Babysitting a Teen Girl Blacmail

I'm an ordinary 60-year-old man named Roy who experienced a weekend out of the ordinary a few months ago. The following story is what happened the second night babysitting. To understand the story fully, I recommend you to read my first story, "Babysitting a teen girl".

When I wake up on Saturday morning, I'm a little worried that Sue or her mother Lola will behave strangely or avoid me, but everything is as usual, except I see no Lola. When I don't see her for breakfast, I start to wonder what has happened during the night.

I tell Sue that I heard voices during the night that I thought was my wife. Sue explains that her mother came home during the night to fetch something she had forgotten, but needed at the spa. She did not mention in any way what had happened I my bedroom during the night. She just points out that her injury feels much better, thanks to the massage.

Sue says that she has her own plans for the day which include studying and meeting with some friends. I plan to go to the gym, and take the opportunity to sneak into a pharmacy to buy lube to masturbate with. During the day I also call my wife Olivia, who is clearly feeling better. I manage to convince her again to stay at home and avoid several hours on public transport. It is nice to babysit alone.

Sue and me meets again in the evening and decides to watch a movie, which turns out to be both good and romantic, with lots of hot scenes. When the movie is over, Sue starts to cry and sob quietly. I try to comfort her the best I can, and ask her to tell me what is making her cry.

Sue tells me the same story she earlier told my wife, "When I try to flirt, my clumsy conversations always end with a misunderstanding and me feeling as a total failure." She continued, "I feel stuck in a bubble of insecurity, but I want to experience that magical feeling of being desired, and of being intimate and have fantastic sex, like all my friends." She also tell me that she probably is the last virgin in her class.

Sue says with a soft voice, "I have finally found the right person to try to have sex with." I made the mistake to ask her who that person was. Sue directly hugged me tight and whispered, "I am attracted to an older man by the name of Roy and want to have sex with you!" I was stunned, and could not think straight or even talk.

When I'm still frozen, Sue slowly presses her warm lips against mine and press her tongue into my mouth. It makes my brain come to life, and I politely push her away from me. In a firm voice, I explain to Sue that I can't have sex with her because I'm not going to cheat on my wife.

With tears in her eyes, Sue tell me, "I saw you having sex with my mother Lola late last night, and that I was very jealous. I try to argue that I dreamt I had sex with my wife last night, and have no memory of having sex for real. Sue shows me a photo on her phone where Lola is riding on my dick, and threatens to send the photo to my wife.

I was stunned and needed a minute to think alone, so I told Sue that I had to go to the toilet. When I got there, I locked the door and laughed for myself. Sue was trying to blackmail me, to do what I dreamt of doing, and the only two problems was to have her delete the photo, and to never tell anybody about me fucking her. If I am lucky, I was looking forward to some great sex with the next until virgin Sue. To be prepared for a long night of sex I took a tablet of Viagra from the bathroom cabinet.

When I arrive back to the TV-room Sue is sitting in the corner of the sofa sobbing calmly. I sit down just beside her and tell her that she is stunningly beautiful and that I want her to delete the picture first, to get something in return later tonight. She responds with a nervous tone, "I want to experience everything my mother did yesterday." She tells me why, "I didn't see exactly what you did to Lola but I heard her climax at least three times.

After a few minutes of negotiation, we agree that: Sue directly delete the photo and promise to never tell anyone of us having sex, not even her friends. I promise to have sex with Sue in exactly the same way I had with her mother, the night before, and never tell anybody. I also stress that she has to accept all initiatives I take while we have sex, and not refuse to anything that I want to do with her. She agrees, but asks me to be careful with her because she is so inexperienced, and a virgin. I know that she is not a virgin, at least not in two of her tree holes, but say nothing.

I tell Sue to wait for ten minutes and then go to the toilet, take a shower and apply a good smelling lotion all over her body. When ready, she is welcome to come to my room naked. A very happy girl rushed in to the bathroom. I went to the guest bathroom and cleaned my dick and scrotum and smeared them very carefully with a fragrant baby oil that I found in the bathroom cabinet. I also happened to see two bathrobes with long belts hanging behind the bathroom door. It occurred to me, that they might come in handy if Sue proved more reluctant than I hoped. When I came back to my room, I placed the lube on the bedside table next to my mobile phone, took off all my clothes and lay down on the bed naked on my back.

