I became a sissy for my ex
I've been single for a few weeks now. I left a toxic relationship that was fun but definitely had no love for the last few months. It's my fault for not putting an end to it sooner but I really enjoyed the sexual aspect of it.
It all started when I got caught on video sneaking my ex's sister's panties from her dirty laundry. I was looking for socks and convinced myself at that point, I might as well go for gold. Unfortunately her sister had a camera set up in her room and saw me take her used panties to the bathroom - and it's the fastest I've ever cum.
Well that led into more or less blackmail and I became a sub for my dom of an ex. I learned and appreciated so many new kinks and the biggest one I enjoyed was crossdressing and being used. She used to call me a sissy and would peg me, make me worship her, do humiliating things like be her toilet. Eventually she got bored and left and I was torn between relief and sorrow.
That crossdressing kink stayed and I had plenty of toys, outfits and wigs as well as a decent collection of makeup now. I also have a cage I use when I'm feeling naughty and it's becoming more frequent. I tried really hard to get a prostate orgasm but I get too frustrated and end up taking off the cage and finishing the old fashioned way.
I decided I wanted to achieve the "sissygasm" and after a lot of research I figured if someone was fucking me who was big, then I'd cum in no time. I was scared to do something too gay and I didn't want to cross a line but I convinced myself it was worth it. The first step I took was I froze my chastity key in a block of ice. This helped so much because I would ride and ride my toys but want to touch my dick, but I couldn't quick thaw the key in time so I just kept fucking my ass to get any relief. When I fuck my ass I'm usually really hard when I start and it strains against the cage but after a bit I go limp and just ride for the anal pleasure.
The next step was to find someone game. Now that I was super horny I needed release. I got a few DMs on reddit and exchanged a few photos and vids until I found someone interested. He was a bartender, 6'3 and muscled up. His cock was massive and after some more exchanges he said he wanted to use my ass. I tell him about my key and he says to bring it over this weekend. The whole week I was edging to my toys nonstop but couldn't get the release I craved. I would send more videos to the guy and he would encourage me to behave and keep the key frozen. As it approached Friday evening I got excited and nervous.
I got ready for the night. Made sure I was completely shaved, and I wore my one piece fishnet lingerie. I painted my nails purple and put on my pink wig. I put on some short shorts that really made my ass look good and a white top. I have some open toed heels that really pulled the look together. I spent a long hour trying to follow an egirl makeup tutorial. After I was ready I grabbed my chastity key from the pot I was thawing it in and headed over to their place.
When I arrived I got real nervous and thought about leaving. Some people outside were staring as I headed up to his apartment but before I could second guess myself and leave he opened the door and greeted me with a kiss on the cheek. He told me to come in and I did. He saw the key in my hand and took it. His apartment was well kept and the lighting was dimmed low. He had some sort of electronic music playing. As he closed the door he hugged me around the waist and whispered in my ear.
"You ready for your world to change?".
I shuttered and got chills down my neck as he came in to suck on my neck. I started to moan and I was immediately hard against my cage. My nervousness disappeared as he led me to his bedroom. His strong body guiding me quickly.
He pushed me down on the edge of the bed and whipped out his cock. It was as big as my forearm and thick! It was happening so fast but I was so horny from all week that I reached out and felt his balls. So heavy and full and that's when I dived in. I started slurping on his balls like crazy. It tasted freshly clean like soap and I moved up his shaft. I started kissing his length and head started deep throating. I was so horny for cock that I tried my best but could only get halfway down.
He said "Damn baby, you are a good sissy slut."
This made me moan more and I started making the most embarrassing slurping noises. I was gagging and tried to go down even deeper. I had a lot of practice with my ex and her strap on, but that couldn't compare to this. I was feeling so naughty, and I was holding my breath longer each time. I then came up for air but he held my head down and started fucking my throat. I tried to push away from his thighs but he was too strong. I was trying to breathe through my nose but I couldn't and I started to black out a bit, but then he pulled out and slapped me across the face with his heavy cock.
I gasped and coughed for a bit and then he pushed me on my back. I thought to myself that I needed to get out of here. It was really hot but also I was getting kind of scared. I thought if I could make him cum quickly then I could go home ASAP.
