Day 2 Sissy Hotel weekend
This is a continuation of the previous nights adventure
I woke up a couple times in the night with painful sissy cramps in my chastity cage but managed to ride my large dildo till the annoyance passed. I was out of bed and into the shower by 9 the next morning... my brown daddy from the night before was coming at 10 so I quickly douched and shaved and got into my purple thigh highs and my tight purple t-shirt that says sissy on it in large pink letters, I wore a black wig and just had time to get my makeup mostly done when he was knocking at the door. I hadn’t had time to check my doublelist messages yet.
I quickly applied some lipstick and rinsed with scope before answering the door. He hurried into my room and seemed a little annoyed that I’d made him wait... I apologized and asked if I could make it up to him, he slipped out of his joggers and pointed his semi hard dark brown cock at me... I engulfed his cock with my wet mouth and gently stroked his shaft. He again became very vocal and called me his little whore and his cum slut, he moaned as he aggressively began throat fucking me... I gagged and coughed and even puked a tiny bit and it all just made him moan more loudly and grab the back of my head as he deep throat face fucked me. After a little while he pulled his cock free and told me to look in the mirror before he bred me... I stood and saw my make up destroyed and my shirt covered in saliva, I looked like a used up trashy whore and it made me swell in my cage. I fixed my wig and he led me onto the bed and onto my hands and knees in doggy with my legs together and my caged clit pulled back on display, I felt him press his cock against my now very open sissy pussy lips and push himself all the way in before resting with his big balls pressed against my smooth full sissy balls. He pulled almost all the way out and then slammed back in hard, doing this several times before settling into a slow deep rhythm... his balls slapping against my little locked up package with each thrust. He made sure I knew how pathetic I looked with his big brown cock fucking my well used sissy cunt and my little caged clit dribbling away. I was starting to feel like I was going to have a sissygasm when he began to fuck me much faster and grabbed my hips... pulling me onto him hard as he bred me deep. He pulled out and I quickly turned and cleaned his cock with my mouth, making sure to suck every last drop. I thanked him for his load and he quickly dressed and commented on how slutty I looked before leaving, I tried to fix my make up but it was beyond repair so I stripped it right off and then decided while I was not too slutted up to find a sex shop and get a larger plug.
I pulled on some panties to match my stockings and put on some loose fitting boy clothes before looking online and finding a suitable shop a 5 min drive away. It didn’t open for 30 min still though so I decided to check my doublelist messages and could not believe the deluge of replies. Big cities are the place to be for sissy cum dumps apparently lol. Sadly I had not heard back from the huge cock older guy I’d seen the night before and replies didn’t have any pics as I’d requested and there were several that just seemed too shady but one reply was from another East Indian guy asking if I would like to host he and his two friends, he’d supplied a pic with all three of them pointing they’re cocks at each other and I could just picture myself in the middle being a spoiled rotten sissy. None of them had a massive cock but they all put my little fag clit to shame and I had always wanted to be gangbanged so I messaged him back with a pic of me pulling my sissy pussy open in a spoon position and my caged clit poking out between my thighs and asked him to name a time. Then I headed out to the sex shop.
I arrived with still 10min before opening and waited in the parking lot... across from me was an elderly guy who was staring in my direction, I waited for the store to open and wanting to be alone in there I waited to see if he would go in before I finally decided to go. I made my way into the small shop and was surprised to find it very well equipped with larger toys and even a small selection of chastity cages. I asked the clerk where I would find plugs and the large older lady behind the counter kindly pointed them out, I looked over several and had decided on a 2.5” wide plug with a round base when I realized the old man from the parking lot was standing just behind me. I moved away slightly and he motioned towards the package in my hand and asked if I needed any help breaking it in... I blushed and stuttered a little embarrassed, I paused for a second before suggesting he follow me to my hotel and do just that. He agreed and I quickly went to the till and paid, he told me to wait in the parking lot and he came out soon as well carrying a large bag.
