The year was 2011, I had been 18 for a couple of months, a senior at a relatively small town high school and a starter on the varsity soccer team. I had friends in almost every group there was but didn’t really consider myself a part of any of those cliques. I regularly had a new girlfriend every couple of weeks and was an outgoing and extroverted person in my day to day life. What no one knew was that behind closed doors and online I was an attention seeking sissy whore who loved to dress up, tie myself up and chat with men and women online.
I often found myself in chat rooms talking to guys from all over the world and sending them pics of me with a blurred face or no face at all. One night I decided I would be a little bolder. I went onto craigslist and posted a personals ad. This was 12 years ago but I believe the ad went something like this.
18 Year Old Sissy Looking for Master
I am an 18 year old sissy virgin who has never been with a man before. Please come and use me. I need a strong man to take charge of me and have their way with me.
Or something to that effect.
I had a lot of people respond and being completely honest I had zero intention of meeting up with anyone. At this point in my life I had never even been dressed up in front of someone else, much less played with anyone. One guy had messaged me and he seemed different from everyone else. Most people started off with all the things they wanted to do to me or calling me names right out the gate but he had messaged me and talked to me like a normal person. We ended up chatting about fantasies we had and other things we liked. Sharing pictures we had found online of sissy captions and differing things.
After a couple of days of chatting I was texting him one night and he had convinced me to wear panties and edge myself while I was at school the next day. It was a Friday, and I went to each class stealthily rubbing myself through my pants while in class and going to the bathroom at every opportunity to edge myself in one of the stalls. By the time the school day was over I was a horny mess, having leaked precum into my panties all day. I just wanted to get home and play with my little clit till I came.
When I got home, I asked him if I could please play with myself and cum now. He wasn’t my “Master” but I was enjoying allowing him to control when I could and could not touch myself or cum. He told me that he would allow me to cum if I dressed up and sent him a pic of me. I hadn’t posted a pic on my craigslist ad and I had been kind of avoiding sending him one for the past couple of days. Today however when he asked, I was so horny and excited I agreed immediately. I told him that it would be from the neck down though because I was still not ready for that. He said that was fine just to make sure I was dressed and that my tiny little clit was on display.
I was beyond horny. All reasoning was gone from my bimbo brain. I quickly got dressed. Putting on a bra, the panties I was wearing that were soaked in my precum were the only ones I owned. I put on a skirt and a small tank top. I wished I had some stockings but I didn’t so I settled for some knee high socks. I stood in front of the full length mirror in the corner of my room and sent him a handful of pics. Trying to look sexy with my hand and leg placements.
When I sent the pictures I also sent a message begging him to let me play with myself. I was losing my mind with horniness. He told me he had something to do and he would be back in a few but for me to keep edging myself until he returned and then I would be rewarded like a good little girl. I edged myself over and over waiting for him to message me again. I kept checking my phone every 15 seconds, willing him to message me back. Finally, a message popped up. When it did, I stopped touching myself, my heart racing, a nervous sweat broke out and ran down my back as my whole body flashed hot and shivered cold at the same time.
His message said “You make a really good sissy [my real name]. I never would have thought that was you saying all those dirty things.” I didn’t know what to do so I tried to bluff and say I had no idea who that was. That wasn’t my name. He said that yes it was and that was strike one. Two more strikes and he would out me to the whole town. I didn’t know what to do. I asked him why he thought I was the person who I had never even heard of. He said that was strike two. The reason he was able to figure out who I was had been something I had never been concerned about when sending people around the world pics of me.
He had cropped my picture and sent back a picture of the back of my phone. A few guys on our team had let the girls soccer team decorate our phone cases with stickers. The first was my school logo which was clearly visible, the next sticker was of a soccer ball, and the last sticker was the number 12 which was my jersey number. Unbeknownst to me this man was the father of one of the girls on the soccer team and her case was decorated in almost the exact same way as mine. He had gone and looked up the team and found me based on my jersey number. Then he looked at the pic I sent him next to one of me to confirm that I was in fact the number 12 midfielder from the varsity soccer team.
I was terrified. I could not believe that this had happened. My life was over. This man had complete control over me and could out me to whoever he wanted. To make matters worse his daughter was one of the biggest gossips in the school so I was extra scared of her finding out because I knew the whole school would know within the hour.
He told me I would do exactly as he said, I only had one strike left so I better not mess up. I agreed to do whatever he told me as long as he promised not to ruin my life. He told me to go to the city nearby and go buy a wig at the sex shop. I told him I would, but I had no money. I was an unemployed high school student; I begged him not to punish me for not having the money to do it. He sent me some money through PayPal and told me that if he required me to buy something that he would pay for it. He told me to get some heels, stockings, and a chastity cage as well as the wig.