He lifted my leg and took of my heel. I could see my painted purple toes through the mesh and he seemed to appreciate it as he started kissing my heels, my soles and went up to my toes. He started taking deep breathes and then he ripped my fishnets to expose my bare toes and foot. I was a little mad at first as my Ex had bought me this lingerie but soon that was forgotten as he was really worshipping my foot now. It felt so good as he was kissing my ankle. I was incredibly hard at this point but I didn't realize it until now. My dick was straining against the cage and I needed release. He spent a long time on my foot and I think it was mostly for him than for me. He didn't even mention he liked feet.
He then put my leg down and took of my other heel. Swiftly, he ripped my shorts down and I felt so exposed. You could see my caged dick and I saw that I had a lot of precum.
"Nice, you're a good sissy. Your clitty is all caged up. Good." he said in a lustful voice.
The praise made me even hornier. I took of my shirt to expose more of myself and I realized I liked feeling vulnerable like this. He grabbed a hold of my cage and it all fit in his large hand. He took some precum that ****** through my cage and rubbed it on my nipple. He went to start on my other foot and ripped that side too. At this point I didn't care and was rubbing my own nipples. I was moaning lost in the moment.
After maybe ten minutes of him worshiping me and I was needing to cum. I didn't care how. I reached for his massive cock and I barely touched it before he slapped me away and that's when he flipped me over with such force that I was scared again. He then ripped my fishnet suit at my ass. Freeing not only my ass but my caged "clitty". He then dove in and started eating out my ass.
"I have to get this bussy ready baby" he said before diving back in.
I lost control and just laid face down and was moaning like crazy. I was sounding like a total girl. I've never been worshiped like this before. Usually with my ex I had to eat her out for hours with few breaks and she never gave me release. If she did, she would ruin my orgasm and let go of my dick as soon as it started to cum - I hated it. But this felt amazing and I started to get emotional about the pleasure. He stopped and I heard a click or snap and shortly felt a glob of lube rub along my ass against my balls and cage.
"I'm about to own this bussy baby. Are you ready to feel a real man? You sissy slut. You want this thick meat don't you?" He said to me with deep conviction.
I shuttered. I was scared now. I didn't want to do this anymore. My clitty was hurting against the cage and I still wanted to be a man. All these feelings were fighting and then I felt his head push in. No condom, just bare skin pushing against my hole. I tighten up but all this foreplay and previous practice couldn't fight his arrival. I lowered my head down into the bed and was starting to tear up a bit as he entered. So much shame overcame me and I didn't feel right but then he pushed all the way in.
It made it harder to feel shame because my body started reacting positively. I was getting a warm feeling deep inside and he stretched my insides. He was hitting me deep and I felt this pressure in my ass that I've never felt before. My dick was starting to shrink and I felt how much precum was left in the cage. I look down and see a big stream of precum dripping on his bed. I could see his balls slapping against mine as he started to pump me. Each pump made me groan out, partly not wanting it but also enjoying the pleasure. I was moaning and subtly crying with each thrust.
I felt like a failure. Like I somehow let someone down. That's when my life changed. He grabbed me by my throat and lifted my head up and gave me words of encouragement.
"It's okay baby. Let me take care of you. You're my sweet sissy girl and I'm gonna use that bussy. This is what you were meant to do, take this big cock baby. "
He started pumping harder and began to tongue me. I started kissing back and he pulled away to say, "good girl".
That triggered something as I began to kiss him back. I was whimpering at this point with each thrust, sounding like a bimbo in a porno. It clicked that it was okay to do this, that I could surrender myself. This is my one life so let me enjoy it how I want. I gave in. I'm a sissy. I'm his sissy. A sissy slut who wants to be bred. I started throwing it back against his steel rod and I started curling my toes. I felt a warm pressure inside my body and that's when it happened.
I shoot my eyes wide open and let out a deep primal sissy moan as I feel it slowly building. My whole body is shaking and I feel so warm and pleasurable. It's a feeling I've never felt and then my clit starts shooting cum. It starts pouring out like a fountain and then I start spraying all over my cage and his bed. It felt like an even stronger orgasm than when I normally cum and I was nonstop shooting. I came so much when I looked down there was a large standing puddle beneath me.
"You're such a a slut" he roared as he flipped me over.
I could only moan out. Now on my back I needed it all. I wasted all this time worrying. Now I'm lost in lust.
