Crossdressersa ed and Turned Out Ch 02
- 3 years ago
- 45
- 0
Cross Dressers First Time free porn video
I was in my mid 40's and divorced and living a great life. I ran my own successful from home and lived in a large house in it's own grounds at least 5 miles from my nearest neighbour.
Whilst I was single I had an active sex life having been lucky enough to know 3 ladies who were unattached and had no need for a long term relationships but were happy to meet up for sex or go away for a break all no strings attached. They all knew of each other and I was aware they saw other men or ladies if they wished.
Debi was 50 a successful lawyer and very dirty. Helen was 60 a retired business woman sexy and great in bed and Sarah was my age a nurse who loved sex and could use me all night.
What I kept quiet and has since I was young was that I cross dressed. I now had a locked closet full of ladies, clothes, lingerie, shoes and wigs and make up. I would indulge myself and dress as my alter ego Paula at least once a month and enjoy time being a sexy lady. The dressing relaxed me and I had never really seen myself as gay or bi it was just my bit of fun.
I had only ever been seen twice in ladies clothes. Once, shortly after my divorce, when I visited a dressing service as I knew I would be dressing more often and the other time I visited an escort and wore panties and stockings when we had sex.
He dressing service helped me look quite passable. I was only 5 feet 7 and slim and fairly hair free. I now kept myself completely waxed which I explained was due to the fact I did a lot of cycling (no lie).
I had found myself drawn more to cross dresser porn and often fantasised about sex with men but apart from dressing cam sessions I had never had a sexual encounter with a man and saw myself as curious only.
It was a December day and I had decided to be Paula for the day. I had put on white lace lingerie including lacy boy shorts. I had put on suspenders and cream stockings with black seams. I slipped on a short little black dress which showed off my slim legs and some black stilettos. I applied some discreet make up and my block bob wig. I was not worried about surprise visitors as the only way on to my property was through security gates and I has a sophisticated alarm system which would warn of intruders.
I did some work during the day enjoying the thought of clients and my broker talking to me unaware that I was dressed up as (even though I say so myself) a sexy milf. By the afternoon I had done my work and logged onto my computer and started looking at some of my favourite porn sites and enjoyed the films of some hot cross dressers I stroked myself through my panties but held off cumming as I planned a long night of porn and cum as I was not expecting to see anyone that evening. Pre-cum oozed through the lace panties and I decided to stop for a while and get a drink and watch the news. Due to my location I rarely closed the curtains and I could see outside that snow was falling so I decided to pop out and get some logs for my wood burner. I slipped of my shoes and put on my trainers but otherwise I went out as Paula. I got some wood from my store I went back into the house. I slipped off my trainers and padded in my stocking feet to my wood burner and began to put wood in the stove. As I closed the door a hand was clasped over my face. I went rigid with shock.
“ Surprise!” rasped a husky voice. “I bet you thought all that security was fool proof didn’t you you sissy fag?”
“Well it isn't. I've been watching you online and through you stupidly big windows for weeks, Nice of you to give me those shows,”
“I'm going to take my hand away. No point in screaming no one will hear.” He laughed as he turned me around.
I saw a man in his 30's about5 feet 11. Muscular, hairy and dressed in a blue overall with the logo of my alarm systems installers on them/
“I haven't any cash in the house but take any valuables you want,” I whispered.
“I'm not here to rob you I'm here to have you,” he leered.
I gasped and tried to break free nut he was far stronger than me.
“You'll go to prison,” I said.
“Not when people see the videos I have of you dressed up and camming for men asking them to fuck you.. Your whole house is wired and some of your cam games were for me Tommyboy1245.”
My head was reeling I couldn't believe this was happening to me. I thought I had been so discreet. Scandal would ruin me.
He moved over to my sofa and undid his overalls revealing a very hairy naked hard muscular body with a cock already hardening. It wasn't huge but for the first hard cock I'd seen in real life it was scary.
“On your knees Paula I need a warm mouth around me,” His hands forced me down and he sat on my sofa legs spread. He pulled me towards him and my head moved towards his glistening circumcised cock.
“Start sucking baby or your world gets blown apart,”
I slowly lowered my mouth and put my lips on his cock. I tasted salty muskiness and began to take more into my mouth, I wanted to gag but somehow kept it in, I remembered the films I'd seen and began wanking and sucking the cock,
“Ohhhhhhhhhhhh yeah baby I have wanted this for weeks. I knew you were a sissy cock sucking bitch” he moaned.