I was feeling very strange, on one hand I was terrified that my biggest secret had been figured out by this man but at the same time I was incredibly horny at the thought. I was also scared of going to the sex shop to buy all these sissy things but the idea of finally owning these things excited me to no end.
I went to the shop he had instructed and went to the desk to ask for assistance. I didn’t want to ask someone to help me but he had made clear instructions to ask and tell them my
Master had sent me to get some things to feminize myself for him. As I said this my face was as red as an apple. I could not believe I had gotten myself in this situation. While I was so embarrassed I wanted to go hide in a hole for the rest of my life I was also painfully horny. I got a pair of 3 inch stiletto heels, some stockings with built-in garter, a long black wig that I would use for the next couple of years, and a chastity cage.
He instructed me to go home and shave myself, he apparently likes his sissies smooth, then get dressed and go to his house. I went home and shaved my whole body from head to toe. I put the new chastity cage on and then I got dressed except for the heels and wig and put my boy clothes over top of my sissy clothes.
He had given me his address, told me to go to his house, kneel at his front door in only my sissy clothes with the key to my chastity cage on my tongue and ring the doorbell. I was really worried about this because I was thinking that his neighbors might see me. I didn’t need to be concerned, as I pulled into his driveway I realized the nearest neighbor was a quarter mile in either direction and that the property was completely surrounded by thick trees. I drove to his house and before getting out of my car I took off my boy clothes, put on my wig and heels. I was so nervous I could barely strap my heels on with shaking hands. I got out of the car and made my way to the front door. I kneeled in front of it, my clitty leaking streams of precum out of my chastity cage, I rang the doorbell sealing my fate.
As I kneeled on his porch I was shaking in fear. What if his daughter was home? Was he married? As I thought about all these things I was getting more and more worried as well as horny. The door opened and I looked up at the man who was in control of my fate. He was about 6 ft 4in tall, not super built but clearly took care of himself, short black hair peppered with gray, he was a very attractive man and I definitely recognized him from school events his daughter had been at. He smiled down at me, reached down, took the key off my tongue and slipped a collar around my neck. He clipped a leash to it and told me to follow him. I went to stand to follow but he put a hand on my shoulder and told me that a sissy like me should crawl unless told she can walk like a normal person.
I crawled behind him into his house, silently berating myself for letting this happen and for not having the courage to say no, a shiver going down my spine as I realized I was more horny than I’ve ever been in my life. He led me to his room and had me get on the bed. He told me how sexy he thought I was. I blushed feeling even more turned on by his words. He tells me that he is going to tie me up now. My stomach was doing flips. I of course said, “yes Sir, thank you,” as there was nothing else I could do. He took my ankles and tied them to my thighs causing my legs to stay bent. Then he tied my left hand to my left thigh and my right hand to my right thigh. He started to touch me, rubbing his hands all over me. He wraps his hand around my throat and chokes me as he leans in, telling me what a good sissy I am and that he wants me to get on my knees and suck his cock till he cums. If I do it well enough he might even let me out of my cage so I can cum.
The thought of being able to cum makes me almost willing to do anything. I slowly slide off the bed and onto my knees. I look up at him and open my mouth and stick my tongue out. “Please Sir, may I please suck your cock.” He chuckles and pulls his cock out of his pants. Its considerably larger than mine, at least 8 inches. He rubs the head on my tongue smearing the precum that leaking out of it. My first taste of cock, just this little taste almost makes me cum in my panties. I lean forward to take it into my mouth but he pulls back and grabs me by my chin. He tells me to beg for him to let me pleasure him. I beg him him “Please Sir, I want your cock so bad. Please let me suck your cock. I want to taste you Sir. I want you to be my first cock. To change my life forever.” He smiles and slides his cock between my lips, I'm on the verge of exploding as I take him inside my mouth. I try to take him into my throat and I gag on him. He's far larger than anything I've ever sucked on pretending it was a cock.
Undeterred I keep trying to deep throat him, gagging over and over, tears welling up in my eyes. I keep sucking him with as much effort as I can, only able to use my mouth since my hands are tied. His moaning spurs me on, I cant believe im making a man moan, that a man is turned on and enjoyed by a pathetic sissy like me. He grabs my head and starts to fuck my throat, im fighting back my gag reflex as best I can so don’t throw up on him. I feel him shudder and moan loudly, as he unleashes a torrent of cum into my mouth and throat. He pulls his still leaking cock out and rubs it onto my face. He tells me what a good girl I've been and that now it's time for my reward.