"Fuck me. Please. Fill me up." I start begging.
He took that as a queue and took my leg and lifted my foot into his mouth. He was trying to remove the paint off my toes as he started worshipping them. This made me even hornier and I was riding his cock with each slam. I was flicking my nipples and was moaning. After my first orgasm I felt even hornier.
"Please. Ugh. Fuck me. Fuck me. FUCK ME. OOOOOUUUGHHHH, FUCK CUM. CUM. CUM IN ME. OH SHIT. IM CUMING FUUUUUCK" my voice was so high pitched I didn't recognize it.
I was really a sissy now. Then I felt his member engorge and he started to pump and fill me with his seed. I felt the splatter hit my inner walls hard and it was so hot, I had another sissygasm. No cum from me this time but I was shaking like crazy. My arms were weak and they flopped down at my sides. He came in and kissed my neck and I wrapped my arm around him, giving into his masculinity -allowing myself to be taken care of.
He then scooped his arms underneath me and took me to his bathroom. He put me in the tub and turned on the shower. He directed the water at the wall until it heated up and then he let it run on my body. The warmth felt so good and I was ready to fall asleep. Then he stepped over me. He beckoned with his finger and I sit up and took his softening cock in my mouth. It was still so big and I could taste our juices.
I felt so submissive and I could've stayed there forever tasting his cock. Once it was cleaned up he started to piss and it wasn't the first time I've dealt with this as my ex had a huge piss kink but this made me feel more submissive and I opened my mouth and drank a bit. I felt so slutty and when he was done he slapped me across the face with his meat and it stung, almost felt like a punch. He washed up as I still sat there too weak to stand. After he got out, I then stood up and showered myself off, taking off my ripped lingerie.
After my shower I joined him in bed. Both of us were nude and I thanked him. He said he'll buy me tons of new outfits so don't worry about those. I told him I wouldn't and I soon drifted off to sleep, feeling secure in his big arms.
I woke up first, or not completely first as his member was standing at full attention poking me. I was still horny from last night and my ass was a little sore but it made me even hornier and I straddled him and started slowly working his cock with my mouth. Using both hands and thoroughly enjoying all parts, I was enthusiastic in my cock worship. He then wakes up and starts eating my ass again and I know I'm gonna have a good morning as well.
It all started when I got caught on video sneaking my ex's sister's panties from her dirty laundry. I was looking for socks and convinced myself at that point, I might as well go for gold. Unfortunately her sister had a camera set up in her room and saw me take her used panties to the bathroom - and it's the fastest I've ever cum.
Well that led into more or less blackmail and I became a sub for my dom of an ex. I learned and appreciated so many new kinks and the biggest one I enjoyed was crossdressing and being used. She used to call me a sissy and would peg me, make me worship her, do humiliating things like be her toilet. Eventually she got bored and left and I was torn between relief and sorrow.
That crossdressing kink stayed and I had plenty of toys, outfits and wigs as well as a decent collection of makeup now. I also have a cage I use when I'm feeling naughty and it's becoming more frequent. I tried really hard to get a prostate orgasm but I get too frustrated and end up taking off the cage and finishing the old fashioned way.
I decided I wanted to achieve the "sissygasm" and after a lot of research I figured if someone was fucking me who was big, then I'd cum in no time. I was scared to do something too gay and I didn't want to cross a line but I convinced myself it was worth it. The first step I took was I froze my chastity key in a block of ice. This helped so much because I would ride and ride my toys but want to touch my dick, but I couldn't quick thaw the key in time so I just kept fucking my ass to get any relief. When I fuck my ass I'm usually really hard when I start and it strains against the cage but after a bit I go limp and just ride for the anal pleasure.
The next step was to find someone game. Now that I was super horny I needed release. I got a few DMs on reddit and exchanged a few photos and vids until I found someone interested. He was a bartender, 6'3 and muscled up. His cock was massive and after some more exchanges he said he wanted to use my ass. I tell him about my key and he says to bring it over this weekend. The whole week I was edging to my toys nonstop but couldn't get the release I craved. I would send more videos to the guy and he would encourage me to behave and keep the key frozen. As it approached Friday evening I got excited and nervous.
