Lingerie Salesman
- 4 years ago
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The Lingerie Salesman (Sissy) free porn video
I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had the most amazing threesome every two weeks. My best customer was Vera who was early 60s but she rewarded me with the most amazing sex and introduced me to the joys of anal sex.
Then things changed. There was a new resident and so I needed to ring that bell. A young man answered. Now I’m not gay but there was something about the man that was different. “Is your wife or girlfriend in?” I asked. He explained that he was single and unattached. “What are you selling though? I might be interested.” I laughed. “I doubt it. My case is full of women’s lingerie.” He laughed too. “I don’t think so.” Now I was the company’s top salesman and during my free time I sold fridges to Eskimos. Joke. “Why don’t I show you anyway to see what you think?” He smiled and showed me into the lounge. As he sat next to me I opened my case. “These panties are really pretty, pink lace and little red flowers around the top.” He noted how soft the lace was. “Wish I had someone to buy these for. I bet she would look so sexy,” he said as he caressed the material. Then it came out of my mouth. “Why don’t you try on the panties. The soft material makes them so comfortable.” He looked surprised but then he agreed. “Why not? It might be a bit of fun.” He stripped off in front of me. He did have a nice body with smooth skin but I was not interested in guys so it did not bother me. However, this all changed when he put the panties on. In short he looked very sexy and feminine. “Walk around and see how they feel.” He did so and he did look good. “I love them. They feel nice and I feel like I’m a different person.” I was seeing him quite differently and I wasn’t looking at him as a guy because the pink panties gave him a certain femininity. “Why don’t you put the bra on as it is a matching set?” He smiled and I helped him fasten the pink lace bra. He started to walk around again and he even started to wiggle his bum. Neither of us were gay but he had ceased to be a man. His bum was cuter than many of the ladies whose tight rear hole I had enjoyed. The pink bra and panties suited him and I could tell I liked what I saw as I was getting an erection. I reached into my case and found some hold-up sheer black stockings. He smiled when he saw them. “This bra and panties set does not have a matching suspender belt but you can wear hold-ups. Roll the stockings up your legs to mid-thigh. Your legs are so smooth so they will make you feel good.” He did as he was told. I had friends who had sissy girlfriends and I could tell why now and I had not even fucked her yet. "Her" because she was certainly a sissy and "yet" because that gorgeous bum hole was going to get a good, hard shagging. Now I realised this was a “she” I called her over. “Come and sit on my lap.” She looked at me and smiled. “My ex-girlfriend left some things here. Give me a few minutes and I’ll see what I can do.” The sissy had clearly realised that the lingerie and stockings suited her.
About ten minutes later she returned and she looked even sexier. She wore a black mini skirt with a white blouse and she had black high heels as her girlfriend must have been about the same size. She had even found a red lipstick. She walked around the room, a little unsteady in her heels but clearly relishing being a sissy. “You look incredible, so feminine and sexy,” I noted aware that I was hard. She smiled her sexy smile at me, “so you think so? I feel so different, sexy, feminine and relaxed.” She then came and sat in my lap and I put my arm around her. “You are such a natural sissy,” I said as I caressed her nylon-clad thigh. “I suppose so. It feels so natural and I have wasted so many years denying the reality,” she replied as her natural submissiveness meant that her legs parted as I moved my hand to her stocking tops. “This feels natural for me too my darling,” I said. “You are so pretty and sexy and I’ve never been with a sissy too, only natural women.” We started to kiss and it was amazing, even better than kissing a natural woman. As our tongues entwined in a beautiful French kiss my hand caressed the front of her panties and I felt her bulge. I had no desire to touch a man's cock but she was a sissy and it felt nice having my hand there. I pushed my hand around the back and pushed a finger gently into her tight sex hole. "Mmm, that feels nice," she moaned as I worked my finger inside her. "Why don't you get on your knees darling and we can see if you are a good girl?" She knelt in front of me and looked up. She looked amazing and I was going to enjoy her, learning about sissies as I did. I undid my trousers and my hard cock popped out. She looked at it and then started to run her hand up and down the shaft. "I've never done this before," she said. I laughed. "My neither, I've never had a sissy but you are going to suck my cock now and show me just how good a girl you are." She licked around the tip and then took the whole cock between her lips. "Good girl, take it all in your mouth." She soon proved she could suck cock although I did have to tell her to lick my balls too. "You're enjoying this aren't you, little whore." She nodded. "I really like cock I guess," she replied. I was going to cum and I held the back of her head. "Swallow all my cum you dirty bitch." And she did so, licking her lips afterwards. She then sat back on my lap and we kissed again. "That was amazing sir," she said with her sexy eyes sparkling. "I'm actually a chef so will you stay and I'll cook you a nice meal." I squeezed her bum. "I'd love that my darling and I will take your virginity later."