The moon is shining through the window of the otherwise dimly lit bedroom and casts a soft light over my body. I really hope that Sue shows up naked and smelling good. My plan is to make her do exactly what she did the first night, when she thought that I was asleep. That will make her feel secure and in charge. After that I want to use her to my likening, and at the same time get her to accept everything I forced on her mother the night before.

After about half an hour I hear footsteps outside my room, and soon the door opens. Sue I totally naked and look fantastic. Her small firm breasts have rather large and hard nipples that sticks straight out. Nowhere on her body is any hair visible, she has shaved even around her pussy. Her labia hang down a bit and looks damp, I wonder if she masturbated a little before she came to me.

Sue stands by my bed and look at me, probably thinking about what she is expected to do. With confidence I tell her to touch my semierect cock. When her hand starts to approach my cock, she shivers and when her little hand gets a grip of my cock, I can hear her whisper, "I can't reach around". At the same time, I begin to gently massage her sensitive breasts. Slowly and a little awkwardly, Sue starts to jerk my hardening cock, with only one hand. When Sue after a while grab my hard cock with both hands, I hear a deep inhale from her, and she says out laud, "oh how big". She continues to jerk my dick at an increasing pace with both hands.

After just a minute of jerking, I ask Sue to taste my dick. After just a few seconds, I feel her tongue on my glans licking off my precum and then continuing to lick all the way down to the base. At the same time, one of her hands pumps up and down around my cock. I continue to caress her breasts where the nipples now are rock hard. Sue says, "I want to learn to suck, teach me". Over the next minutes, her mouth is pressed further and further down over the cock and she sucks more and more rhythmically. I give her some advice that sha directly use. Sue is a natural cocksucker and uses her lips, tongue and throat better than I have experienced before. It's impossible not to hump against the tight mouth around my cock and I let go of her breasts and starts pressing her head down at a steady pace. I encourage Sue to let my dick in deeper and deeper into her mouth and throat. When two thirds of my dick is impaled, I see Sues eyes starting to tear up. I tell her that she has proved that she is a greatest cocksucker I have ever felt, and lifts her head from my dick.

I lay her on her back and kiss her tears away from her face. I kiss her on her lips and whisper, "you should take your own virginity sitting on top of me". She answers "do you think your big dick will fit in my tight pussy". "I know it will, if you are wet enough". "Lie down next to me and I'll see if your pussy is moist enough and ready".

I lean over Sue and kiss her deeply while my right hand gently caresses her labia. She moans louder and louder as I gently massage around her opening. While I caress her pussy more and more intensely, I begin to gently lick and suck on her peaky breasts. Her pussy is completely slimy, and without me touching her clitoris or even inserting a finger into Sue's pussy, she is approaching her first orgasm. Since I promised her at least three orgasms, I continue my massage of her labia and breasts until she comes in a strong orgasm and screams straight out. "I love you Dick, I promise to do anything you want tonight!"

After a minute of rest, I tell her to straddle me with her back to my face. To have a great view of her moist pussy and tight asshole I turn on the bedside lamp that shines brightly right on her ass. Resolutely she directs my hard cock towards her tight pussy and slowly starts to lower herself, a little rocking. Sue's whole body shakes when the glans is pressed into her pussy with a plop. She continues to press down a bit, until barely half of the cock is inside. The squeezing feeling around my cock, in the slimy hole is the coolest thing I've experienced.

To never forget this amazing moment, I carefully take my mobile phone from the bedside table and start filming. She continues to rock up and down, in her squatting position, for a few minutes with half of my cock pressed in at its deepest. Suddenly, she stops and sobs, "it´s too big, my pussy is too tight". My quick response is "Remember that it's you, Sue, who are forcing me to take your virginity, not the other way around". Her answer, that I catch on the video is, "Yes, blackmailing you is apparently the only way to get rid of my virginity, now I want you to push your cock to the bottom of my pussy, even if it hurts"

I discreetly stop filming and put my mobile phone back on the bedside table, while I grip the lube. I firmly tell Sue, "lift yourself off my cock and lubricate it properly and then try to push it in deeper when it's really sticky." She lifts her ass up and sits on top of my chest. When she bends over to lubricate my cock, her buttocks are parted and her tight anus comes just inches from my mouth. I can't help but stretch my tongue out and slowly lick her anus. Sue jerks and begs me, "Stop, it feels weird and disgusting".