I got ready for the night. Made sure I was completely shaved, and I wore my one piece fishnet lingerie. I painted my nails purple and put on my pink wig. I put on some short shorts that really made my ass look good and a white top. I have some open toed heels that really pulled the look together. I spent a long hour trying to follow an egirl makeup tutorial. After I was ready I grabbed my chastity key from the pot I was thawing it in and headed over to their place.
When I arrived I got real nervous and thought about leaving. Some people outside were staring as I headed up to his apartment but before I could second guess myself and leave he opened the door and greeted me with a kiss on the cheek. He told me to come in and I did. He saw the key in my hand and took it. His apartment was well kept and the lighting was dimmed low. He had some sort of electronic music playing. As he closed the door he hugged me around the waist and whispered in my ear.
"You ready for your world to change?".
I shuttered and got chills down my neck as he came in to suck on my neck. I started to moan and I was immediately hard against my cage. My nervousness disappeared as he led me to his bedroom. His strong body guiding me quickly.
He pushed me down on the edge of the bed and whipped out his cock. It was as big as my forearm and thick! It was happening so fast but I was so horny from all week that I reached out and felt his balls. So heavy and full and that's when I dived in. I started slurping on his balls like crazy. It tasted freshly clean like soap and I moved up his shaft. I started kissing his length and head started deep throating. I was so horny for cock that I tried my best but could only get halfway down.
He said "Damn baby, you are a good sissy slut."
This made me moan more and I started making the most embarrassing slurping noises. I was gagging and tried to go down even deeper. I had a lot of practice with my ex and her strap on, but that couldn't compare to this. I was feeling so naughty, and I was holding my breath longer each time. I then came up for air but he held my head down and started fucking my throat. I tried to push away from his thighs but he was too strong. I was trying to breathe through my nose but I couldn't and I started to black out a bit, but then he pulled out and slapped me across the face with his heavy cock.
I gasped and coughed for a bit and then he pushed me on my back. I thought to myself that I needed to get out of here. It was really hot but also I was getting kind of scared. I thought if I could make him cum quickly then I could go home ASAP.
He lifted my leg and took of my heel. I could see my painted purple toes through the mesh and he seemed to appreciate it as he started kissing my heels, my soles and went up to my toes. He started taking deep breathes and then he ripped my fishnets to expose my bare toes and foot. I was a little mad at first as my Ex had bought me this lingerie but soon that was forgotten as he was really worshipping my foot now. It felt so good as he was kissing my ankle. I was incredibly hard at this point but I didn't realize it until now. My dick was straining against the cage and I needed release. He spent a long time on my foot and I think it was mostly for him than for me. He didn't even mention he liked feet.
He then put my leg down and took of my other heel. Swiftly, he ripped my shorts down and I felt so exposed. You could see my caged dick and I saw that I had a lot of precum.
"Nice, you're a good sissy. Your clitty is all caged up. Good." he said in a lustful voice.
The praise made me even hornier. I took of my shirt to expose more of myself and I realized I liked feeling vulnerable like this. He grabbed a hold of my cage and it all fit in his large hand. He took some precum that ****** through my cage and rubbed it on my nipple. He went to start on my other foot and ripped that side too. At this point I didn't care and was rubbing my own nipples. I was moaning lost in the moment.
After maybe ten minutes of him worshiping me and I was needing to cum. I didn't care how. I reached for his massive cock and I barely touched it before he slapped me away and that's when he flipped me over with such force that I was scared again. He then ripped my fishnet suit at my ass. Freeing not only my ass but my caged "clitty". He then dove in and started eating out my ass.
"I have to get this bussy ready baby" he said before diving back in.
I lost control and just laid face down and was moaning like crazy. I was sounding like a total girl. I've never been worshiped like this before. Usually with my ex I had to eat her out for hours with few breaks and she never gave me release. If she did, she would ruin my orgasm and let go of my dick as soon as it started to cum - I hated it. But this felt amazing and I started to get emotional about the pleasure. He stopped and I heard a click or snap and shortly felt a glob of lube rub along my ass against my balls and cage.
"I'm about to own this bussy baby. Are you ready to feel a real man? You sissy slut. You want this thick meat don't you?" He said to me with deep conviction.
I shuttered. I was scared now. I didn't want to do this anymore. My clitty was hurting against the cage and I still wanted to be a man. All these feelings were fighting and then I felt his head push in. No condom, just bare skin pushing against my hole. I tighten up but all this foreplay and previous practice couldn't fight his arrival. I lowered my head down into the bed and was starting to tear up a bit as he entered. So much shame overcame me and I didn't feel right but then he pushed all the way in.