I watched the TV and drank a beer while she busied herself in the kitchen. After a short while I joined her. She was chopping vegetables. I put my arms around her waist and started to kiss her neck. "Mmm, sir, that's nice." She backed into me and I knew she needed cock, after all what is more natural for a sissy? "I can't call you Derek any more, can I as you're a sissy, a girl? I think you should be Linda as that's a nice name." She agreed. I pushed a hand up her skirt and started to caress her bum. "You know darling. I can't wait. I'm going to fuck you now." I actually had some lube in my pocket and I applied a liberal amount to her cunt. "Oooh that's cold." Well, cold lube for a hot sissy. My cock was nice and hard. I pulled her panties down and she bent over the worktop. "Are you ready to lose your virginity Linda, my darling?" She pushed her bum back. "Yes sir, please make me a woman." I eased into her. She was tight but the lube had done it's job. "Oh sir, gently, that does hurt a bit." I pulled back and then pushed harder into her. "Oh Linda, you are such a beautiful WOMAN." I stressed the last word as she was now a woman, a beautiful sissy that men would enjoy. I started a steady fucking rhythm. "Oh that Oooh, feels so FUCK, good." She was good too. "Linda you are so beautiful, so sexy and even on your first time a great fuck. You are a natural sissy." As I pushed into her she responded by pushing her bum backwards to meet my cock. She did need to be fucked. I now knew that my life would be with sissies now as her tight cunt felt so wonderful and she was so naturally submissive. After a few minutes I could feel the cum building up. "I'm going to cum in your cunt my darling just to make it 100% clear that you are now a woman. "Yes, sir, please, fuck that's so good." Her back arched as she achieved a natural sissy orgasm on her first fuck and I released my seed into her. "Now get on your knees and clean the cum off my cock Linda." She did as she was told and admitted she liked the taste of my cum. "That's good," I told her, "as you'll be getting a stomachful of that after dinner." I took a photo of my cum oozing from her sissy cunt before she pulled up her panties. "That's the proof you are a woman now." We kissed again.
Two hours larer we are cuddled up on the sofa. She had shown she was an amazing cook and she had the knack of keeping my cock hard too. After dinner she sucked me off to completion and, surprise surprise, she was an amazing cocksucker, swallowing every last drop of cum. We downloaded some transvestite videos to watch and she was fascinated. "Sir, I feel so wonderful as a sissy. I am feminine, sexy and when you fucked me it was the best thing ever. I wish I could be a girl all the time." It made a lot of sense. My friends had discussed whether sissies were born or created but this girl was so natural and was so feminine seemingly without trying. I kissed her again, "Linda my darling, you are so beautiful, so sexy, an amazing cook and a very good fuck. I want you to be my girlfriend." She agreed without hesitation. I was so excited about dressing her in beautiful clothes and showing her off to friends. "As I'm staying the night with you now I have a present for you." She hadn't asked me to stay but it was already clear she wanted me to take the lead. I reached into my case and handed her a package. "Now go and put this on my darling and let me see how you look." As she left the living room I couldn't take my eyes off her bum, so sexy and due for another good fucking in bed later. Ten minutes later the girl returned. She looked even better than I had expected. "WOW!" I exclaimed. "You look incredible Linda." She walked around the room in the sexiest white lace babydoll nightil. She wiggled her bum, clearly looking forward to my cock in her cunt again later. "Am I a good girlfriend sir?" she asked playfully. I smiled, "you certainly are my darling. I suggest we go to bed now as you need some serious attention." I took her hand and led her upstairs. She showed me to her bedroom which was still a male's but that would change. She undressed me and then I pulled her close. As we kissed again I caressed her bum cheeks and then pushed my hand inside her panties and a finger into her sissy cunt. That night we did not have sex, we made love. It was amazing. She came several times and I emptied another load of cum into her delicious cunt before we fell asleep together.
The following morning she proved me that she was a natural by showing me what I learned was the sissy alarm clock. I woke to the feel of her soft lips on my cock, making me instantly hard again. I took her out dressed as she was totally passable and bought her some new outfits. Within three weeks she had moved in with me. We were then invited to parties where my friends enjoyed Linda's charms while I also was able to become aquainted with the other sissies. A short while later I was promoted to sales director of the lingerie company. By now Linda had given up her job and was so much the perfect housewife that she became one. We were married at a stately home and she has constantly proved that a natural sissy is the perfect wife, a lady in company, a chef in the kitchen and a whore in the bedroom, well a whore everywhere as her constant sexual availability kept me busy and extremely happy.
