Straight Male / 50
Ever since I was about 18-20yo and knew enough about sex to be dangerous, I have had this fetish for women being all dressed up in some way to have sex. The only way I really got off was them to be dressed like a hooker. Sexy outfits with high heels or boots. I have absolutely no desire just to make love to a woman being naked, it does nothing to excite me no matter how beautiful the woman might be.
As I grew up and had relationships some of my girlfriends would indulge my fetishes, and even one of my two wives did as well. My wife passed away and I found myself back on the dating scene once again. Now finding a mature gal that likes the things I do is anything but easy. Most women in their 50's don't even want to get near a pair of high heels, much less wear them for the purposes of having sex.
After several months of dating women and not being satisfied sexually, I began to get desperate. I heard about the website called Craigslist. I knew it was a website people went to if they wanted to sell something, I never realized that people were also selling themselves on there as well.
I began to look through the postings, and hell I could even be direct and upfront what I was looking for. I didn't have to worry how I was going to tell the woman what I wanted sexually from her. It was either yes or no and then I would just move onto the next posting.
Of course the majority of the women were prostitutes and they would give me whatever I wanted for s rather premium price. I didn't want that, I wanted a relationship with a woman that would indulge my fetishes. Weeks and months went by until one night I got a response to my posting.
Her name was Valerie and she was about ten years younger than me. She included a picture with her wearing something very sexy and she told me she loved wearing those things because it made her feel sexy as well. So I emailed her back and told her I wanted a relationship, it wasn't just about the sex. She told me that's what she was looking for as well and we decided to meet.
We met the next week at a local bar that was about half way between her place and mine. Valerie was very pretty and had a nice body. She wore a rather snug fitting top that accented her large breasts, jeans and black knee boots over them. After our introduction we found a booth over in the corner of the bar to talk.
The booths were dimly lit with a candle glowing in the middle of the table. As we talked, there was just something about Valerie that wasn't right for some reason. She looked sexy as hell without a doubt, but something was off just a bit I couldn't figure out.
We had several drinks and a band rolled in about an hour later to play. We hung out, had a few more drinks and even danced a little bit which Valerie really enjoyed. She said her last boyfriend refused to dance with her. By 2am the bar was closing and we had to leave.
Standing between our cars, Valerie kissed me and put her hand on my crotch. We hadn't really planned anything about getting together as yet. Valerie whispered in my ear that she just happened to have an overnight bag in her car in case she was invited to my house. I let it be known she was definitely invited!
Valerie followed me to my house and after a brief make out session she asked to use the bathroom to freshen up. So I showed her where it was and a few minutes later I heard the shower running. I figured I would do the same while she was getting cleaned up, but first I lit some candles and killed the lights.
When I came out, Valerie was stretched out on the sofa. She had a glass of wine in her hand and had another glass sitting of the coffee table for me. It was hard to care about the wine when I saw how she was dressed. She had on this camisole that could barely contain her ample breasts, even in the dimly lit room I could see her nipples that protruded from behind the shiny material. She had on a matching pair of panties with stockings and a pair of black patent pumps on her feet. Frankly I could care less about the wine at this very moment.
We started to make out before the wine glasses were empty. The taste of her lipstick was on the tip of my tongue as the excitement began to build between my legs. I fondled her breasts and the tiny string holding the camisole closed somehow became undone. I began to kiss her breasts and nipples and saw the marks from her implant surgery underneath during my advances.
Valerie's hand found it's mark between my legs and with a bit of rubbing had me hard as steel. She coaxed me out of my jeans without much effort and I watched her painted lips slide down the length of my shaft. It had been a very long time since I had been with a woman, and to say I was ready would be an understatement.
We managed to make our way to the bedroom fairly quickly, Valerie was as aroused as I was by her actions. We made out some more, her tongue swirling around my mouth frantically, and I reciprocated as well. Her hand found my cock again and began to stroke me as we kissed.
I reached down, spreading her sexy legs and put my hand down into her panties a moment later. The first thing I would have noticed was she was shaved, but there was something else that felt different. There wasn't a opening I had expected to feel, it was a bump of some kind.
