UpskirtTimes
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One evening I was online when someone wanted to start a chat with me. It was a bi guy who enjoyed cross dressing and having viewed his online profile I said “Hi” and we got to talking.
He was married guy named Mike and he had a very understanding wife who allowed him to meet men and allow him to explore his feminine side by dressing up. His wife did not participate with him and none of his explorations happened at home.
During our chat he explained he’d just bought a pair of long, nearly thigh high, boots and he longed to be fucked whilst wearing them. He was off that week and wondered if I wanted to meet up with him for some daytime fun. I said I’d love to but I’d have to arrange a day off work but I promised I’d get
back to him the following day.
The following evening Mike was online and I told him I’d been able to take the Friday off and so we arranged to meet at a pub close to my home that opened early.
One the Friday morning I made my way to the pub both anxious and excited. I’d never met a tv or cd before but I knew from chatting to Mike he was the right person to introduce me to this area of sexuality. It was only 9am and the pub was very quiet. There was only a pensioner and the barman and so I paid for a drink and sat down at a table. After about five minutes Mike came in. He was 5’6 with black hair and of a medium build. I made my way to the bar and said “Hi, what do you want to drink ?”. “A pint of lager” was his reply and so I ordered and paid for this and then motioned him to my table.
We sat down next to each other and Mike put his large holdall on the seat next to him. I’d already guessed it contained his clothes and he confirmed this. We chatted about nothing of any importance whilst we drank our drinks and when we
finished I said “Shall we ?” “Love to” was Mike’s reply.
We left the pub and made quick work of the short trip to my flat. Once inside I gave Mike a quick tour of the place and he said he wanted to go and get changed. I indicated he could do this in the spare bedroom. He departed with a “Don’t start without me”.
It took Mike 15 minutes to dress as he wished and he exited the bedroom and introduced herself. “Hi, I’m Michaela” she said. My eyes scanned Michaela. She had shoulder length blonde hair, make up just enough to accentuate her eyes
and lips. She wore a tight white blouse which only made the black bra below more obvious and enticing. She also had on a short black skirt which managed to show off her black hold ups as it was so short. The outfit was topped off with
the long black boots.
I said “You are stunning” meaning it. “Thank you” she said and I could see her start to blush. I asked Michaela if she minded if I took some photos and she said she love me to so I took a couple of shots there and then. That done we moved to each other and embraced. Our mouths moved together and I kissed Michaela deeply exploring her mouth and she submitted to my probing. She teased my tongue in her mouth and it brought a groan of pleasure from my throat. My hands explored her body stroking her back and moving down to her ass. Whilst
I was doing this Michaela had my ass in her hands and she was squeezing it and stroking it. I returned the favour and wormed my way under her skirt to stroke her along the line of her panties.
Michaela continued her explorations and undid my belt and loosened my jeans. She thrust her hand into my jeans and squealed with pleasure as she found I was not wearing underwear. She grasped my already hard cock and started rubbing it and jerking it.
“Do you want to suck me ?” I asked. “Yes please” was Michaela’s reply.
I slipped off my shoes and shed my trousers as Michaela got to her knees. She first licked around my bollocks and took first one and then both into her mouth. I had my camera in hand to photograph Michaela doing such great work. She
then moved upwards to my upstanding cock and licked up first the left and then the right side of it. She then moved higher and took my cockhead into her mouth. I groaned with pleasure and Michaela looked up at me with a smile in her eyes which I captured on camera.
Michaela proceeded to suck me and lick me and my engorged cockhead got harder and harder. Her head went up and down. Up and down. Up and down. Up and down. Up and down. She really knew how to work a cock; how to bring a cock to orgasm. And that is what she did. I could take no more and told her to prepare
for cum. She clung on tight to me as the cum spurted from my balls, up my shaft and shot out of my cockhead and into her mouth. Once, twice, three times I shot my hot seed into her mouth and she accepted it all like the wanton slut she is.
When I’d finished she stood up and kissed me hard. Her tongue and mouth were still plastered in my cum and I welcomed her returning it to me. We kissed deeply for a while exulting in the feeling and then I broke.
“Do you want to go to the bedroom ?” I asked. “Yes please”
she replied.
I took her by the hand and led her to my bedroom. She dutifully followed as we both sought to continue our pleasure.
I opened the door and indicated to her the king-size bed. “Make yourself comfortable” I said. I removed the rest of my clothing as Michaela removed her blouse. She climbed on the bed and lay there with her legs open displaying her
charms.
