Ladyboys Moving to Thailand and my first Ladyboy
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The Lady Is The Boss free porn video
I'm 35 and have worked for a marketing firm for over 8 years and in my time have had to attend many conferences and events, this is the story of my overnighter.
The firm I work for is run by a husband and wife, Kat (43) and Peter (48). Kat is fit for her age, a true professional woman with jet black hair, green eyes, pert tits and gorgeous legs. A lot of time is spent preparing pitches and travelling the country presenting them to various clients. Having only just started in marketing, I was a little green behind the ears, so Kat decided it would be good experience for me to shadow her on her next presentation in London. It would mean staying the night in a hotel after pitching, all on expenses of course!
We travelled down in Kat's Mercedes, exchanging small talk and got on really well. I couldn't help staring at Kat's legs clad in jet black stockings which were being revealed more and more as her skirt rode up her thighs as she drove. The skirt was matched by a black business suit and white undershirt, all which I imagine were from the very expensive shelf in a branded shop somewhere! We arrived at the pitch destination and I watched a true professional in action. Kat had them eating from her hand, working the clients with her knowledge and at times down right flirtatious nature, all this was increasing the respect I had for her and I still couldn't take my eyes off those long silky clad legs. Kat eventually wrapped up the presentation and after saying our goodbyes we travelled to our hotel in the outskirts of London.
We checked in, the time being around 7pm and made our way to our rooms, whose doors faced opposite each other. Just as I was going into my room Kat asked if I fancied going down to the bar later for a drink or three, I agreed and went into my room for a shower. Whist in the shower I started to play with my cock, thinking about Kat and having her legs wrapped around me as I fucked her, wanking myself off at the thought of my boss taking my load. It didn't take me long to cum thinking about those legs, I think I had what is known as a fixation!
I re showered and got dressed into a pair of smart trousers and shirt and started to watch TV, after a while my mobile rang, it was Kat asking me to go to her room for a drink. I locked my room, knocked Kat's door and she shouted to me to come in as it was open. Kat offered me a drink from the mini bar and we both sat and talked through the day, with me saying how much I admired her handling of the clients. She smiled and told me that compliments were the way to a woman's heart. As we talked there was a muffled noise from the room next door which gradually got louder and louder until it was obvious that someone in the next room was getting it on. I was a little embarrased and suggested to go down to the bar, but Kat said she didn't want to miss the climax of the show and put her ear to the wall so she could hear better. She motioned to me to do the same, so naturally I did as my boss asked.
Whoever was next door was really going at it, high and low pitch grunting with lots of yes shouts thrown in for good measure. As the woman next door came loudly, Kat seemed pleased, turned on in fact, and told me that she now needed that drink whilst also telling me that she could do with a pint of whatever the couple next door were on. We made our way down to the bar and ordered the first of a few drinks. We sat on stools at the bar, Kat perched on the edge of her's, again wearing sheer black stockings. But this time with strappy high heels, and a japanese style figure hugging red dress with dragon/flower stitching on.
Kat told me the rule for the night now was no work talk, to which I agreed and we started small talk again. All of a sudden Kat brought up the couple in the next room to her's again and out of the blue asked me if I was turned on by listening to them. I couldn't lie and said yes, asking her the same question, to which she answered yes also. She then started to ask me about my sex life, what my preferences were, positions I liked, type of woman I went for. We were at the point of not drunk but tipsy enough for daring conversation to enter the fray, so I asked her if she had ever had an affair away from Peter. She told me she had had hundreds but also that Peter was well aware and had adventures of his own and that the overnighters were a banker for sex. So I asked if she wanted me to leave her and not cramp her style, she replied no and in return I asked if anyone in the bar caught her eye. Kat answered that there was a guy she liked the look of and asked if she would like her to describe him to me. I nodded and she proceeded to describe the clothes I was in and how I looked, I was a little shocked but also excited to the core.
Kat told me that there was no pressure and she was going up to her room, but if I did fancy an 'adventure' to join her in 10 mins. My heart was racing, questions kept rolling over in my head, such as could I face her at work if we had sex? I mulled them over and decided after 10 mins to go up to Kat's room, I knocked and there was no answer, so I knocked again, no answer. I tried the door which I found to be unlocked and as I walked into the room I found Kat on her bed fully dressed, fucking herself with a dildo whilst listening to the couple next door who had started up again. She looked up at me and told me she was sorry but she had started without me as she couldn't read from my body language if I would make an appearance or not.