Despite myself my cock was rigid in my lace panties. After a few minutes he groaned and I felt him go rigid and a gush of hot spunk hit my mouth. I tried to pull away but he held me tight and made me swallow. The salty seed slid down making me feel sick but smutty and horny. I had often had this fantasy the reality was scarier and more exciting.
“Nice work Paula you suck cock like a pro. Now lets have scotch and you the you can take that dress off.”
I fixed his drink and then slowly took off my dress revealing my sexy lingerie and hard cock.
“Your a big gurl for a sissy. “Tommy said looking at my 7 inch cock, It's size surprised all my partners.
“Come over here and sit on the sofa.” he said and patted the seat. As I walked over he removed all of his clothing and sat down next to me completely naked, He took me in his arms and pulled me to his mouth and began to kiss me his tongue sliding into my mouth. I had never kissed a man and found myself responding to him and began using my tongue. His rough hands ran over my body and I found my hand on his hard again cock. I stroked him and he moaned and kissed me harder. His hand slid into my panties and a finger found my ass and slid inside me. He worked my ass and I found I was moving myself on his now 3 fingers, He pulled away and lay pushed me down on to my back and he reached into his overalls and brought out a tube of lube. He pulled my panties aside and began putting lots of lube in my ass.
“Time to lose your cherry Paula.”
He took his time entering me until I could feel him fully in me, At first it was painful but the more he worked me the better it felt. After 20 minutes my legs were around his back as he fucked me. Eventually he stiffened and shouted out my name as a gush of cum filled my ass. He collapsed on me and we kissed again. I could not believe I had enjoyed it so much.
The rest of the evening was spent with him using me in every position. He must have cum 5 times and I had cum in my own panties.
We feel asleep on the rug in my lounge with Tommy caressing my cock.
I heard a bleep and woke with a start. I was covered in a blanket and alone, I was wearing cum covered lingerie and the room smelt of sex. I had no idea where Tommy was,
In heard the bleep again and looked at my computer. I saw Debi's smiling face.
“Hi darling didn't I tell you a £1000 spent at Fantasies Cum True was worth it. Thanks for telling me about Paula and putting the cam on. I frigged my cunt so hard last night watching your deflowering. I will be over tonight to meet Paula” She stood up showing her fit naked body wand the 8 inch strap on dildo she was wearing.
I smiled “looking forward to it sexy.”
“Maybe we could book them for some joint fun,” she said.
“That would be great "I sighed,
I drifter off to sleep again dreaming of last night.
Whilst I was single I had an active sex life having been lucky enough to know 3 ladies who were unattached and had no need for a long term relationships but were happy to meet up for sex or go away for a break all no strings attached. They all knew of each other and I was aware they saw other men or ladies if they wished.
Debi was 50 a successful lawyer and very dirty. Helen was 60 a retired business woman sexy and great in bed and Sarah was my age a nurse who loved sex and could use me all night.
What I kept quiet and has since I was young was that I cross dressed. I now had a locked closet full of ladies, clothes, lingerie, shoes and wigs and make up. I would indulge myself and dress as my alter ego Paula at least once a month and enjoy time being a sexy lady. The dressing relaxed me and I had never really seen myself as gay or bi it was just my bit of fun.
I had only ever been seen twice in ladies clothes. Once, shortly after my divorce, when I visited a dressing service as I knew I would be dressing more often and the other time I visited an escort and wore panties and stockings when we had sex.
He dressing service helped me look quite passable. I was only 5 feet 7 and slim and fairly hair free. I now kept myself completely waxed which I explained was due to the fact I did a lot of cycling (no lie).
I had found myself drawn more to cross dresser porn and often fantasised about sex with men but apart from dressing cam sessions I had never had a sexual encounter with a man and saw myself as curious only.
It was a December day and I had decided to be Paula for the day. I had put on white lace lingerie including lacy boy shorts. I had put on suspenders and cream stockings with black seams. I slipped on a short little black dress which showed off my slim legs and some black stilettos. I applied some discreet make up and my block bob wig. I was not worried about surprise visitors as the only way on to my property was through security gates and I has a sophisticated alarm system which would warn of intruders.
I did some work during the day enjoying the thought of clients and my broker talking to me unaware that I was dressed up as (even though I say so myself) a sexy milf. By the afternoon I had done my work and logged onto my computer and started looking at some of my favourite porn sites and enjoyed the films of some hot cross dressers I stroked myself through my panties but held off cumming as I planned a long night of porn and cum as I was not expecting to see anyone that evening. Pre-cum oozed through the lace panties and I decided to stop for a while and get a drink and watch the news. Due to my location I rarely closed the curtains and I could see outside that snow was falling so I decided to pop out and get some logs for my wood burner. I slipped of my shoes and put on my trainers but otherwise I went out as Paula. I got some wood from my store I went back into the house. I slipped off my trainers and padded in my stocking feet to my wood burner and began to put wood in the stove. As I closed the door a hand was clasped over my face. I went rigid with shock.