“You’ve still got your panties on you naughty bitch” I said. “I’ll have to remove them for you”
I climbed onto the bed and made my way to her panties. I slipped one hand on each side of the red lingerie and eased them down. Michaela aided me by moving her legs accordingly and soon the panties were over her boots and discarded on the floor. I moved back up over her and admired her cock. Like me, she
was cut and, like me, she was hard.
I needed no invitation and took her in my mouth. I sucked, first, her cockhead and then moved down and my head bobbed up and down. Sucking her harder and harder. “Suck my cock hard”, Michaela said, “I want to cum in your mouth”.
Hearing this I upped my efforts working rigorously on her. Licking and sucking. Whilst I was doing this I was stroking her asshole with my right index finger. Rubbing around it as I continued to work her cock. Then I thrust my finger
into her up to the knuckle. Michaela squealed in delight as I started to finger fuck her ass. Finger in and out as head bobbed up and down.
“Take my cum” Michaela said when she could take no more. Her cum pumped out of her balls, up her shaft and into my welcoming mouth. I gratefully received it and swallowed it as much as I could. When she’d done I moved up her torso to confront her face. She smiled and I kissed her hard giving her some
of her cum. We kissed deeply and passionately as we shared the outpourings of her pleasure.
We broke and I said to her, “now my sweet I want you to get on all fours as I’m going to fuck you as you as you rightfully desire and rightfully deserve.” Michaela obediently turned over and presented her ass to me. She wiggled it at
me as she looked back at me and I recovered the camera to get a couple of shots of the sexy sight.
I put down the camera and clambered onto the bed. I moved in close to her feeling the leather of her boots and the nylon of her hold ups against my thighs. In closer still until the head of my cock brushed her asshole. She shivered and I thrust. Into her I went. Slowly at first. Easing my way
in. Deeper and deeper as her ass swallowed the head of my cock. In further. She squealed with a mixture of pain and pleasure. In further. She groaned. In further. Until I was half the way in. In further. As she widened for me. In
fully as my balls slapped against her. Still tight but oh so welcoming.
“Fuck me hard, fuck me long, fuck me with your lovely cock. Stretch me and pump your cum in my ass.” I got the impression Michaela wanted more. So, not a man to disappoint, I withdrew my cock and then forced it back into her. She was tight but I’d stretch her as she desired.
Where we were positioned on the bed Michaela was facing a wide full length mirror and she could see my upper body and smiling face as I relentlessly pumped her ass. “Can we please turn so I can see the side on view of you fucking
me ?” she asked. “Sure thing baby, ” I replied.
We repositioned ourselves as Michaela had requested and I immediately recognised why she had requested this. I looked to my left and she did too and we could see her sexy rump and my cock as it went in and out of her. I could see the look of pleasure on her face and I redoubled my efforts. I wanted to give this sexy little slut the pleasure she deserved.
I fucked her fast. I fucked her slow. I changed my speed by withdrawing slowly and then slammed in quickly and hard. She loved it all. As did I. She loved cock and I loved giving her it.
We moved positions regularly as I continued to pound her wanton asshole. She rode me as I lay on my back, she lay on her side as I fucked her whilst spooning, I fucked her up against the mirror, I fucked her as she looked out the window and I fucked her as she lay on her back with her legs at her
shoulders.
“Please cum in me” she pleaded as her legs were by her shoulders and I was deep inside her. I moved in my face close to hers and said “beg me my slut”. “Please”, she replied, “I loved the taste of your cum and want it shooting in my ass. I’ll be your slut whenever you want just fuck me and cum in me.”
I responded by fucking her even harder and moved in to kiss her. She moved her mouth to mine and I thrust my tongue into her wanton orifice and subjugated her tongue. She was my slut and I was her master.
Then I felt it. That familiar stirring in my balls. I was going to cum. “Take it slut”, I told her, “take all my cum inside you.” At this my cum poured out of me. I thrust in deeper ensuring it went so deep inside her. I clung to her as I reduced my tempo until I lay there, my cock still in her cum filled
asshole. I kissed and her and said, “You are a great fuck.”
We took a breather and I took a few photographs of her lying on her back with the cum oozing out of her ass. It was so hot. Then she took some of it on a finger and took it to her lips to taste my cum again. Then she took some more and rubbed it on her cock slowly making her hard in the process. “Wanna
taste your cum ?” she asked with a glint in her eye. “Love to”, I replied as I clambered over her into a sixty nine.
And so we continued our first day of sheer pleasure together. The day was still young as it had only turned 10.30 and we had another five and a half hours of unadulterated pleasure to come with Michaela dressing in a number of different
outfits to tantalise me before demanding I fuck her.