She handed me the dildo, black and around 7 inches and asked me to do the honours, to which I nodded. Kat opened her legs as I kissed them through her stockings, whilst I started to tease the edge of her pussy lips and clit by running and rolling the full length of the dildo over them. Then I turned it onto the slowest setting, pushing it's revolving head hard against the edge of Kat's moist pussy making her gasp. Then my tongue joined in the action, licking and sucking pussy juices from the dildo's shaft much to Kat's delight as she watched. I then pushed the full length of the dildo inside her, alternating the speeds as I thrust it up and down whilst Kat fingered her clit. She soon came, her whole body tightening as she yelled out in ecstasy and after a while she sat up and told me it was my turn.
Kat teased down my trousers and boxer shorts and told me to sit on the edge of the bed whilst she went and got a chair and sat in front of me. I was still coming to terms with the fact i'd just made my boss cum let alone the fact she was now admiring my raging hard on as I sat in front of her! Kat slowly raised her feet towards my cock and carefully positioned it between the heels of her shoes, slowly starting to wank me with long deliberate strokes. My cock was pulsing and after a while she removed her shoes and continued to wank me with the soles of her stocking clad feet again slow and deliberate stokes, letting me feel the sheer nylon on the skin of my cock. Then Kat moved her right foot under my ball sack and began to gentley rub it with the top of her foot whilst playing with the tip of my cock with her toes on her left foot.
Kat then said she would love to feel me inside her and directed me to sit on the chair as she straddled me and felt for my cock, positioning it so she could lower herself onto it, groaning as she did. We started to fuck, hard, as if it was going to be the last fuck we had together, the pace was fast and Kat's hands found their way under my shirt and her nail extensions scratched my back as she rode me. She told me to pull her hair, which I did forcing her head backwards and with the other hand pushing down on her shoulder so my cock plunged deeper inside her. Our hips were bucking and circling our bodies hot from effort and enjoyment. I started to suck her nipples through the material of her dress, eventually biting as my primal instincts started to take over. Kat pulled my hands onto her arse, asking me to play with it, I obliged but just teased her on the upstroke by pulling her arse cheeks apart and barely touching her rim with the tip of one of my fingers, just enough to let her know it was there. This drove her over the edge again as she came, I let her have more finger as she did which her arse greedly enveloped, again after a while she regained composure.
She returned to her foot job position and started to wank me again, this time more vigourously encouraging me to come over her, it didn't take long and as I did she held my foreskin right back with her feet so my cum shot further. It landed on her dress and stockings with the last drips coating her feet and toes, she slowly removed each stocking and wiped them over her pussy and then my cock.
We both lay back on the bed, fulfilled and happy, and Kat asked if i'd like to shadow her again sometime!
The firm I work for is run by a husband and wife, Kat (43) and Peter (48). Kat is fit for her age, a true professional woman with jet black hair, green eyes, pert tits and gorgeous legs. A lot of time is spent preparing pitches and travelling the country presenting them to various clients. Having only just started in marketing, I was a little green behind the ears, so Kat decided it would be good experience for me to shadow her on her next presentation in London. It would mean staying the night in a hotel after pitching, all on expenses of course!
We travelled down in Kat's Mercedes, exchanging small talk and got on really well. I couldn't help staring at Kat's legs clad in jet black stockings which were being revealed more and more as her skirt rode up her thighs as she drove. The skirt was matched by a black business suit and white undershirt, all which I imagine were from the very expensive shelf in a branded shop somewhere! We arrived at the pitch destination and I watched a true professional in action. Kat had them eating from her hand, working the clients with her knowledge and at times down right flirtatious nature, all this was increasing the respect I had for her and I still couldn't take my eyes off those long silky clad legs. Kat eventually wrapped up the presentation and after saying our goodbyes we travelled to our hotel in the outskirts of London.
We checked in, the time being around 7pm and made our way to our rooms, whose doors faced opposite each other. Just as I was going into my room Kat asked if I fancied going down to the bar later for a drink or three, I agreed and went into my room for a shower. Whist in the shower I started to play with my cock, thinking about Kat and having her legs wrapped around me as I fucked her, wanking myself off at the thought of my boss taking my load. It didn't take me long to cum thinking about those legs, I think I had what is known as a fixation!
I re showered and got dressed into a pair of smart trousers and shirt and started to watch TV, after a while my mobile rang, it was Kat asking me to go to her room for a drink. I locked my room, knocked Kat's door and she shouted to me to come in as it was open. Kat offered me a drink from the mini bar and we both sat and talked through the day, with me saying how much I admired her handling of the clients. She smiled and told me that compliments were the way to a woman's heart. As we talked there was a muffled noise from the room next door which gradually got louder and louder until it was obvious that someone in the next room was getting it on. I was a little embarrased and suggested to go down to the bar, but Kat said she didn't want to miss the climax of the show and put her ear to the wall so she could hear better. She motioned to me to do the same, so naturally I did as my boss asked.