He followed me back to my hotel and brought the bag with him as he followed me up to my room, he was grabbing my ass all the way up the stairs and found my caged up clit as I we made our way through the door. He was not very happy I was caged and asked me to take it off but I hadn’t even brought the keys with me and I had no desire to be uncaged, he complained a little more but I slid out of my boy clothes and he was soon greedily eating my sissy pussy and fingering me. He reached into his bag and pulled out a large tapered black dildo that looked like it went from about 1.5” wide to around 3” wide. He pushed it in slowly at first but soon realized how open my pussy already was and was not gentle as he gave my pussy an unbelievable stretching with that huge toy... I moaned and at times cried as he used me until he was able to pull the toy loose and slide his whole fist in with ease, he punched fucked my pussy for a while before pulling his semi hard cock out and sliding it inside my now loose cunt. He never seemed to get hard but came a respectable load on my back before using his cum to lube my new plug and filling me up with it, it was luckily big enough to stay even after all that stretching and I lay there worn out for a while as he dressed and left, leaving the large toy he’d bought on the bedside table.
I checked my messages and saw that my gangbang crew wanted to come for 8:00 so I confirmed that and replied to a black guy who looked to have a nice big cock and a shorter bodybuilder guy that never sent a cock pic but looked so dominant I didn’t really care. Then I smoked a joint and put on my makeup while watching sissy hypno on my iPad. The bodybuilder guy got back to me right away and could head over ASAP so I sent him my address and he was there in about 45min.
He complimented me on my outfit and was surprisingly soft spoken and gentle for a guy of his stature, every muscle was incredibly well defined and his abs were absolute washboard... kinda had a nerdy face but his muscles were amazing. He slid out of his shorts and I got on my knees to suck his uncut fairly small cock, I was pleasantly surprised to watch it grow to about 7” shaped like a pop can with the head the same width of his very thick shaft.
He tasted sweaty and masculine and I grabbed his thick muscular thighs as I bobbed on his cock, making him grunt in satisfaction. We moved to the bed and I sucked his cock and licked his asshole till he almost came. I climbed on top of him tried to guide him into me before realizing I had my plug in. My pussy was so loose I had forgotten so I removed it and rode him in cowgurl while I ran my hands all over his rippling shoulders and amazing pecs. I had an unreal sissygasm while riding him and was quick to jump off and lick my sissy cummies from his chest before getting on my back and having him take me in missionary, feeling his Adonis body holding my legs back and driving into my like a jackhammer had my legs shaking my clit dipping uncontrollably. His massive frame was dripping sweat as he finally pumped his load inside me and collapsed on the bed next to me. I sucked his cock clean and he was rock hard again within a few minutes... he fucked me in spoon for a while before having me ride him again and pumping another load inside me before jumping in the shower.
After beefcake left my pussy was feeling pretty used... I douched and decided to leave my plug out for a while, no reply yet from the black gentleman so I decided to just watch hypno and checked in on him every hour or so. I was only able to keep myself from riding my dildo for a couple hours and after fucking a small load out of my clitty I was excited to see a reply from mr BBC. He only had an hour free so it was lucky I checked so often... I sent my address and he was there about 15 min later.
He was nearly as tall as me and in fairly good shape... little grey in the hair, maybe 45 or 50. He undressed without a word and after feeling me up and noticing my large plug he decided to get straight to fucking me. He had me lay back on the bed and pulled my to the edge holding my legs up... he removed my plug and slid his roughly 8” black cock inside my sissy pussy... my first true bbc. It was incredible, not my biggest cock but as a sissy the mental joy of being fucked by a BBC is something else entirely. His cock was decently thick but the best part was that he curved upward quite a bit and as he fucked me on my back he worked my p-spot so good my clit was just a non stop faucet. He rubbed his cock in the little puddle of cum dribbling out of me and used it as lube. We switched to doggy and he fucked me hard, like so hard my hotel bed came off the wall... we switched to the other bed and he fucked me again on my back till he pulled out and shot his load on my caged up clit. I did my best to scoop up his cum and swallow it all before cleaning his cock. He was still hard for a while and he fucked me in doggy for a little while before having to get back to his wife. I told him to save it and come back tomorrow for round two. I gave him my actual cell phone number and he entered it in his phone under Katie Work lol. Hopefully I see more of him.