What a first date that was.
He was married guy named Mike and he had a very understanding wife who allowed him to meet men and allow him to explore his feminine side by dressing up. His wife did not participate with him and none of his explorations happened at home.
During our chat he explained he’d just bought a pair of long, nearly thigh high, boots and he longed to be fucked whilst wearing them. He was off that week and wondered if I wanted to meet up with him for some daytime fun. I said I’d love to but I’d have to arrange a day off work but I promised I’d get
back to him the following day.
The following evening Mike was online and I told him I’d been able to take the Friday off and so we arranged to meet at a pub close to my home that opened early.
One the Friday morning I made my way to the pub both anxious and excited. I’d never met a tv or cd before but I knew from chatting to Mike he was the right person to introduce me to this area of sexuality. It was only 9am and the pub was very quiet. There was only a pensioner and the barman and so I paid for a drink and sat down at a table. After about five minutes Mike came in. He was 5’6 with black hair and of a medium build. I made my way to the bar and said “Hi, what do you want to drink ?”. “A pint of lager” was his reply and so I ordered and paid for this and then motioned him to my table.
We sat down next to each other and Mike put his large holdall on the seat next to him. I’d already guessed it contained his clothes and he confirmed this. We chatted about nothing of any importance whilst we drank our drinks and when we
finished I said “Shall we ?” “Love to” was Mike’s reply.
We left the pub and made quick work of the short trip to my flat. Once inside I gave Mike a quick tour of the place and he said he wanted to go and get changed. I indicated he could do this in the spare bedroom. He departed with a “Don’t start without me”.
It took Mike 15 minutes to dress as he wished and he exited the bedroom and introduced herself. “Hi, I’m Michaela” she said. My eyes scanned Michaela. She had shoulder length blonde hair, make up just enough to accentuate her eyes
and lips. She wore a tight white blouse which only made the black bra below more obvious and enticing. She also had on a short black skirt which managed to show off her black hold ups as it was so short. The outfit was topped off with
the long black boots.
I said “You are stunning” meaning it. “Thank you” she said and I could see her start to blush. I asked Michaela if she minded if I took some photos and she said she love me to so I took a couple of shots there and then. That done we moved to each other and embraced. Our mouths moved together and I kissed Michaela deeply exploring her mouth and she submitted to my probing. She teased my tongue in her mouth and it brought a groan of pleasure from my throat. My hands explored her body stroking her back and moving down to her ass. Whilst
I was doing this Michaela had my ass in her hands and she was squeezing it and stroking it. I returned the favour and wormed my way under her skirt to stroke her along the line of her panties.
Michaela continued her explorations and undid my belt and loosened my jeans. She thrust her hand into my jeans and squealed with pleasure as she found I was not wearing underwear. She grasped my already hard cock and started rubbing it and jerking it.
“Do you want to suck me ?” I asked. “Yes please” was Michaela’s reply.
I slipped off my shoes and shed my trousers as Michaela got to her knees. She first licked around my bollocks and took first one and then both into her mouth. I had my camera in hand to photograph Michaela doing such great work. She
then moved upwards to my upstanding cock and licked up first the left and then the right side of it. She then moved higher and took my cockhead into her mouth. I groaned with pleasure and Michaela looked up at me with a smile in her eyes which I captured on camera.
Michaela proceeded to suck me and lick me and my engorged cockhead got harder and harder. Her head went up and down. Up and down. Up and down. Up and down. Up and down. She really knew how to work a cock; how to bring a cock to orgasm. And that is what she did. I could take no more and told her to prepare
for cum. She clung on tight to me as the cum spurted from my balls, up my shaft and shot out of my cockhead and into her mouth. Once, twice, three times I shot my hot seed into her mouth and she accepted it all like the wanton slut she is.
When I’d finished she stood up and kissed me hard. Her tongue and mouth were still plastered in my cum and I welcomed her returning it to me. We kissed deeply for a while exulting in the feeling and then I broke.
“Do you want to go to the bedroom ?” I asked. “Yes please”
she replied.
I took her by the hand and led her to my bedroom. She dutifully followed as we both sought to continue our pleasure.
I opened the door and indicated to her the king-size bed. “Make yourself comfortable” I said. I removed the rest of my clothing as Michaela removed her blouse. She climbed on the bed and lay there with her legs open displaying her
charms.
“You’ve still got your panties on you naughty bitch” I said. “I’ll have to remove them for you”
I climbed onto the bed and made my way to her panties. I slipped one hand on each side of the red lingerie and eased them down. Michaela aided me by moving her legs accordingly and soon the panties were over her boots and discarded on the floor. I moved back up over her and admired her cock. Like me, she
was cut and, like me, she was hard.