I sat up in bed and pulled her panties down slightly. The bedroom was dark but the street lights made enough light in the bedroom to see well enough. Valerie reached down and untucked her semi hard cock at this moment. There it was half erect in her hand, almost as big as my own cock. I sat in shock as she stroked it, wiggled it, as if to get the blood into it quicker. It became hard as my own in moments and Valerie moaned in pleasure jerking her own cock.
"Please don't stop now." Valerie sat up in bed and onto her knees next to me. She put her arms around my neck and kissed my face. I couldn't take my eyes off of her cock and it stuck straight out next to me. "Please don't reject me" she whispered into my ear.
I sat frozen in the darkness. What the hell had I done, what had I got myself into because of my fetish. "Please don't make me go," Valerie whispered. I wanted her to go, I was cursing myself in my mind for dealing with my own demons I didn't ever understand since I was a kid.
I reached out and brought my hand underneath her semi hard cock and lay it in the palm of my hand. Valerie wrapped her arm around my neck a bit more as we both tried to guess what my next move would be. "Please don't stop." Her voice was pleading, like a child that really wanted something she couldn't have.
Valerie told me to kneel up in bed and face her. She kissed me again, but my mind was trying to sort all of this out now. Suddenly I felt her hand around my cock as she continued to kiss me. At first there was no reaction. but the more she stroked it the blood found it's way and I began to get hard.
She kissed me harder and I began to get lost in the moment. Soon I was hard as steel again when I realized the warm sensation against my hardness. Valerie was holding her own cock as well as my own in her hand. She rubbed them together and stroked them in unison. I began to breathe faster just as she was as well. I couldn't bring myself to look, but I saw it in my mind. Her cock and mine clasped together in sexual lust, and I allowed her to keep going.
In the darkness Valerie took my hand and guided it to where hers was now. She took our cocks and guided them into my hand a moment later. My hand wrapped around our cocks and I squeezed us gently, Valerie kissed me again and moaned with pleasure. I reached down with my other hand and held our cocks even more tightly, Valerie started to move her hips with her hard cock within my grasp. The sensation against my cock excited me a few moments later, even if I was unwilling to admit it.
I finally let go of my cock and took her hardness into my hand alone. Valerie lay her head on my shoulder and said "Thank you." I stopped long enough to find some lubricant. I took her cock back into my hand and basically jerked her off. When she came, her long nails dug into my bare shoulders. She drove her tongue into my mouth as I felt the warmth of her orgasm raining down on my own cock below.
I took her anally, of course. I never had anal sex with a woman, that wasn't my thing. Obviously with Valerie that wasn't up for debate if I wanted to fuck her. I took her from behind and pushed my cock into her slowly. She cried out and I wasn't sure what to do. Suddenly I felt her hand around the base of my cock and Valerie guided me into her as she wanted me.
I fucked her hard, and she begged me not to stop fucking her. I only lasted a few minutes as my excitement was more than I could take. I came inside of Valerie within a few minutes, holding onto her shapely hips as I shot my load into her almost savagely. I didn't stop thrusting until the very last tingle of excitement had passed.
Valerie collapsed onto the bed and I collapsed on top of her a moment later. Both of us breathing hard as if we had run a marathon. She reached out and took my hand entwining our fingers as we lay there trying to calm down. At some point I got up and went to the bathroom to clean up. Standing in the shower my mind was trying to figure everything out at once, from the time I was 18yo until this very night.
When I came out of the shower Valerie was sound asleep, she lay on top of the covers still wearing her stockings and heels. I pulled off her heels and put a blanket over her, then went out back for a smoke. The sky was just starting to get light when I crawled into bed. Valerie put her arm around me and pulled herself against my back, I fell out about one minute later.
When I woke up later that morning Valerie was gone. I smelled coffee even before I got to the kitchen. She had made a pot of coffee before she left. There was a note from Valerie next to the coffee pot. "The best night of my life, I want more!" Love Val.....