It was now 6pm and I had sent my address and a few more pics to my gangbang crew, he’d responded saying all was a go and said to make sure I was ready for 8pm. I decided to wear just a body stocking with my blonde wig and a red Lycra top with a tiny red skirt... I pre tore my body stocking so my clit was dangling and my huge plug was clearly visible. I watched sissy porn until 7:45 then waited on the good bed until there was a knock at about 8:05... I opened the door and two decent looking 30 something East Indian guys introduced themselves and I let them in... they explained that they had another friend coming and he was now bringing a friend as well. I of course agreed to the addition and the were soon mostly undressed... I started with the guy I had been chatting with Sat he had a little more than 7” uncut cock with a thick head and a huge set of hairy balls, I sucked his cock as his friend Raj placed my hand on his thick rock hard cock, he was about 6.5” and shaped like a stubby beer bottle. I was fascinated and pulled away from Sat to suck and stroke Raj’s cock. His foreskin was loose and I pulled it back to lick and suck on his massive plump head. Sat pulled the plug from my pussy and fingered and fucked my ass as I sucked on Raj’s juicy cock... Sat began to work his fist into my ass as I heard another knock at the door. Sat answered the door and I looked up from Raj’s lap to see a tall thin man with a turban and a very well built very dark older guy with a large beard. Sat introduced me as whore Katie and the tall man was introduced as Rick while the older man was introduced as Mo. I returned to sucking Raj’s cock as the new arrivals got undressed... Sat was telling them about how stretched out my sissy pussy was and they all took delight in my little pink sissy clit all caged up. He worked his fist fairly easily into me after the stretching I took earlier... Raj allowed Rick to take his place and I was excited to see a nice thick semi hard cock in front of me. I sucked Ricks cock as Sat replaced his fist with his cock and pounded away on me, pulling out and having me push out my pussy while he slammed his cock in and out of me, Rick was soon a hard thick nine inches and was asking for his turn on my ass. Sat pulled out and Rick soon replaced him, Mo’s cock was still limp but hung very heavy and low, I could see his head pronounced through his foreskin. As Rick rhythmically fucked my ass pulling out every now end then so Sat could push his fist inside me, I sucked Mo’s big cock, as it grew the forskin pulled back and his huge dark purple cock head broke free, dripping with precum. I greedily sucked his cock for all I was worth as I grew to be at least 9” and very thick and veiny. Rick pulled out and Raj took a turn before Mo sat on the edge of the bed and asked me to ride him cowgirl. I easily took his huge cock and he was fucking me in quick deep strokes when Sat suggested I could take two cocks... I happily agreed and Mo pulled me down on his cock as Sat pushed himself in from behind. There wasn’t really much discomfort and after Sat applied a little more lube he and Mo were both fucking me with a fairly quick rhythm. I sissygasmed as they fucked away on me and Mo came after about 10 min of he and Sat double fucking my sissy pussy. After I cleaned Mo’s rapidly shrinking cock Sat went back to fisting my now cummy hole, I sucked on Ricks cock and Raj soon replaced Sats fists with his cock and pounded me in doggy until he blew his load inside me. I cleaned Raj’s cock and noticed Mo fully dressed waiting by the door. Rick now got behind me and seemingly in a hurry he pounded away aggressively until he dumped yet another load into my very well used cunt. I cleaned his cock and he quickly dressed as Sat pulled me down onto his cock as he sat on the edge of the bed. He fucked up into me while holding me still and made me squirt piss/cum from my clitty. He pounded me for a while after Mo and Rick left. Sat moved me into doggy before pounding a load into me and I sucked Raj rock hard again while Sat bred me so as Sat watched and played in his phone I rode Raj’s beer bottle thick cock before sucking another load out and swallowing it all like a good slut. My pussy was aching from all the abuse it had endured but that didn’t stop Sat from fisting my cummy swollen hole for another half hour before fucking one last load into me and putting in my now small feeling new large plug. I was totally used up and filled with cum, total sissy bliss.
As Sat and Raj dressed and left I lay on the bed in a daze, I managed to drink some water and smoke a joint before deleting my doublelist add and passing out from sheer exhaustion with my plug still in and my makeup smeared all over my face.