It made it harder to feel shame because my body started reacting positively. I was getting a warm feeling deep inside and he stretched my insides. He was hitting me deep and I felt this pressure in my ass that I've never felt before. My dick was starting to shrink and I felt how much precum was left in the cage. I look down and see a big stream of precum dripping on his bed. I could see his balls slapping against mine as he started to pump me. Each pump made me groan out, partly not wanting it but also enjoying the pleasure. I was moaning and subtly crying with each thrust.
I felt like a failure. Like I somehow let someone down. That's when my life changed. He grabbed me by my throat and lifted my head up and gave me words of encouragement.
"It's okay baby. Let me take care of you. You're my sweet sissy girl and I'm gonna use that bussy. This is what you were meant to do, take this big cock baby. "
He started pumping harder and began to tongue me. I started kissing back and he pulled away to say, "good girl".
That triggered something as I began to kiss him back. I was whimpering at this point with each thrust, sounding like a bimbo in a porno. It clicked that it was okay to do this, that I could surrender myself. This is my one life so let me enjoy it how I want. I gave in. I'm a sissy. I'm his sissy. A sissy slut who wants to be bred. I started throwing it back against his steel rod and I started curling my toes. I felt a warm pressure inside my body and that's when it happened.
I shoot my eyes wide open and let out a deep primal sissy moan as I feel it slowly building. My whole body is shaking and I feel so warm and pleasurable. It's a feeling I've never felt and then my clit starts shooting cum. It starts pouring out like a fountain and then I start spraying all over my cage and his bed. It felt like an even stronger orgasm than when I normally cum and I was nonstop shooting. I came so much when I looked down there was a large standing puddle beneath me.
"You're such a a slut" he roared as he flipped me over.
I could only moan out. Now on my back I needed it all. I wasted all this time worrying. Now I'm lost in lust.
"Fuck me. Please. Fill me up." I start begging.
He took that as a queue and took my leg and lifted my foot into his mouth. He was trying to remove the paint off my toes as he started worshipping them. This made me even hornier and I was riding his cock with each slam. I was flicking my nipples and was moaning. After my first orgasm I felt even hornier.
"Please. Ugh. Fuck me. Fuck me. FUCK ME. OOOOOUUUGHHHH, FUCK CUM. CUM. CUM IN ME. OH SHIT. IM CUMING FUUUUUCK" my voice was so high pitched I didn't recognize it.
I was really a sissy now. Then I felt his member engorge and he started to pump and fill me with his seed. I felt the splatter hit my inner walls hard and it was so hot, I had another sissygasm. No cum from me this time but I was shaking like crazy. My arms were weak and they flopped down at my sides. He came in and kissed my neck and I wrapped my arm around him, giving into his masculinity -allowing myself to be taken care of.
He then scooped his arms underneath me and took me to his bathroom. He put me in the tub and turned on the shower. He directed the water at the wall until it heated up and then he let it run on my body. The warmth felt so good and I was ready to fall asleep. Then he stepped over me. He beckoned with his finger and I sit up and took his softening cock in my mouth. It was still so big and I could taste our juices.
I felt so submissive and I could've stayed there forever tasting his cock. Once it was cleaned up he started to piss and it wasn't the first time I've dealt with this as my ex had a huge piss kink but this made me feel more submissive and I opened my mouth and drank a bit. I felt so slutty and when he was done he slapped me across the face with his meat and it stung, almost felt like a punch. He washed up as I still sat there too weak to stand. After he got out, I then stood up and showered myself off, taking off my ripped lingerie.
After my shower I joined him in bed. Both of us were nude and I thanked him. He said he'll buy me tons of new outfits so don't worry about those. I told him I wouldn't and I soon drifted off to sleep, feeling secure in his big arms.
I woke up first, or not completely first as his member was standing at full attention poking me. I was still horny from last night and my ass was a little sore but it made me even hornier and I straddled him and started slowly working his cock with my mouth. Using both hands and thoroughly enjoying all parts, I was enthusiastic in my cock worship. He then wakes up and starts eating my ass again and I know I'm gonna have a good morning as well.
3 månader sedan
