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Chapter 2 by Jdoe201207 Jdoe201207

What are your embarrassing/ humiliating naked stories?

Blackmailed into exploring kinks

Every girl has a friend they share everything with. For me that girl is Jessie, a girl I’ve know all throughout high school and is now my roommate in college. We’d give each other relationship advice. That included sex advice and we’d even help each other take nudes for whoever we were dating although that only happened a couple times. During one of our talks about sex, what we liked and what we didn’t, my roommate had a lot to talk about and I didn’t. I hadn’t been with a lot of guys, guys never seem to approach me and if they do they always seem way to cocky. They guys I have been with we’re boring in bed normally just missionary position sex everytime. Jessie on the other hand was normally very open to guys and expressed things she wanted to try. She’d try about every thing once, whether it was a multitude of positions, sex outdoors, three somes, domination both ways, and a new one lesbian sex. That last one is the one she dropped on me mid talk and that’s where speaking up started the snowball. I said wait so your bi now? Jessie said I she might become lesbian if the sex was consistently that good. That’s when I kind of spilled the beans because Jessie knew I didn’t have much sexual experience but she didn’t know how bad. I told her about how I’ve only had missionary sex and had never explored any kinks. Jessie being the assertive person she is said maybe we can do something about that. Why don’t you try masturbating to something new tonight. I don’t like to masturbate I just can’t get in the right mind set I told her. She said then why don’t you let me help. I was kind of taken back but my heart jumped in kind of a excited way but also scared. I said I don’t know I don’t want things to be weird between us. Jessie said she if I ever wanted to stop we could just stop and that it would be better to try this with someone I knew then just a random person. We went in her bed room and she got a dildo for me to use. But I knew I was too dry down there, because I was scared and had no stimulation. Jessie again took the assertive route and started pullin my clothes off. When I hesitated to use the dildo she said here I’ll help. She grabbed me and **** me to play down and started rubbing my clit and eventually I got wet and she smiled at me. Still in a dominating manor she pulled me up off the bed and then she laid down putting the dildo on her crotch as if it was her dick and she said now straddle it. I was scared but I kind of wanted to try to I did. I started going slow and Jessie started saying that she wanted to hear me moan and that I need to let loose. I couldn’t I just didn’t have it in me,I thought, I’m just not like that. Watching me timidly ride the dildo with no sound of pleasure Jessie started bouncing every bounce sent the dildo in and out of me. It started feeling really good but I was scared and was starting to get embarrassed that I was even letting this happen. So I just send no I can’t do this hand hooped of the bed and left. The next day we talk and she asked if I was okay and she was sorry for moving too quickly. I told her it was okay and shyly told her that it was the most exciting sexual experience I’d had seen I’d lost my virginity. She was confused and asked why would I stop then. She thought it was because of her. I quickly told her that I was just scared and I don’t like new things. I told her how I’ve had a lot of fantasies but I’m too scared to explore them. Jessie looked at me and said she had a idea and asked how bad I wanted to figure out what kinks I like. I let my desperation show and said I really want to know but I can’t get myself to try anything new. She looked at me and said that ends today. She said “for the next week you’re going to try every kink I can think of or else”. I said or else what. “Or else I’ll Show your nudes I took of you to everyone I can, I’ll post them on social media, I’ll show them to your classmates, maybe I’ll even make you a tinder with all the profile pictures being nudes so everyone in the university area who has tinder will see them”. I said “you wouldn’t ever do that to me” as I weirdly fell some sexual excitement but was still frightened. Jessie quick pull up a picture of me in the doggy position, back arched so you could see my ass and vagina from the back, but infront of me was also a mirror where you could see me biting my lip and my tits hanging down. She has it one click away from posting and said also look at what profile I’m using. It was mine she has always known my password, but I didn’t think about it. “No no no no okay, don’t post it I’ll do whatever you say for the next week.

What does Jessie have in mind?

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