We have been going together for over a year now. Have I gotten used to the fact Valerie has a cock, NO! What I have gotten used to is the fact she is a great human being and we have a lot of fun together outside of the bedroom too!
As I grew up and had relationships some of my girlfriends would indulge my fetishes, and even one of my two wives did as well. My wife passed away and I found myself back on the dating scene once again. Now finding a mature gal that likes the things I do is anything but easy. Most women in their 50's don't even want to get near a pair of high heels, much less wear them for the purposes of having sex.
After several months of dating women and not being satisfied sexually, I began to get desperate. I heard about the website called Craigslist. I knew it was a website people went to if they wanted to sell something, I never realized that people were also selling themselves on there as well.
I began to look through the postings, and hell I could even be direct and upfront what I was looking for. I didn't have to worry how I was going to tell the woman what I wanted sexually from her. It was either yes or no and then I would just move onto the next posting.
Of course the majority of the women were prostitutes and they would give me whatever I wanted for s rather premium price. I didn't want that, I wanted a relationship with a woman that would indulge my fetishes. Weeks and months went by until one night I got a response to my posting.
Her name was Valerie and she was about ten years younger than me. She included a picture with her wearing something very sexy and she told me she loved wearing those things because it made her feel sexy as well. So I emailed her back and told her I wanted a relationship, it wasn't just about the sex. She told me that's what she was looking for as well and we decided to meet.
We met the next week at a local bar that was about half way between her place and mine. Valerie was very pretty and had a nice body. She wore a rather snug fitting top that accented her large breasts, jeans and black knee boots over them. After our introduction we found a booth over in the corner of the bar to talk.
The booths were dimly lit with a candle glowing in the middle of the table. As we talked, there was just something about Valerie that wasn't right for some reason. She looked sexy as hell without a doubt, but something was off just a bit I couldn't figure out.
We had several drinks and a band rolled in about an hour later to play. We hung out, had a few more drinks and even danced a little bit which Valerie really enjoyed. She said her last boyfriend refused to dance with her. By 2am the bar was closing and we had to leave.
Standing between our cars, Valerie kissed me and put her hand on my crotch. We hadn't really planned anything about getting together as yet. Valerie whispered in my ear that she just happened to have an overnight bag in her car in case she was invited to my house. I let it be known she was definitely invited!
Valerie followed me to my house and after a brief make out session she asked to use the bathroom to freshen up. So I showed her where it was and a few minutes later I heard the shower running. I figured I would do the same while she was getting cleaned up, but first I lit some candles and killed the lights.
When I came out, Valerie was stretched out on the sofa. She had a glass of wine in her hand and had another glass sitting of the coffee table for me. It was hard to care about the wine when I saw how she was dressed. She had on this camisole that could barely contain her ample breasts, even in the dimly lit room I could see her nipples that protruded from behind the shiny material. She had on a matching pair of panties with stockings and a pair of black patent pumps on her feet. Frankly I could care less about the wine at this very moment.
We started to make out before the wine glasses were empty. The taste of her lipstick was on the tip of my tongue as the excitement began to build between my legs. I fondled her breasts and the tiny string holding the camisole closed somehow became undone. I began to kiss her breasts and nipples and saw the marks from her implant surgery underneath during my advances.
Valerie's hand found it's mark between my legs and with a bit of rubbing had me hard as steel. She coaxed me out of my jeans without much effort and I watched her painted lips slide down the length of my shaft. It had been a very long time since I had been with a woman, and to say I was ready would be an understatement.
We managed to make our way to the bedroom fairly quickly, Valerie was as aroused as I was by her actions. We made out some more, her tongue swirling around my mouth frantically, and I reciprocated as well. Her hand found my cock again and began to stroke me as we kissed.
I reached down, spreading her sexy legs and put my hand down into her panties a moment later. The first thing I would have noticed was she was shaved, but there was something else that felt different. There wasn't a opening I had expected to feel, it was a bump of some kind.