Another extremely successful day... 6 new cocks and one repeat cock... was stretched beyond belief though and my sissy cunt is definitely feeling the effects. May need to give my pussy a real break... then again
to be continued
I woke up a couple times in the night with painful sissy cramps in my chastity cage but managed to ride my large dildo till the annoyance passed. I was out of bed and into the shower by 9 the next morning... my brown daddy from the night before was coming at 10 so I quickly douched and shaved and got into my purple thigh highs and my tight purple t-shirt that says sissy on it in large pink letters, I wore a black wig and just had time to get my makeup mostly done when he was knocking at the door. I hadn’t had time to check my doublelist messages yet.
I quickly applied some lipstick and rinsed with scope before answering the door. He hurried into my room and seemed a little annoyed that I’d made him wait... I apologized and asked if I could make it up to him, he slipped out of his joggers and pointed his semi hard dark brown cock at me... I engulfed his cock with my wet mouth and gently stroked his shaft. He again became very vocal and called me his little whore and his cum slut, he moaned as he aggressively began throat fucking me... I gagged and coughed and even puked a tiny bit and it all just made him moan more loudly and grab the back of my head as he deep throat face fucked me. After a little while he pulled his cock free and told me to look in the mirror before he bred me... I stood and saw my make up destroyed and my shirt covered in saliva, I looked like a used up trashy whore and it made me swell in my cage. I fixed my wig and he led me onto the bed and onto my hands and knees in doggy with my legs together and my caged clit pulled back on display, I felt him press his cock against my now very open sissy pussy lips and push himself all the way in before resting with his big balls pressed against my smooth full sissy balls. He pulled almost all the way out and then slammed back in hard, doing this several times before settling into a slow deep rhythm... his balls slapping against my little locked up package with each thrust. He made sure I knew how pathetic I looked with his big brown cock fucking my well used sissy cunt and my little caged clit dribbling away. I was starting to feel like I was going to have a sissygasm when he began to fuck me much faster and grabbed my hips... pulling me onto him hard as he bred me deep. He pulled out and I quickly turned and cleaned his cock with my mouth, making sure to suck every last drop. I thanked him for his load and he quickly dressed and commented on how slutty I looked before leaving, I tried to fix my make up but it was beyond repair so I stripped it right off and then decided while I was not too slutted up to find a sex shop and get a larger plug.
I pulled on some panties to match my stockings and put on some loose fitting boy clothes before looking online and finding a suitable shop a 5 min drive away. It didn’t open for 30 min still though so I decided to check my doublelist messages and could not believe the deluge of replies. Big cities are the place to be for sissy cum dumps apparently lol. Sadly I had not heard back from the huge cock older guy I’d seen the night before and replies didn’t have any pics as I’d requested and there were several that just seemed too shady but one reply was from another East Indian guy asking if I would like to host he and his two friends, he’d supplied a pic with all three of them pointing they’re cocks at each other and I could just picture myself in the middle being a spoiled rotten sissy. None of them had a massive cock but they all put my little fag clit to shame and I had always wanted to be gangbanged so I messaged him back with a pic of me pulling my sissy pussy open in a spoon position and my caged clit poking out between my thighs and asked him to name a time. Then I headed out to the sex shop.
I arrived with still 10min before opening and waited in the parking lot... across from me was an elderly guy who was staring in my direction, I waited for the store to open and wanting to be alone in there I waited to see if he would go in before I finally decided to go. I made my way into the small shop and was surprised to find it very well equipped with larger toys and even a small selection of chastity cages. I asked the clerk where I would find plugs and the large older lady behind the counter kindly pointed them out, I looked over several and had decided on a 2.5” wide plug with a round base when I realized the old man from the parking lot was standing just behind me. I moved away slightly and he motioned towards the package in my hand and asked if I needed any help breaking it in... I blushed and stuttered a little embarrassed, I paused for a second before suggesting he follow me to my hotel and do just that. He agreed and I quickly went to the till and paid, he told me to wait in the parking lot and he came out soon as well carrying a large bag.