I needed no invitation and took her in my mouth. I sucked, first, her cockhead and then moved down and my head bobbed up and down. Sucking her harder and harder. “Suck my cock hard”, Michaela said, “I want to cum in your mouth”.
Hearing this I upped my efforts working rigorously on her. Licking and sucking. Whilst I was doing this I was stroking her asshole with my right index finger. Rubbing around it as I continued to work her cock. Then I thrust my finger
into her up to the knuckle. Michaela squealed in delight as I started to finger fuck her ass. Finger in and out as head bobbed up and down.
“Take my cum” Michaela said when she could take no more. Her cum pumped out of her balls, up her shaft and into my welcoming mouth. I gratefully received it and swallowed it as much as I could. When she’d done I moved up her torso to confront her face. She smiled and I kissed her hard giving her some
of her cum. We kissed deeply and passionately as we shared the outpourings of her pleasure.
We broke and I said to her, “now my sweet I want you to get on all fours as I’m going to fuck you as you as you rightfully desire and rightfully deserve.” Michaela obediently turned over and presented her ass to me. She wiggled it at
me as she looked back at me and I recovered the camera to get a couple of shots of the sexy sight.
I put down the camera and clambered onto the bed. I moved in close to her feeling the leather of her boots and the nylon of her hold ups against my thighs. In closer still until the head of my cock brushed her asshole. She shivered and I thrust. Into her I went. Slowly at first. Easing my way
in. Deeper and deeper as her ass swallowed the head of my cock. In further. She squealed with a mixture of pain and pleasure. In further. She groaned. In further. Until I was half the way in. In further. As she widened for me. In
fully as my balls slapped against her. Still tight but oh so welcoming.
“Fuck me hard, fuck me long, fuck me with your lovely cock. Stretch me and pump your cum in my ass.” I got the impression Michaela wanted more. So, not a man to disappoint, I withdrew my cock and then forced it back into her. She was tight but I’d stretch her as she desired.
Where we were positioned on the bed Michaela was facing a wide full length mirror and she could see my upper body and smiling face as I relentlessly pumped her ass. “Can we please turn so I can see the side on view of you fucking
me ?” she asked. “Sure thing baby, ” I replied.
We repositioned ourselves as Michaela had requested and I immediately recognised why she had requested this. I looked to my left and she did too and we could see her sexy rump and my cock as it went in and out of her. I could see the look of pleasure on her face and I redoubled my efforts. I wanted to give this sexy little slut the pleasure she deserved.
I fucked her fast. I fucked her slow. I changed my speed by withdrawing slowly and then slammed in quickly and hard. She loved it all. As did I. She loved cock and I loved giving her it.
We moved positions regularly as I continued to pound her wanton asshole. She rode me as I lay on my back, she lay on her side as I fucked her whilst spooning, I fucked her up against the mirror, I fucked her as she looked out the window and I fucked her as she lay on her back with her legs at her
shoulders.
“Please cum in me” she pleaded as her legs were by her shoulders and I was deep inside her. I moved in my face close to hers and said “beg me my slut”. “Please”, she replied, “I loved the taste of your cum and want it shooting in my ass. I’ll be your slut whenever you want just fuck me and cum in me.”
I responded by fucking her even harder and moved in to kiss her. She moved her mouth to mine and I thrust my tongue into her wanton orifice and subjugated her tongue. She was my slut and I was her master.
Then I felt it. That familiar stirring in my balls. I was going to cum. “Take it slut”, I told her, “take all my cum inside you.” At this my cum poured out of me. I thrust in deeper ensuring it went so deep inside her. I clung to her as I reduced my tempo until I lay there, my cock still in her cum filled
asshole. I kissed and her and said, “You are a great fuck.”
We took a breather and I took a few photographs of her lying on her back with the cum oozing out of her ass. It was so hot. Then she took some of it on a finger and took it to her lips to taste my cum again. Then she took some more and rubbed it on her cock slowly making her hard in the process. “Wanna
taste your cum ?” she asked with a glint in her eye. “Love to”, I replied as I clambered over her into a sixty nine.
And so we continued our first day of sheer pleasure together. The day was still young as it had only turned 10.30 and we had another five and a half hours of unadulterated pleasure to come with Michaela dressing in a number of different
outfits to tantalise me before demanding I fuck her.
What a first date that was.
Safiya
- 19.08.2022
- 16
- 0
