Gary s Dressup Sissy
- 4 years ago
- 48
- 0
Moms Friend 2 - Dressup Slut free porn video
so I had been visiting Linda for about 8 weeks. Every oportunity I got. My mom was none the wiser. I'd invented a girlfriend that I was seeing. Linda had backed up this story by telling mom that she had seen me with her.
little did she know I was visiting her best friend to dress up as a whore every chance i got.
Linda had had to lay down some ground rules. I had to dress in the outfit she had picked out for me as soon as I entered her house. She would watch me dress.
Linda insisted I wear suspenders and stockings. I was fine with this as i just loved the look of my cock, framed by lace topped stockings and suspenders.
I had to immediately put on my chastity device. This was made of leather with chrome rings. The rings were tight around my balls and then a leather sheeth covered my cock, the sheeth was fastened with leather laces, to ensure a tight fit, and then secured with 2 tiny silver padlocks, finally, my cock was tucked back to my balls and secured with a 3rd lock. not only did this device prevent me cumming. it was uncomfortable for me to even get hard.
Linda had insisted on the device following my seeming innability to not cum the second she touched my cock. she said I was suffering from something called premature ejaculation.
Linda always referred to me as "princess" once I was dressed.
Once I was dressed, Linda would often tease me about being such a sissy, and threaten to never allow me to cum again. I had promised that I would not jerk off until she allowed me. it had been 3 weeks now, and I had been good to my word, although I had had several wet dreams. I'd explained this to Linda. I was allowed these, as long as I informed Linda Immediately.
Following the teasing ritual, I would eat Linda's pussy. She had explained that she loved to have her pussy eaten. i would eat her until she had several orgasms. each seemingly stronger than the next. I would then be freed from my chastity, undress, shower whilst Linda watched and then be sent home.
Whilst dressed as princess, Linda had introduced me to her neighbours. This had been a mortifyingly embarrassing experience, until I had realised they were 2 gay guys, and were actually very understanding and realy nice guys named Andy and Mark.
One Friday morning, I was sat in class, looking forward to that evenings visit to linda, when I felt my phone vibrate in my pocket. The phone had been supplied to me by Linda, and she was the only person who had this number. Secretly i sneeked a look at the phone. the message read " be here straight from school, we have been invited out this evening, you'll need extra time to get ready"
My heart pounded in my chest, where was she planning on taking "princess"
I made my excuses to mom, and was a Linda's for about 4.00pm
I showered and made sure i was smooth all over. This was an easy task as I was not a hairy boy at all. I left the bathroom and went to Linda's spare room where she was waiting. The room had become "princess' drsssing room. and contained a small cot bed for when i satayed over. a wardrobe and chest of drawers containing Princess' clothes and a full length cheval mirror.
Quickly Linda fastened me into my chastity device and told me to dress.
Linda had laid out my outfit as usual. I bagan to dress in front of her. black lace suspender belt, opaque black lace topped stockings. the stocking were hold ups, but I was still to wear the suspenders. Black lace panties. Linda had taught me to always wear my panties over my suspenders.
Next was a small A cup black lace bra, into which Linda slipped some small silicon breast forms. these were held in place by a glue to my chest, and linda quickly hid the joins with makeup. She grinned and winked at me.
Next I slid a short red velvet dress over my head. too short, although it hid my cock and suspenders, my lace topped stocking were clearly visible below the hem of the dress. I looked at Linda. "perfect" she said.
I gulped......she was taking me out dressed like this?
The for my shoes, they were black with 6" heels and a 2" platform. I had been practicing walking in these for weeks. I had mastered walking and even a sexy wiggle, but they still almost crippled me.
Next Linda led me to her room. All chifon and chintz. she sat me down at her dressing table. and straightened my shoulder length blonde hair. usually my hair just looked a little unkempt, but when straighted, it was a perfect girly bob. Linda loved this. Finally she applied my makeup. finished of with a dark red, almost black lipstick. she led me back to my room, for me to admire her work in the mirror. I looked amazing, other than the small bulge where my chained cock sat in the front of the red dress, you'd never guess I was a boy.