I sat up in bed and pulled her panties down slightly. The bedroom was dark but the street lights made enough light in the bedroom to see well enough. Valerie reached down and untucked her semi hard cock at this moment. There it was half erect in her hand, almost as big as my own cock. I sat in shock as she stroked it, wiggled it, as if to get the blood into it quicker. It became hard as my own in moments and Valerie moaned in pleasure jerking her own cock.
"Please don't stop now." Valerie sat up in bed and onto her knees next to me. She put her arms around my neck and kissed my face. I couldn't take my eyes off of her cock and it stuck straight out next to me. "Please don't reject me" she whispered into my ear.
I sat frozen in the darkness. What the hell had I done, what had I got myself into because of my fetish. "Please don't make me go," Valerie whispered. I wanted her to go, I was cursing myself in my mind for dealing with my own demons I didn't ever understand since I was a kid.
I reached out and brought my hand underneath her semi hard cock and lay it in the palm of my hand. Valerie wrapped her arm around my neck a bit more as we both tried to guess what my next move would be. "Please don't stop." Her voice was pleading, like a child that really wanted something she couldn't have.
Valerie told me to kneel up in bed and face her. She kissed me again, but my mind was trying to sort all of this out now. Suddenly I felt her hand around my cock as she continued to kiss me. At first there was no reaction. but the more she stroked it the blood found it's way and I began to get hard.
She kissed me harder and I began to get lost in the moment. Soon I was hard as steel again when I realized the warm sensation against my hardness. Valerie was holding her own cock as well as my own in her hand. She rubbed them together and stroked them in unison. I began to breathe faster just as she was as well. I couldn't bring myself to look, but I saw it in my mind. Her cock and mine clasped together in sexual lust, and I allowed her to keep going.
In the darkness Valerie took my hand and guided it to where hers was now. She took our cocks and guided them into my hand a moment later. My hand wrapped around our cocks and I squeezed us gently, Valerie kissed me again and moaned with pleasure. I reached down with my other hand and held our cocks even more tightly, Valerie started to move her hips with her hard cock within my grasp. The sensation against my cock excited me a few moments later, even if I was unwilling to admit it.
I finally let go of my cock and took her hardness into my hand alone. Valerie lay her head on my shoulder and said "Thank you." I stopped long enough to find some lubricant. I took her cock back into my hand and basically jerked her off. When she came, her long nails dug into my bare shoulders. She drove her tongue into my mouth as I felt the warmth of her orgasm raining down on my own cock below.
I took her anally, of course. I never had anal sex with a woman, that wasn't my thing. Obviously with Valerie that wasn't up for debate if I wanted to fuck her. I took her from behind and pushed my cock into her slowly. She cried out and I wasn't sure what to do. Suddenly I felt her hand around the base of my cock and Valerie guided me into her as she wanted me.
I fucked her hard, and she begged me not to stop fucking her. I only lasted a few minutes as my excitement was more than I could take. I came inside of Valerie within a few minutes, holding onto her shapely hips as I shot my load into her almost savagely. I didn't stop thrusting until the very last tingle of excitement had passed.
Valerie collapsed onto the bed and I collapsed on top of her a moment later. Both of us breathing hard as if we had run a marathon. She reached out and took my hand entwining our fingers as we lay there trying to calm down. At some point I got up and went to the bathroom to clean up. Standing in the shower my mind was trying to figure everything out at once, from the time I was 18yo until this very night.
When I came out of the shower Valerie was sound asleep, she lay on top of the covers still wearing her stockings and heels. I pulled off her heels and put a blanket over her, then went out back for a smoke. The sky was just starting to get light when I crawled into bed. Valerie put her arm around me and pulled herself against my back, I fell out about one minute later.
When I woke up later that morning Valerie was gone. I smelled coffee even before I got to the kitchen. She had made a pot of coffee before she left. There was a note from Valerie next to the coffee pot. "The best night of my life, I want more!" Love Val.....
We have been going together for over a year now. Have I gotten used to the fact Valerie has a cock, NO! What I have gotten used to is the fact she is a great human being and we have a lot of fun together outside of the bedroom too!