When she is done lubricating my cock, she once again directs it towards her tight pussy and slowly starts to lower herself. This second time she uses more force and has soon managed to push the whole cock into her pussy. Sue moans, "I was able to get your huge cock to the bottom of my pussy, but I feel overstretched and completely full". After a minute of stillness, Sue slowly starts pumping up and down all the way to the bottom of her pussy. I understand from her moaning that there is no pain, only pleasure on an increasing level. As she pumps up and down in a steady pace I have a perfect view over her tight pussy around my thick shaft. I see her sticky pussy lips and her tightened anal, that I'm planning to fuck later. It, is a sight for gods in the bright light from the bedside lamp! Her orgasm is slowly but surely approaching and when she finally explodes, she tries to stifle her screams as best she can, and keep looking up at the ceiling. It gets really sticky around the root of the cock from her mucus.

Sue doesn't resist the slightest when I lay her down on her side with her back to me and start pumping slowly into her tight pussy in spoon position. After just a few deep strokes in her pussy, she starts to push back, which means that I clearly drive my cock to the bottom of her pussy with each thrust. For the next five minutes, I pump hard into her dripping wet pussy. Her moans get louder and louder and when I start to feel a twitch in my scrotum, I start an intense massage of Sue´s clitoris. At first, she tries to push my hand away, but I continue to firmly rub her swollen clit, while fucking her at maximum pace. The pleasure overwhelms her, and a sudden, intense orgasm rack her body. Her legs cramp, and her whole body shake. Her clenching orifice become painfully tight, constricting around my cock like a vice. As a result, my hot cum is pumped deep into Sue´s stretched pussy, while her own intense third orgasm continue to create cramps and pauses in breathing. After a few minutes of silence, her and my own, panting begin to decrease in intensity. Sue in her relaxed state says, "thank you Roy, you gave me a fantastic memory of my first intercourse, I promise never to tell anyone".

I'm starting to think about what our final agreement, as a result of Sue blackmail. - I promised to have sex with Sue in exactly the same way I had with her mother, and stressed that she has to accept all initiatives I take while we have sex, and not refuse anything, which she accepted. - Thoughts about the possibility to take Sue´s anal virginity, and the Viagra, make my cock grow harder again inside her soaking wet pussy.

In my most firm voice I say "We are far from done yet, your mother had at least one more orgasm". Sue starts to protest and says, "Please, I can't cum anymore, I need a break. My pussy is sore and it can't withstand any further fucking". I tell her that there are other ways to give her one more orgasm, and that she has to comply to our deal. Sue reluctantly admits that she promised to do everything I want, and did with her mother. She says: "I've already experienced everything I've dreamed of in the sex area, what else did you do with my mother?"

I pull my growing cock out and turn Sue around so that she is lying on her stomach, and then I lift her fit ass up so that she is on her knees, but with her upper body still down in the bed. I slap both of her buttocks quite hard with an open hand and in a firm voice say, "I spanked your mother to force her to accept everything I wanted. Tonight, it is your turn, comply or there will be lots of spanking". After a few seconds of silence except slow sobbing, Sue replies exactly as her mother the night before, "I promise, do what you want, but don't spank me anymore".

To prepare Sue for what I am planning, I start licking her slimy pussy with my tongue at regular intervals. Every now and then I lick all the way up to her anus. She moans contentedly all the time but twitches every time my tongue touches her rear hole. It smells and tastes like she's prepared herself well with creams. Sue says: "I never dreamt of being licked, it feels wonderful, but kinky". After a while, I concentrate my tongue more and more on Sue's tightened anus and push a finger into her pussy, which is getting slimier and slimier again. Sue tells me, "Stop, you are disgusting to lick me in the ass." I tell her, "If you don't comply, I will slap your ass again."

Her breathing is very tense, and when I ask her in a firm voice to pull her buttocks apart, she takes a deep breath. Without hesitation, she brings both her hands back and pulls her buttocks apart, causing her pussy to open and her tight anal opening to be fully exposed in the sharp light from the bedside lamp. I can't help but push my tongue at her increasingly soft anus, while fucking the pussy hard with two fingers. Gradually I manage to get the tip of my tongue into her anus.