“ Surprise!” rasped a husky voice. “I bet you thought all that security was fool proof didn’t you you sissy fag?”
“Well it isn't. I've been watching you online and through you stupidly big windows for weeks, Nice of you to give me those shows,”
“I'm going to take my hand away. No point in screaming no one will hear.” He laughed as he turned me around.
I saw a man in his 30's about5 feet 11. Muscular, hairy and dressed in a blue overall with the logo of my alarm systems installers on them/
“I haven't any cash in the house but take any valuables you want,” I whispered.
“I'm not here to rob you I'm here to have you,” he leered.
I gasped and tried to break free nut he was far stronger than me.
“You'll go to prison,” I said.
“Not when people see the videos I have of you dressed up and camming for men asking them to fuck you.. Your whole house is wired and some of your cam games were for me Tommyboy1245.”
My head was reeling I couldn't believe this was happening to me. I thought I had been so discreet. Scandal would ruin me.
He moved over to my sofa and undid his overalls revealing a very hairy naked hard muscular body with a cock already hardening. It wasn't huge but for the first hard cock I'd seen in real life it was scary.
“On your knees Paula I need a warm mouth around me,” His hands forced me down and he sat on my sofa legs spread. He pulled me towards him and my head moved towards his glistening circumcised cock.
“Start sucking baby or your world gets blown apart,”
I slowly lowered my mouth and put my lips on his cock. I tasted salty muskiness and began to take more into my mouth, I wanted to gag but somehow kept it in, I remembered the films I'd seen and began wanking and sucking the cock,
“Ohhhhhhhhhhhh yeah baby I have wanted this for weeks. I knew you were a sissy cock sucking bitch” he moaned.
Despite myself my cock was rigid in my lace panties. After a few minutes he groaned and I felt him go rigid and a gush of hot spunk hit my mouth. I tried to pull away but he held me tight and made me swallow. The salty seed slid down making me feel sick but smutty and horny. I had often had this fantasy the reality was scarier and more exciting.
“Nice work Paula you suck cock like a pro. Now lets have scotch and you the you can take that dress off.”
I fixed his drink and then slowly took off my dress revealing my sexy lingerie and hard cock.
“Your a big gurl for a sissy. “Tommy said looking at my 7 inch cock, It's size surprised all my partners.
“Come over here and sit on the sofa.” he said and patted the seat. As I walked over he removed all of his clothing and sat down next to me completely naked, He took me in his arms and pulled me to his mouth and began to kiss me his tongue sliding into my mouth. I had never kissed a man and found myself responding to him and began using my tongue. His rough hands ran over my body and I found my hand on his hard again cock. I stroked him and he moaned and kissed me harder. His hand slid into my panties and a finger found my ass and slid inside me. He worked my ass and I found I was moving myself on his now 3 fingers, He pulled away and lay pushed me down on to my back and he reached into his overalls and brought out a tube of lube. He pulled my panties aside and began putting lots of lube in my ass.
“Time to lose your cherry Paula.”
He took his time entering me until I could feel him fully in me, At first it was painful but the more he worked me the better it felt. After 20 minutes my legs were around his back as he fucked me. Eventually he stiffened and shouted out my name as a gush of cum filled my ass. He collapsed on me and we kissed again. I could not believe I had enjoyed it so much.
The rest of the evening was spent with him using me in every position. He must have cum 5 times and I had cum in my own panties.
We feel asleep on the rug in my lounge with Tommy caressing my cock.
I heard a bleep and woke with a start. I was covered in a blanket and alone, I was wearing cum covered lingerie and the room smelt of sex. I had no idea where Tommy was,
In heard the bleep again and looked at my computer. I saw Debi's smiling face.
“Hi darling didn't I tell you a £1000 spent at Fantasies Cum True was worth it. Thanks for telling me about Paula and putting the cam on. I frigged my cunt so hard last night watching your deflowering. I will be over tonight to meet Paula” She stood up showing her fit naked body wand the 8 inch strap on dildo she was wearing.
I smiled “looking forward to it sexy.”
“Maybe we could book them for some joint fun,” she said.
“That would be great "I sighed,
I drifter off to sleep again dreaming of last night.
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