Then things changed. There was a new resident and so I needed to ring that bell. A young man answered. Now I’m not gay but there was something about the man that was different. “Is your wife or girlfriend in?” I asked. He explained that he was single and unattached. “What are you selling though? I might be interested.” I laughed. “I doubt it. My case is full of women’s lingerie.” He laughed too. “I don’t think so.” Now I was the company’s top salesman and during my free time I sold fridges to Eskimos. Joke. “Why don’t I show you anyway to see what you think?” He smiled and showed me into the lounge. As he sat next to me I opened my case. “These panties are really pretty, pink lace and little red flowers around the top.” He noted how soft the lace was. “Wish I had someone to buy these for. I bet she would look so sexy,” he said as he caressed the material. Then it came out of my mouth. “Why don’t you try on the panties. The soft material makes them so comfortable.” He looked surprised but then he agreed. “Why not? It might be a bit of fun.” He stripped off in front of me. He did have a nice body with smooth skin but I was not interested in guys so it did not bother me. However, this all changed when he put the panties on. In short he looked very sexy and feminine. “Walk around and see how they feel.” He did so and he did look good. “I love them. They feel nice and I feel like I’m a different person.” I was seeing him quite differently and I wasn’t looking at him as a guy because the pink panties gave him a certain femininity. “Why don’t you put the bra on as it is a matching set?” He smiled and I helped him fasten the pink lace bra. He started to walk around again and he even started to wiggle his bum. Neither of us were gay but he had ceased to be a man. His bum was cuter than many of the ladies whose tight rear hole I had enjoyed. The pink bra and panties suited him and I could tell I liked what I saw as I was getting an erection. I reached into my case and found some hold-up sheer black stockings. He smiled when he saw them. “This bra and panties set does not have a matching suspender belt but you can wear hold-ups. Roll the stockings up your legs to mid-thigh. Your legs are so smooth so they will make you feel good.” He did as he was told. I had friends who had sissy girlfriends and I could tell why now and I had not even fucked her yet. "Her" because she was certainly a sissy and "yet" because that gorgeous bum hole was going to get a good, hard shagging. Now I realised this was a “she” I called her over. “Come and sit on my lap.” She looked at me and smiled. “My ex-girlfriend left some things here. Give me a few minutes and I’ll see what I can do.” The sissy had clearly realised that the lingerie and stockings suited her.
About ten minutes later she returned and she looked even sexier. She wore a black mini skirt with a white blouse and she had black high heels as her girlfriend must have been about the same size. She had even found a red lipstick. She walked around the room, a little unsteady in her heels but clearly relishing being a sissy. “You look incredible, so feminine and sexy,” I noted aware that I was hard. She smiled her sexy smile at me, “so you think so? I feel so different, sexy, feminine and relaxed.” She then came and sat in my lap and I put my arm around her. “You are such a natural sissy,” I said as I caressed her nylon-clad thigh. “I suppose so. It feels so natural and I have wasted so many years denying the reality,” she replied as her natural submissiveness meant that her legs parted as I moved my hand to her stocking tops. “This feels natural for me too my darling,” I said. “You are so pretty and sexy and I’ve never been with a sissy too, only natural women.” We started to kiss and it was amazing, even better than kissing a natural woman. As our tongues entwined in a beautiful French kiss my hand caressed the front of her panties and I felt her bulge. I had no desire to touch a man's cock but she was a sissy and it felt nice having my hand there. I pushed my hand around the back and pushed a finger gently into her tight sex hole. "Mmm, that feels nice," she moaned as I worked my finger inside her. "Why don't you get on your knees darling and we can see if you are a good girl?" She knelt in front of me and looked up. She looked amazing and I was going to enjoy her, learning about sissies as I did. I undid my trousers and my hard cock popped out. She looked at it and then started to run her hand up and down the shaft. "I've never done this before," she said. I laughed. "My neither, I've never had a sissy but you are going to suck my cock now and show me just how good a girl you are." She licked around the tip and then took the whole cock between her lips. "Good girl, take it all in your mouth." She soon proved she could suck cock although I did have to tell her to lick my balls too. "You're enjoying this aren't you, little whore." She nodded. "I really like cock I guess," she replied. I was going to cum and I held the back of her head. "Swallow all my cum you dirty bitch." And she did so, licking her lips afterwards. She then sat back on my lap and we kissed again. "That was amazing sir," she said with her sexy eyes sparkling. "I'm actually a chef so will you stay and I'll cook you a nice meal." I squeezed her bum. "I'd love that my darling and I will take your virginity later."