Whoever was next door was really going at it, high and low pitch grunting with lots of yes shouts thrown in for good measure. As the woman next door came loudly, Kat seemed pleased, turned on in fact, and told me that she now needed that drink whilst also telling me that she could do with a pint of whatever the couple next door were on. We made our way down to the bar and ordered the first of a few drinks. We sat on stools at the bar, Kat perched on the edge of her's, again wearing sheer black stockings. But this time with strappy high heels, and a japanese style figure hugging red dress with dragon/flower stitching on.
Kat told me the rule for the night now was no work talk, to which I agreed and we started small talk again. All of a sudden Kat brought up the couple in the next room to her's again and out of the blue asked me if I was turned on by listening to them. I couldn't lie and said yes, asking her the same question, to which she answered yes also. She then started to ask me about my sex life, what my preferences were, positions I liked, type of woman I went for. We were at the point of not drunk but tipsy enough for daring conversation to enter the fray, so I asked her if she had ever had an affair away from Peter. She told me she had had hundreds but also that Peter was well aware and had adventures of his own and that the overnighters were a banker for sex. So I asked if she wanted me to leave her and not cramp her style, she replied no and in return I asked if anyone in the bar caught her eye. Kat answered that there was a guy she liked the look of and asked if she would like her to describe him to me. I nodded and she proceeded to describe the clothes I was in and how I looked, I was a little shocked but also excited to the core.
Kat told me that there was no pressure and she was going up to her room, but if I did fancy an 'adventure' to join her in 10 mins. My heart was racing, questions kept rolling over in my head, such as could I face her at work if we had sex? I mulled them over and decided after 10 mins to go up to Kat's room, I knocked and there was no answer, so I knocked again, no answer. I tried the door which I found to be unlocked and as I walked into the room I found Kat on her bed fully dressed, fucking herself with a dildo whilst listening to the couple next door who had started up again. She looked up at me and told me she was sorry but she had started without me as she couldn't read from my body language if I would make an appearance or not.
She handed me the dildo, black and around 7 inches and asked me to do the honours, to which I nodded. Kat opened her legs as I kissed them through her stockings, whilst I started to tease the edge of her pussy lips and clit by running and rolling the full length of the dildo over them. Then I turned it onto the slowest setting, pushing it's revolving head hard against the edge of Kat's moist pussy making her gasp. Then my tongue joined in the action, licking and sucking pussy juices from the dildo's shaft much to Kat's delight as she watched. I then pushed the full length of the dildo inside her, alternating the speeds as I thrust it up and down whilst Kat fingered her clit. She soon came, her whole body tightening as she yelled out in ecstasy and after a while she sat up and told me it was my turn.
Kat teased down my trousers and boxer shorts and told me to sit on the edge of the bed whilst she went and got a chair and sat in front of me. I was still coming to terms with the fact i'd just made my boss cum let alone the fact she was now admiring my raging hard on as I sat in front of her! Kat slowly raised her feet towards my cock and carefully positioned it between the heels of her shoes, slowly starting to wank me with long deliberate strokes. My cock was pulsing and after a while she removed her shoes and continued to wank me with the soles of her stocking clad feet again slow and deliberate stokes, letting me feel the sheer nylon on the skin of my cock. Then Kat moved her right foot under my ball sack and began to gentley rub it with the top of her foot whilst playing with the tip of my cock with her toes on her left foot.
Kat then said she would love to feel me inside her and directed me to sit on the chair as she straddled me and felt for my cock, positioning it so she could lower herself onto it, groaning as she did. We started to fuck, hard, as if it was going to be the last fuck we had together, the pace was fast and Kat's hands found their way under my shirt and her nail extensions scratched my back as she rode me. She told me to pull her hair, which I did forcing her head backwards and with the other hand pushing down on her shoulder so my cock plunged deeper inside her. Our hips were bucking and circling our bodies hot from effort and enjoyment. I started to suck her nipples through the material of her dress, eventually biting as my primal instincts started to take over. Kat pulled my hands onto her arse, asking me to play with it, I obliged but just teased her on the upstroke by pulling her arse cheeks apart and barely touching her rim with the tip of one of my fingers, just enough to let her know it was there. This drove her over the edge again as she came, I let her have more finger as she did which her arse greedly enveloped, again after a while she regained composure.
She returned to her foot job position and started to wank me again, this time more vigourously encouraging me to come over her, it didn't take long and as I did she held my foreskin right back with her feet so my cum shot further. It landed on her dress and stockings with the last drips coating her feet and toes, she slowly removed each stocking and wiped them over her pussy and then my cock.
We both lay back on the bed, fulfilled and happy, and Kat asked if i'd like to shadow her again sometime!
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- 25.09.2021
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- Category:
- Straight Sex
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