Linda poured me a large glass of wine. and explained we were going out to a club that Andy and mark had reccomended. They would be calling for us at 8. which left and hour and a half for me to eat her pussy. As usual, I did as I was told.
The bell rang at 8.00 and Linda quickly re-applied my lipstick.
Andy was driving, the club was in town, about an hours drive.I sat in the back of Andy's car with Linda. Her hand resting on my stocking clad leg.
Mark seemed to know the doormen at the club, he whispered to one, who looked me up and down. he smiled and waved us in. clearly annoying the queue of patiently waiting customers. The club was small, and already quite full. It was my first club, and clearly a gay bar. most of the customers were guys, several women, who I assumed to be lesbian and a handful of transvestites. all of whom were already in the embrace of guys, none of whom looked anywhere near as hot as me.
after another large glass of wine, we descended to the dance floor. dancing in these shoes wasn't easy, but I was gathering a small audience.
Soon a large black guy approached. He was the doorman from earlier.
"wanna dance" he asked
"sure" I said
Linda and my friends backed away slightly, allowing us to dance together. I turned to face him and his hands were immediately on my bum. He pulled me to him, I could feel his semi erect cock against my belly. he stood around 6" taller than me (a foot if I wasn't in these heels)
I looked over at Linda. She was smiling approvingly. She had obviously planned this. I was petrified and yet unbelievably excited.
we danced for maybe 30 minutes. Each time he pulled me to him, he seemed more excited.
Finally, he leant in and shouted over the music into my ear.
"do you and your friends wanna come in the members area"
Linda had leaned in to listen, and she answered yes on our behalf. My suiter grabbed my hand and led me from the dance floor. The whole clubs eyes seemed to be on us and we climed a set of metal stairs. My short dress rode up even higher, revealing suspender straps and a glimps of bare thigh as I climbed the stairs.
At the top he unlocked the door and i entered a blackened room. the lights pinged into life.
The room was about half the size of the club below. There was a pool table, leather sofas and a bar in the corner.
We all entered and the door was locked behind us. The music from the club bacame a dull thudding noise.
"so princess, my name is Mike. Linda here tells me you're all going to put on a show for me tonight"
I looked over at Linda.....
"dont worry baby" she said "we're going to have fun"
Mike flicked another switch, and a spotlight shone on the far wall. We all walked over to it, Mike holding my hand a little tighter now. The wall was laid out like a display in a sex toy shop....covered in dildos, anal beads, tubes of lube....."oh wow" i muttered.
Linda raced to it Like a k** in a candy shop, and reached down a large purple glittery double ended dildo...."I've always wanted to try these" she squealed.
I felt Mikes hand and my back, undoing the zip to my dress. he slipped it of my shoulders and it dropped to the floor. I stepped out of it. standing before him in only my lingerie and heels.
Andy and Mark moved away to the pool table, kissing and undressing as they went.
Linda held my hand and led me to the leather settee area. Mike followed, a tube of lube in hand. Linda sat sideways on the first sofa, and pulled me down onto the seat before her. She kissed me on the lips and reassured me
"don't worry princess....I won't let anything bad happen to you ok?"
I nodded nervously.
Linda slipped out of her dress, to reveal Black lingerie, and stockings all similar to mine. She lay back and Mike took my shoulders and lay me back also.
We lay at oposite ends of the settee, like sardines in a tin. Our stocking clad legs entwined, the feel of which always delighted me. I closed my eyes as Mike removed my panties and playfully squeezed my cock through its leather harness.
He lubed us. first my ass and then Linda's pussy. I heard linda moaning in delight, obviously, gleefully taking the first end of the dildo. I felt its head at my boy pussy......so smooth and slippery and hard....Mike pushed harder and harder until I felt it parting me. once it had done so it slipped deep into me.....I gasped, first with pain....but then as it went deeper it felt so good.