I watched the TV and drank a beer while she busied herself in the kitchen. After a short while I joined her. She was chopping vegetables. I put my arms around her waist and started to kiss her neck. "Mmm, sir, that's nice." She backed into me and I knew she needed cock, after all what is more natural for a sissy? "I can't call you Derek any more, can I as you're a sissy, a girl? I think you should be Linda as that's a nice name." She agreed. I pushed a hand up her skirt and started to caress her bum. "You know darling. I can't wait. I'm going to fuck you now." I actually had some lube in my pocket and I applied a liberal amount to her cunt. "Oooh that's cold." Well, cold lube for a hot sissy. My cock was nice and hard. I pulled her panties down and she bent over the worktop. "Are you ready to lose your virginity Linda, my darling?" She pushed her bum back. "Yes sir, please make me a woman." I eased into her. She was tight but the lube had done it's job. "Oh sir, gently, that does hurt a bit." I pulled back and then pushed harder into her. "Oh Linda, you are such a beautiful WOMAN." I stressed the last word as she was now a woman, a beautiful sissy that men would enjoy. I started a steady fucking rhythm. "Oh that Oooh, feels so FUCK, good." She was good too. "Linda you are so beautiful, so sexy and even on your first time a great fuck. You are a natural sissy." As I pushed into her she responded by pushing her bum backwards to meet my cock. She did need to be fucked. I now knew that my life would be with sissies now as her tight cunt felt so wonderful and she was so naturally submissive. After a few minutes I could feel the cum building up. "I'm going to cum in your cunt my darling just to make it 100% clear that you are now a woman. "Yes, sir, please, fuck that's so good." Her back arched as she achieved a natural sissy orgasm on her first fuck and I released my seed into her. "Now get on your knees and clean the cum off my cock Linda." She did as she was told and admitted she liked the taste of my cum. "That's good," I told her, "as you'll be getting a stomachful of that after dinner." I took a photo of my cum oozing from her sissy cunt before she pulled up her panties. "That's the proof you are a woman now." We kissed again.
Two hours larer we are cuddled up on the sofa. She had shown she was an amazing cook and she had the knack of keeping my cock hard too. After dinner she sucked me off to completion and, surprise surprise, she was an amazing cocksucker, swallowing every last drop of cum. We downloaded some transvestite videos to watch and she was fascinated. "Sir, I feel so wonderful as a sissy. I am feminine, sexy and when you fucked me it was the best thing ever. I wish I could be a girl all the time." It made a lot of sense. My friends had discussed whether sissies were born or created but this girl was so natural and was so feminine seemingly without trying. I kissed her again, "Linda my darling, you are so beautiful, so sexy, an amazing cook and a very good fuck. I want you to be my girlfriend." She agreed without hesitation. I was so excited about dressing her in beautiful clothes and showing her off to friends. "As I'm staying the night with you now I have a present for you." She hadn't asked me to stay but it was already clear she wanted me to take the lead. I reached into my case and handed her a package. "Now go and put this on my darling and let me see how you look." As she left the living room I couldn't take my eyes off her bum, so sexy and due for another good fucking in bed later. Ten minutes later the girl returned. She looked even better than I had expected. "WOW!" I exclaimed. "You look incredible Linda." She walked around the room in the sexiest white lace babydoll nightil. She wiggled her bum, clearly looking forward to my cock in her cunt again later. "Am I a good girlfriend sir?" she asked playfully. I smiled, "you certainly are my darling. I suggest we go to bed now as you need some serious attention." I took her hand and led her upstairs. She showed me to her bedroom which was still a male's but that would change. She undressed me and then I pulled her close. As we kissed again I caressed her bum cheeks and then pushed my hand inside her panties and a finger into her sissy cunt. That night we did not have sex, we made love. It was amazing. She came several times and I emptied another load of cum into her delicious cunt before we fell asleep together.
The following morning she proved me that she was a natural by showing me what I learned was the sissy alarm clock. I woke to the feel of her soft lips on my cock, making me instantly hard again. I took her out dressed as she was totally passable and bought her some new outfits. Within three weeks she had moved in with me. We were then invited to parties where my friends enjoyed Linda's charms while I also was able to become aquainted with the other sissies. A short while later I was promoted to sales director of the lingerie company. By now Linda had given up her job and was so much the perfect housewife that she became one. We were married at a stately home and she has constantly proved that a natural sissy is the perfect wife, a lady in company, a chef in the kitchen and a whore in the bedroom, well a whore everywhere as her constant sexual availability kept me busy and extremely happy.
Aeryn
- 05.07.2021
- 58
- 0