He followed me back to my hotel and brought the bag with him as he followed me up to my room, he was grabbing my ass all the way up the stairs and found my caged up clit as I we made our way through the door. He was not very happy I was caged and asked me to take it off but I hadn’t even brought the keys with me and I had no desire to be uncaged, he complained a little more but I slid out of my boy clothes and he was soon greedily eating my sissy pussy and fingering me. He reached into his bag and pulled out a large tapered black dildo that looked like it went from about 1.5” wide to around 3” wide. He pushed it in slowly at first but soon realized how open my pussy already was and was not gentle as he gave my pussy an unbelievable stretching with that huge toy... I moaned and at times cried as he used me until he was able to pull the toy loose and slide his whole fist in with ease, he punched fucked my pussy for a while before pulling his semi hard cock out and sliding it inside my now loose cunt. He never seemed to get hard but came a respectable load on my back before using his cum to lube my new plug and filling me up with it, it was luckily big enough to stay even after all that stretching and I lay there worn out for a while as he dressed and left, leaving the large toy he’d bought on the bedside table.
I checked my messages and saw that my gangbang crew wanted to come for 8:00 so I confirmed that and replied to a black guy who looked to have a nice big cock and a shorter bodybuilder guy that never sent a cock pic but looked so dominant I didn’t really care. Then I smoked a joint and put on my makeup while watching sissy hypno on my iPad. The bodybuilder guy got back to me right away and could head over ASAP so I sent him my address and he was there in about 45min.
He complimented me on my outfit and was surprisingly soft spoken and gentle for a guy of his stature, every muscle was incredibly well defined and his abs were absolute washboard... kinda had a nerdy face but his muscles were amazing. He slid out of his shorts and I got on my knees to suck his uncut fairly small cock, I was pleasantly surprised to watch it grow to about 7” shaped like a pop can with the head the same width of his very thick shaft.
He tasted sweaty and masculine and I grabbed his thick muscular thighs as I bobbed on his cock, making him grunt in satisfaction. We moved to the bed and I sucked his cock and licked his asshole till he almost came. I climbed on top of him tried to guide him into me before realizing I had my plug in. My pussy was so loose I had forgotten so I removed it and rode him in cowgurl while I ran my hands all over his rippling shoulders and amazing pecs. I had an unreal sissygasm while riding him and was quick to jump off and lick my sissy cummies from his chest before getting on my back and having him take me in missionary, feeling his Adonis body holding my legs back and driving into my like a jackhammer had my legs shaking my clit dipping uncontrollably. His massive frame was dripping sweat as he finally pumped his load inside me and collapsed on the bed next to me. I sucked his cock clean and he was rock hard again within a few minutes... he fucked me in spoon for a while before having me ride him again and pumping another load inside me before jumping in the shower.
After beefcake left my pussy was feeling pretty used... I douched and decided to leave my plug out for a while, no reply yet from the black gentleman so I decided to just watch hypno and checked in on him every hour or so. I was only able to keep myself from riding my dildo for a couple hours and after fucking a small load out of my clitty I was excited to see a reply from mr BBC. He only had an hour free so it was lucky I checked so often... I sent my address and he was there about 15 min later.
He was nearly as tall as me and in fairly good shape... little grey in the hair, maybe 45 or 50. He undressed without a word and after feeling me up and noticing my large plug he decided to get straight to fucking me. He had me lay back on the bed and pulled my to the edge holding my legs up... he removed my plug and slid his roughly 8” black cock inside my sissy pussy... my first true bbc. It was incredible, not my biggest cock but as a sissy the mental joy of being fucked by a BBC is something else entirely. His cock was decently thick but the best part was that he curved upward quite a bit and as he fucked me on my back he worked my p-spot so good my clit was just a non stop faucet. He rubbed his cock in the little puddle of cum dribbling out of me and used it as lube. We switched to doggy and he fucked me hard, like so hard my hotel bed came off the wall... we switched to the other bed and he fucked me again on my back till he pulled out and shot his load on my caged up clit. I did my best to scoop up his cum and swallow it all before cleaning his cock. He was still hard for a while and he fucked me in doggy for a little while before having to get back to his wife. I told him to save it and come back tomorrow for round two. I gave him my actual cell phone number and he entered it in his phone under Katie Work lol. Hopefully I see more of him.
