beginning of the school year, you were already starting to have girl trouble. “Oh, gotcha. So, what’s the trouble? Are you just really awkward or are they mean? Or…?” she tried to help. “Oh, just don’t know how to…you know you can talk to girls like normal people. But you mean the ones that you like?”
You had an extremely difficult time flirting with girls. You didn’t know what to say, how to act, and you often embarrassed yourself because of it. “To be honest, there’s no magical secret for you,” Sonia explained. “I mean, I could give you some tips to at least boost your confidence – confidence is a big key. Confidence vs. cocky.”
Sonia then went on to tell you a few pointers on how to talk to girls. “I mean, if you want,” she proceeded to say, “I could show you the way I like things and the way I know a lot of girls that I’m friends with like. Yeah? Okay, yeah, if you’re cool with that. Maybe don’t tell your mom and dad? Just keep it between us – I hate to see you so sad. I want you to feel confident and secure.”
She started off explaining kissing while she stripped down. Her fingers caressed her pink, pretty nipples, showing you exactly what girls found pleasurable and how they liked to be touched. “Just less is always more, especially at this age when everybody’s hormones are going crazy and everything is sensitive,” she told you. “Do you wanna try? Yeah, see? Good, nice and gentle.”
Once you understood how to touch boobs, she explained how to kiss and suck them. “Imagine like a snake with the tongue out,” she said as she flicked her tongue for demonstration. “Do that kinda stuff on nipples. The lighter touch will get things going. Again, I can only imagine what porn has taught you about vaginas, but probably not anything you’re gonna wanna do with your girlfriends, so…”
The babysitter stripped down completely, exposing her bare, shaven pussy to you. She explained the different parts of the vagina, then introduced you to the clit – “the magic button.” She showed you how to rub a pussy, how to warm a girl up, then talked about how to lick a pussy. “Always listen to her breathing, to her body – try and play along. Everybody is different. So, do you wanna try?” she asked.
“I think you’re going to be just fine,” she comforted you as you ran your wet tongue against her pussy. Once you got a feel for how that worked, she moved onto the next lesson – sex. “Oh yeah, you’re hard,” she giggled, “that’s good. I love a man who gets hard from licking vagina. Alright, ready? I’m just going to stick it in…”
“Yeah, go nice and slow to start it, you don’t have to rush it,” she instructed. “This isn’t a porn, this is real life. You’re just here to make you both feel good. Yeah, you’re getting close. I know, it’s okay, it’s a lot for your first time, go ahead.” She told you that it was okay to cum inside of her, so when you were ready, you filled up her tight pussy.
“Oh wow!” she smiled. “There you go. Wow, that was a lot. Okay, so? You feel a little better now, a little more confident about going to school and talking to girls? You got this.”

BABYSITTER, OLDER WOMAN / YOUNGER MAN, VIRTUAL SEX, REDHEADS, SEX ED, INSTRUCTIONAL

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Your best friend’s mom is peeing in the bathroom when you decide to get a little peek. She’s so pretty, it’s hard not to want to look at her, even when she’s doing something like that…problem is, she caught you! Still, you couldn’t stop watching. She told you to leave, even, but you were rooted to the linoleum, watching her cover her privates and repeat that you couldn’t be in there…but you’re just curious, you just want to know what’s going on! And when she realizes that’s the basis for your ongoing stare, she decides to teach you something.
She leans back, pulling her jeans down to her ankles and gives you an in-depth anatomy lesson. She’s shocked that you haven’t had this in school yet, and she goes to work informing you as best she can, working from her clitoris down, touching and rubbing herself while your young cock begins to stiffen. She works two fingers into her vagina and starts to move them in and out, rubbing her clit while she asks if you’re starting to get excited. There’s no hiding it, of course, and she tells you to take your penis out and touch it.
“It’s ok, sweetie, just take it out and touch it like you do when you’re alone in your bedroom,” she tells you, “just promise not to tell anyone about our little lesson, ok?” You agree, taking out your rock-hard erection as she instructs you to stroke it, fingering her pussy and rubbing her clit while you masturbate for her, your best friend’s mom! She pulls up her blouse and opens her legs, giving you a gorgeous view of her body as she leans forward and asks if you’ve ever had someone else touch you like that. You tell her no and she grins, reaching forward to stroke you, bringing you closer and closer to orgasm as she tells you more and more about sex and sexual slang, telling you that you’re going to “cum” for her. You get that tingly feeling and she quickly grabs a piece of toilet paper, jerking you to orgasm onto it.
She tells you to go wash up, and you leave the bathroom to her panting and trying to compose herself. …behind closed doors, Bettie takes the toilet paper, covered in young cum, and sniffs it. She brings it to her mouth and rubs the young sperm all over her face before rubbing the remains across her pussy, fingering herself with the virile jizz of her son’s best friend! She fucks herself to an intense orgasm before wiping the sperm off her face and flushing all the evidence!