Linda was writhing now....The more she wriggled the deeper the dildo went into me. deeper and deeper. finally our boddies met, between us we'd taken the whole of the phallus a good 18 inches. It felt as though I had taken the larger share, I could almost feel it tip pushing at the inside of my belly
Mike clearly liked what he was watching. as when I opened my eyes he was naked. and his cock was rock hard. He was jerking himself off as he watched. His angry cock glistened with pre-cum.
I licked my lips....."Mike" I said "Let me suck that for you"
I heard Linda Gasp and then giggle
"Pricess!....You dirty little cock whore" she said "well Mike...don't keep a girl waiting....stuff her mouth with that hard cock"
Andy and Mark broke off from there own little liason, and wondered over to our couch to watch the scene. They were both naked and erect.
As Mike moved around to the head of the settee....I looked at Andy and Mark...Mark moved to the other end of the sofa and lowered his cock into Linda's mouth....Mike's cock was at my face. Andy had something in his hand. I realised it was his cell phone. he was filming me.
I opened my mouth and Mike's hot cock was inside me....the taste of his precum was amazing to me.....god I wanted his cum too. I worked on the tip of his cock with my lips and tongue as he jerked frantically. Linda was sucking like her life depended on it too...as she did so, she was driving the double ender deeper into me. I felt Andy take my hand and move it to his cock. I grasped it and started jerking him too. seconds later I felt his cock twitching in my hand, I opened my eyes just in time to see his hot sperm spray over me, over my belly and my lingerie.
At the sight of this Mike cock began to spasm. I felt it ease a load of cum from its tip into my mouth, before his main orgasm struck. he stopped jerking and his cum gushed into my mouth....exploding out onto my chin and my cheek. He pulled it from me and sprayed shot after shot over my face and tits. finally putting it back to my lips for me to clean him.
I looked up at Linda....she too had cum all over her. She was beaming at me. Clearly loving the sight of me saturated in cum.
she reached a small chain necklace from around her neck on it hung a key....I recognised it as the key to my cocks cage.
"you've been a good girl Princess" she said "I think you've earned your own orgasm"
"Oh thank you I replied"
"but you know where I want you to cum now don't you princess?"
"No Linda?" I responded.
"oh Princess....now you've got the taste for cum....it would be such a shame to waste your own wouldn't it my little precious"
"Yes Linda" I replied
Fuck.....what the hell had I become?
little did she know I was visiting her best friend to dress up as a whore every chance i got.
Linda had had to lay down some ground rules. I had to dress in the outfit she had picked out for me as soon as I entered her house. She would watch me dress.
Linda insisted I wear suspenders and stockings. I was fine with this as i just loved the look of my cock, framed by lace topped stockings and suspenders.
I had to immediately put on my chastity device. This was made of leather with chrome rings. The rings were tight around my balls and then a leather sheeth covered my cock, the sheeth was fastened with leather laces, to ensure a tight fit, and then secured with 2 tiny silver padlocks, finally, my cock was tucked back to my balls and secured with a 3rd lock. not only did this device prevent me cumming. it was uncomfortable for me to even get hard.
Linda had insisted on the device following my seeming innability to not cum the second she touched my cock. she said I was suffering from something called premature ejaculation.
Linda always referred to me as "princess" once I was dressed.
Once I was dressed, Linda would often tease me about being such a sissy, and threaten to never allow me to cum again. I had promised that I would not jerk off until she allowed me. it had been 3 weeks now, and I had been good to my word, although I had had several wet dreams. I'd explained this to Linda. I was allowed these, as long as I informed Linda Immediately.
Following the teasing ritual, I would eat Linda's pussy. She had explained that she loved to have her pussy eaten. i would eat her until she had several orgasms. each seemingly stronger than the next. I would then be freed from my chastity, undress, shower whilst Linda watched and then be sent home.
Whilst dressed as princess, Linda had introduced me to her neighbours. This had been a mortifyingly embarrassing experience, until I had realised they were 2 gay guys, and were actually very understanding and realy nice guys named Andy and Mark.