He takes a pair of scissors outband cuts off my panties. He pushes me down so my face is on the ground and my ass is in the air, I feel something wet and cold touch my asshole. Then I feel his finger press into me, he starts to slide his finger in and out of me lubing up my hole and inside of me. I feel him wiggle his finger and a jolt of pleasure shoots from my ass all the way to my stomach. I let out a loud moan, he chuckles and says “ooo looks like I’ve found your sissy spot” .
He keeps doing this for a minute as I writhe and moan from the intense pleasure unlike anything I had ever felt before, adding a second finger and then a third. He pulls his fingers out of me leaving me feeling surprisingly empty. He wraps his hand around my throat again, choking me and says he has three options for me. The first one is that he just keeps fingering me like this until I cum or he gets tired but I don’t get let out of my cage, the second is that he puts a dildo in my ass and I ride it till I cum but he will take off my cage and use a vibrator on my clit or the third option is I can let him fuck me and he will fuck me till we both cum and he will completely untie me so I can play with myself as much as a I want.
I look over and into his eyes. My whole body is buzzing from the insane emotions and sensations coursing through it. I ask him “will I get in trouble if I pick the wrong one?”
He leans in and says, “no, this is your reward for being such a good girl. Pick whichever one you want.”
I pick option two, I'm not ready to give my anal virginity away. That is a story for later and is another example of how I tend to get myself into bad situations.
He pulls out a dildo that has a suction cup as a base. It's not as big as his cock but it's bigger than my little clit. He slowly slides it inside of me, as the tip penetrates me I let out a moan, he keeps working it in and out gaining a couple of centimeters at a time. With every time he slides back into me I shake and shudder with the intense feeling rushing through me. he continues until he has worked it all the way to the base. I feel incredibly full, moaning and wiggling my ass in the air. He lowers me onto my ass, suctioning the dildo to the hardwood floor.
He starts making me ride the dildo in front of him. I start moaning loudly. He takes my cum drenched panties that he cut off of me earlier and shoves them in my mouth. I can taste myself on the panties, with each thrust inside of me I leak more and more onto the ground. He pinches and pulls my nipples causing me to moan even more while his other hand is still wrapped around my throat. I can feel a tightness growing inside of me as I keep riding the dildo. He helps me balance on the dildo with the hand on my throat, helping me ride up and down. He asks if I want to cum, his hand choking me and my mouth full of panties I can't answer so I nod emphatically moaning “yes please yes” as best as I can.
He unlocks my cage letting my clit pop out. It's as hard as it's ever been in my whole life and it's still not as big as his softened cock. Pulling the panties out of my mouth shoved the shaft part of my cage into my mouth telling me to clean my precum off of it before shoving the panties back in. Then he reaches into his bag and pulls out a vibrator. Putting the vibrator right under the head of my clit. The vibrations turns on and my whole body feels like lightning is coursing through it, my rhythm getting completely ruined as I shake and seize from the vibrations. He choked me harder telling me not to cum till he gives me permission. Hearing this sent me closer to the edge. I can feel that I can’t hold on much longer. I start begging and begging as best as I can. Squeezing my throat even harder and spitting in my face he tells me to cum for him. I keep pumping the dildo inside of me as I explode all over the floor, I keep going and going cumming more and more. The orgasm finally passes and my whole body sags from exhaustion, mental and physical. He lifts me off the dildo and then shoves my face to the ground and demands I clean up my mess. I greedily lick up my own cum until the floor is clean and as I do this he locks my clit back in its cage.
He untied me holding me in his arms and asked if I was ok. I told him that was the most amazing experience of my life. He smiled and said he was happy to hear it because it would become a regular part of my life until he decided he was tired of me. A shiver went down my spine, he still planned to blackmail me.
I asked him if I could speak because I was afraid of saying something that would cost me my third strike. He said yes he would allow me to speak freely. I asked him if he was married, he said that he was divorced and had a few girlfriends but that he was single. I asked if I was going to have to wear the chastity cage every day, he said no that it would only be at night when home and when I was coming to see him. I asked if I was going to be allowed to keep dating, he said yes but only girls he was to be the only man in my life. I asked what if his daughter found out he said that as long as I did what I was told to do that he would make sure no one found out my secret, his daughter lived with her mother so she was not at his house very often. I asked the question I had been building up to. How long would this last? He told me that he would make me a deal. If I was his faithful sissy for one month and did everything I was told then he would stop holding the blackmail over me. if I messed up then he would tell one person every time I messed up and if I ever flat out refused him then he would out me to the world. As he says this my clit starts to get hard in its cage again.
He slid me off his lap and onto the floor then pulled my leash till his cock was in front of my face once again. He looked down at me and said, “suck it sissy.” I of course did as I was told.
That’s the story of the first time I got blackmailed. It was not the last time.