MILF, VIRTUAL SEX, HANDJOBS, MASTURBATION ENCOURAGEMENT, INSTRUCTIONAL, MOMMY DOMME

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“My mom moved in with me about a year ago and started wearing pantyhose daily about three months in. After a few of my girlfriends were talking about how I had a nine inch cock. My mom casually said I can confirm. I was simultaneously aroused and ashamed. We were going to watch a movie and I wanted to rub my mom’s feet because I thought it would give me “masturbation material” later. Just asking lol. She actually said yes because the movie was Cleopatra (over 5 hours!), After an hour she let me off and simply rested her ethereal pantyhose clad feet on my inner left thigh. The side I hang my cock. In slow motion I saw her feet come closer and my cock expanded to feel her feet come to rest on it. After about another 15 minutes my mom was so into the movie she started rubbing her feet together on my thigh more precisely my throbbing cock. I got a world class view of her pantyhose covered legs and ass. Even some up-skirt of her gusset. I was staring at her feet the mostly her feet seemed to be caressing my cock. She caught me looking and said “NO!!! my feet stay there for the entire movie!” Her toes twitched and pinched the head of my cock and I came one of the hardest times I ever had. I came at least five times by the end of the movie. I felt a lot of shame when her feet moved away and I saw a string of cum from the cock head in my jeans going to the bottom of her pantyhose encased foot.
I kinda want to watch Cleopatra again lol. I wanted to get a custom where I can basically get a little — during the movie and after “cast” said custom to the screen and have you tell my mom about that and say I masturbate with her worn panties and pantyhose. Confessional and that I want footjobs from my mommy and for her to suck me off as she does the footjob. Also that I want to go balls deep and hit the back of her uterus and paint it white with steamy jizz ropes.*
I want you in pantyhose and wear them throughout even if it ends with you just in pantyhose lol. Maybe therapist like clothes to start.
I just imagine you starting seriously slowly revealing the fucked up nature of my feelings and what happened (5 minutes or so.) revealing how bad I want to get a footjob from my mommies pantyhose clad feet while she simultaneously leans over and sucks my cock. How I jerk off in her pantyhose and panties. Sometimes sucking her cum/discharge out of the pantyhose and panties first after I massaged her pantyhose covered feet for multiple hours. Presumably making her wet or actually coming. What happened watching Cleopatra… and why I wanted to watch it again. How fucking her through her pantyhose would be a great bonding experience! Nothing better than going balls deep in your own mother hitting the back of her uterus and eventually erupting a massive load of millions of sperm frantic to impregnate mommy… if she can even get pregnant. According to our deal I have to get her pregnant and if she can’t well… I have to keep trying a few times a day anyway.”

TABOO, MOMMAS BOY, PANTYHOSE/STOCKINGS, INSTRUCTIONAL, PANTYHOSE FOOTJOBS, CONFESSIONS

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Your mom found the dirty pictures of those hot guys you hid in your room. You get really embarassed and worried that she’s not going to accept you. She quickly reassures you that you’re not in trouble at all. Your mom is so glad that you’re learning more about yourself and your sexuality. She’s so proud of the boy you’re growing up to be! The reason she’s come to talk to you today is because she wants to teach you about boys. She says if boys are going to be something you’re pursuing, you need to know what they like! She pulls out two dildos of different sizes and proceeds to teach you how to please them.

TABOO, DILDO SUCKING, INSTRUCTIONAL, TEACHER FETISH, MOMMY ROLEPLAY

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