One Friday morning, I was sat in class, looking forward to that evenings visit to linda, when I felt my phone vibrate in my pocket. The phone had been supplied to me by Linda, and she was the only person who had this number. Secretly i sneeked a look at the phone. the message read " be here straight from school, we have been invited out this evening, you'll need extra time to get ready"
My heart pounded in my chest, where was she planning on taking "princess"
I made my excuses to mom, and was a Linda's for about 4.00pm
I showered and made sure i was smooth all over. This was an easy task as I was not a hairy boy at all. I left the bathroom and went to Linda's spare room where she was waiting. The room had become "princess' drsssing room. and contained a small cot bed for when i satayed over. a wardrobe and chest of drawers containing Princess' clothes and a full length cheval mirror.
Quickly Linda fastened me into my chastity device and told me to dress.
Linda had laid out my outfit as usual. I bagan to dress in front of her. black lace suspender belt, opaque black lace topped stockings. the stocking were hold ups, but I was still to wear the suspenders. Black lace panties. Linda had taught me to always wear my panties over my suspenders.
Next was a small A cup black lace bra, into which Linda slipped some small silicon breast forms. these were held in place by a glue to my chest, and linda quickly hid the joins with makeup. She grinned and winked at me.
Next I slid a short red velvet dress over my head. too short, although it hid my cock and suspenders, my lace topped stocking were clearly visible below the hem of the dress. I looked at Linda. "perfect" she said.
I gulped......she was taking me out dressed like this?
The for my shoes, they were black with 6" heels and a 2" platform. I had been practicing walking in these for weeks. I had mastered walking and even a sexy wiggle, but they still almost crippled me.
Next Linda led me to her room. All chifon and chintz. she sat me down at her dressing table. and straightened my shoulder length blonde hair. usually my hair just looked a little unkempt, but when straighted, it was a perfect girly bob. Linda loved this. Finally she applied my makeup. finished of with a dark red, almost black lipstick. she led me back to my room, for me to admire her work in the mirror. I looked amazing, other than the small bulge where my chained cock sat in the front of the red dress, you'd never guess I was a boy.
Linda poured me a large glass of wine. and explained we were going out to a club that Andy and mark had reccomended. They would be calling for us at 8. which left and hour and a half for me to eat her pussy. As usual, I did as I was told.
The bell rang at 8.00 and Linda quickly re-applied my lipstick.
Andy was driving, the club was in town, about an hours drive.I sat in the back of Andy's car with Linda. Her hand resting on my stocking clad leg.
Mark seemed to know the doormen at the club, he whispered to one, who looked me up and down. he smiled and waved us in. clearly annoying the queue of patiently waiting customers. The club was small, and already quite full. It was my first club, and clearly a gay bar. most of the customers were guys, several women, who I assumed to be lesbian and a handful of transvestites. all of whom were already in the embrace of guys, none of whom looked anywhere near as hot as me.
after another large glass of wine, we descended to the dance floor. dancing in these shoes wasn't easy, but I was gathering a small audience.
Soon a large black guy approached. He was the doorman from earlier.
"wanna dance" he asked
"sure" I said
Linda and my friends backed away slightly, allowing us to dance together. I turned to face him and his hands were immediately on my bum. He pulled me to him, I could feel his semi erect cock against my belly. he stood around 6" taller than me (a foot if I wasn't in these heels)
I looked over at Linda. She was smiling approvingly. She had obviously planned this. I was petrified and yet unbelievably excited.
we danced for maybe 30 minutes. Each time he pulled me to him, he seemed more excited.
Finally, he leant in and shouted over the music into my ear.
"do you and your friends wanna come in the members area"
Linda had leaned in to listen, and she answered yes on our behalf. My suiter grabbed my hand and led me from the dance floor. The whole clubs eyes seemed to be on us and we climed a set of metal stairs. My short dress rode up even higher, revealing suspender straps and a glimps of bare thigh as I climbed the stairs.
At the top he unlocked the door and i entered a blackened room. the lights pinged into life.
The room was about half the size of the club below. There was a pool table, leather sofas and a bar in the corner.
We all entered and the door was locked behind us. The music from the club bacame a dull thudding noise.
"so princess, my name is Mike. Linda here tells me you're all going to put on a show for me tonight"
I looked over at Linda.....