Without pardon I push my cock into the bottom of her inviting and soaking pussy, and start to fuck her slowly from behind. At the same time, I manage to push a fingertip in to her tight anus. Sue is probably only dimly aware of my finger wriggling around the tender dimple of her anus. For a few minutes I continue to fuck her slowly while moving my finger in and out of her anus at an increasing pace. The way I gently pett her shy, scared butthole with my finger must feel foreign and uncomfortable, and Sue protests: "I haven't even thought about allowing anyone to touch me there, but it is surprising nice to be teased in my forbidden hole".

Sue moans more and more intensely, which makes me add another finger to her anus. The other finger meets greater resistance. Sue whispers almost inaudibly, "be careful, but do what you want. I want to learn everything". Suddenly it hits me that Sue likes to have my fingers in her ass, and that my dream might come true without having to spank her more or tie her up.

To prepare her as well as possible, I spit a large lobe on her anal and insert a third finger into the tight hole, which now is really tight around my fingers. Sue moans and whimpers at the same time. She moans in time with my slowly pumping cock, while the whimper seems to be connected to my stretching fingers in her anus. After a few minutes of stretching, the whimper decreases and it feels like her anal is ready for my thick cock.

I turn Sue around on her back while I put a big pillow under her ass and say: "Now I'm taking your last virgin hole, and to make it easier for you I'm going to lubricate my cock with lots of lube". My hard cock doesn't really need any lube as it's really sticky from the slimy pussy, but I apply it anyway. After stretching one last time with my fingers, I press my plum-sized glans harder and harder against her anus, which initially bravely resists. Sue, holds her knees tight to her breasts to keep her butt cheeks parted. When she feel the increasing pressure against her virgin asshole, she looks afraid. My dick surely looks, and feels, massive compared with her tiny anus.

In a panic, she tries to scrabble away from my thick cock, but I hold her in place with both hands pressing her legs down to her chest. Sue yells, "Stop! Not your huge dick deeper, it hurts!" Sue cries, flailing around beneath me, trying desperately to escape her impending sodomy. I say nothing as I attack her tight hole with the blunt end of my dick. At last, my pressure opens her puckered opening just a little, and a burning sensation flashed up Sue´s spine, causing her to scream.

After half a minute of increasingly hard pressing and holding her, Sue relaxes and the tip of my cock is pushed in a bit. As my cockhead pop past her outer tight passage, it took all my willpower not to cum right then. I stay still inside her straining, teenage rectum, seconds ticking by with my heart beat pulsing through my overstimulated dick. When at length the urge to come abated, I resumed stuffing my hard dick into her resisting channel. She wails in agony, hands now pushing hard on my breast as a feeble attempt to halt or slow my thrusts. Sue is now screaming, "Fuck! Take it out, you bastard!", while fresh tears fall down her cheeks. She looks tormented and exclaims in a now squeaky voice, "Ouch, oh, it's too big, gently". My fast response is: "Just bear with it, it'll feel better soon."

I sawed my dick in and out of her hot fundament, boring deeper into her virgin hole with every thrust. Inch after burning inch sunk inexorably deeper into her overstretched rear. When I finally bottomed out in her hot, clasping teenage butthole, I held still, savoring the sensation of being buried in her squirming depths. Sue looks as she has given up, and offers no resistance or even screams anymore. After withdrawing my shaft so that just the tip remained lodged in her anus, I press forward until my pelvis flattened her voluptuous rear. We gasp in unison - me from pleasure, Sue from pain. I pump at a leisurely pace while I pinch Sue's rock-hard nipples. Sue whimpered and trembled while my cock mercilessly reamed her tortured chute. I began thrusting back and forth in Sue's tiny, teenage asshole while she grits her teeth and sob.

I started pumping my full length through her tight orifice while enjoying the sight and smell of my dick plugging the stacked teenager's red, raw asshole. Sue gasped for air, but does not protest while the massive cock stretching her teen anus. She struggles to endure the violation of her rear port, biting down on a pillow to stifle her cries. As I hope I started to notice sparks of pleasure shimmered up through her body, confusing her senses. I gradually increase the speed while taking one of Sue's hands and bringing it to her pussy, where I rub it against her clitoris. After a minute or so, she continues to masturbate herself. Sue moans in a way that makes it difficult to determine whether the cause is pain or pleasure, perhaps both at the same time. As I continuously pump in her defenseless ass, I feel her opening up to me, her exhausted sphincter becoming slack and unresisting. Soon, her sobs turn to moans. To my delight, I realize another orgasm is building inside her.