It was now 6pm and I had sent my address and a few more pics to my gangbang crew, he’d responded saying all was a go and said to make sure I was ready for 8pm. I decided to wear just a body stocking with my blonde wig and a red Lycra top with a tiny red skirt... I pre tore my body stocking so my clit was dangling and my huge plug was clearly visible. I watched sissy porn until 7:45 then waited on the good bed until there was a knock at about 8:05... I opened the door and two decent looking 30 something East Indian guys introduced themselves and I let them in... they explained that they had another friend coming and he was now bringing a friend as well. I of course agreed to the addition and the were soon mostly undressed... I started with the guy I had been chatting with Sat he had a little more than 7” uncut cock with a thick head and a huge set of hairy balls, I sucked his cock as his friend Raj placed my hand on his thick rock hard cock, he was about 6.5” and shaped like a stubby beer bottle. I was fascinated and pulled away from Sat to suck and stroke Raj’s cock. His foreskin was loose and I pulled it back to lick and suck on his massive plump head. Sat pulled the plug from my pussy and fingered and fucked my ass as I sucked on Raj’s juicy cock... Sat began to work his fist into my ass as I heard another knock at the door. Sat answered the door and I looked up from Raj’s lap to see a tall thin man with a turban and a very well built very dark older guy with a large beard. Sat introduced me as whore Katie and the tall man was introduced as Rick while the older man was introduced as Mo. I returned to sucking Raj’s cock as the new arrivals got undressed... Sat was telling them about how stretched out my sissy pussy was and they all took delight in my little pink sissy clit all caged up. He worked his fist fairly easily into me after the stretching I took earlier... Raj allowed Rick to take his place and I was excited to see a nice thick semi hard cock in front of me. I sucked Ricks cock as Sat replaced his fist with his cock and pounded away on me, pulling out and having me push out my pussy while he slammed his cock in and out of me, Rick was soon a hard thick nine inches and was asking for his turn on my ass. Sat pulled out and Rick soon replaced him, Mo’s cock was still limp but hung very heavy and low, I could see his head pronounced through his foreskin. As Rick rhythmically fucked my ass pulling out every now end then so Sat could push his fist inside me, I sucked Mo’s big cock, as it grew the forskin pulled back and his huge dark purple cock head broke free, dripping with precum. I greedily sucked his cock for all I was worth as I grew to be at least 9” and very thick and veiny. Rick pulled out and Raj took a turn before Mo sat on the edge of the bed and asked me to ride him cowgirl. I easily took his huge cock and he was fucking me in quick deep strokes when Sat suggested I could take two cocks... I happily agreed and Mo pulled me down on his cock as Sat pushed himself in from behind. There wasn’t really much discomfort and after Sat applied a little more lube he and Mo were both fucking me with a fairly quick rhythm. I sissygasmed as they fucked away on me and Mo came after about 10 min of he and Sat double fucking my sissy pussy. After I cleaned Mo’s rapidly shrinking cock Sat went back to fisting my now cummy hole, I sucked on Ricks cock and Raj soon replaced Sats fists with his cock and pounded me in doggy until he blew his load inside me. I cleaned Raj’s cock and noticed Mo fully dressed waiting by the door. Rick now got behind me and seemingly in a hurry he pounded away aggressively until he dumped yet another load into my very well used cunt. I cleaned his cock and he quickly dressed as Sat pulled me down onto his cock as he sat on the edge of the bed. He fucked up into me while holding me still and made me squirt piss/cum from my clitty. He pounded me for a while after Mo and Rick left. Sat moved me into doggy before pounding a load into me and I sucked Raj rock hard again while Sat bred me so as Sat watched and played in his phone I rode Raj’s beer bottle thick cock before sucking another load out and swallowing it all like a good slut. My pussy was aching from all the abuse it had endured but that didn’t stop Sat from fisting my cummy swollen hole for another half hour before fucking one last load into me and putting in my now small feeling new large plug. I was totally used up and filled with cum, total sissy bliss.
As Sat and Raj dressed and left I lay on the bed in a daze, I managed to drink some water and smoke a joint before deleting my doublelist add and passing out from sheer exhaustion with my plug still in and my makeup smeared all over my face.
Another extremely successful day... 6 new cocks and one repeat cock... was stretched beyond belief though and my sissy cunt is definitely feeling the effects. May need to give my pussy a real break... then again
to be continued
5年前