"dont worry baby" she said "we're going to have fun"
Mike flicked another switch, and a spotlight shone on the far wall. We all walked over to it, Mike holding my hand a little tighter now. The wall was laid out like a display in a sex toy shop....covered in dildos, anal beads, tubes of lube....."oh wow" i muttered.
Linda raced to it Like a k** in a candy shop, and reached down a large purple glittery double ended dildo...."I've always wanted to try these" she squealed.
I felt Mikes hand and my back, undoing the zip to my dress. he slipped it of my shoulders and it dropped to the floor. I stepped out of it. standing before him in only my lingerie and heels.
Andy and Mark moved away to the pool table, kissing and undressing as they went.
Linda held my hand and led me to the leather settee area. Mike followed, a tube of lube in hand. Linda sat sideways on the first sofa, and pulled me down onto the seat before her. She kissed me on the lips and reassured me
"don't worry princess....I won't let anything bad happen to you ok?"
I nodded nervously.
Linda slipped out of her dress, to reveal Black lingerie, and stockings all similar to mine. She lay back and Mike took my shoulders and lay me back also.
We lay at oposite ends of the settee, like sardines in a tin. Our stocking clad legs entwined, the feel of which always delighted me. I closed my eyes as Mike removed my panties and playfully squeezed my cock through its leather harness.
He lubed us. first my ass and then Linda's pussy. I heard linda moaning in delight, obviously, gleefully taking the first end of the dildo. I felt its head at my boy pussy......so smooth and slippery and hard....Mike pushed harder and harder until I felt it parting me. once it had done so it slipped deep into me.....I gasped, first with pain....but then as it went deeper it felt so good.
Linda was writhing now....The more she wriggled the deeper the dildo went into me. deeper and deeper. finally our boddies met, between us we'd taken the whole of the phallus a good 18 inches. It felt as though I had taken the larger share, I could almost feel it tip pushing at the inside of my belly
Mike clearly liked what he was watching. as when I opened my eyes he was naked. and his cock was rock hard. He was jerking himself off as he watched. His angry cock glistened with pre-cum.
I licked my lips....."Mike" I said "Let me suck that for you"
I heard Linda Gasp and then giggle
"Pricess!....You dirty little cock whore" she said "well Mike...don't keep a girl waiting....stuff her mouth with that hard cock"
Andy and Mark broke off from there own little liason, and wondered over to our couch to watch the scene. They were both naked and erect.
As Mike moved around to the head of the settee....I looked at Andy and Mark...Mark moved to the other end of the sofa and lowered his cock into Linda's mouth....Mike's cock was at my face. Andy had something in his hand. I realised it was his cell phone. he was filming me.
I opened my mouth and Mike's hot cock was inside me....the taste of his precum was amazing to me.....god I wanted his cum too. I worked on the tip of his cock with my lips and tongue as he jerked frantically. Linda was sucking like her life depended on it too...as she did so, she was driving the double ender deeper into me. I felt Andy take my hand and move it to his cock. I grasped it and started jerking him too. seconds later I felt his cock twitching in my hand, I opened my eyes just in time to see his hot sperm spray over me, over my belly and my lingerie.
At the sight of this Mike cock began to spasm. I felt it ease a load of cum from its tip into my mouth, before his main orgasm struck. he stopped jerking and his cum gushed into my mouth....exploding out onto my chin and my cheek. He pulled it from me and sprayed shot after shot over my face and tits. finally putting it back to my lips for me to clean him.
I looked up at Linda....she too had cum all over her. She was beaming at me. Clearly loving the sight of me saturated in cum.
she reached a small chain necklace from around her neck on it hung a key....I recognised it as the key to my cocks cage.
"you've been a good girl Princess" she said "I think you've earned your own orgasm"
"Oh thank you I replied"
"but you know where I want you to cum now don't you princess?"
"No Linda?" I responded.
"oh Princess....now you've got the taste for cum....it would be such a shame to waste your own wouldn't it my little precious"
"Yes Linda" I replied
Fuck.....what the hell had I become?
Miracle
- 05.06.2021
- 20
- 0
