Straight Male / 50
Lily and Tom were neighbors for many years, they were right there when my wife Joan passed away. We were like peas and carrots the four of us always doing something together even if going out to eat.
After Joan was gone I wasn't much into being the third wheel with Lily and Tom, mainly stay at home going out only when I had to. After a long while of mourning Joan I tried to move on with my life.
Lily tried to hook me up with a friend or two but I just wasn't into it. At some point I began to think about sex. Joan and I had a great sex life, she had a great collection of heels and bedroom outfits to wear for me. The idea of going to bed with a woman naked just never appealed to me no matter how horny I was. At some point I had to express that to Lily because she asked me why I didn't want to start dating someone else. I even told Lily that I couldn't bring myself to get rid of Joan's things, especially all of her heels and sexy night wear.
At some point Lily would come over to check on me and always the conversation turned to the things I told Lily about before. Frankly I was a bit embarrassed to tell that to her, I just didn't know she would keep bringing it up almost every time. It was like she was picking my brain for answers on why I liked those things so much? Finally I had to tell Lily one day not to bring it up anymore, it was embarrassing and a bit painful.
Lily reached into her purse and pulled out her phone and handed it to me. At first I wasn't sure who or what I was looking at. It was a picture of Tom and he was dressed up in women's clothing. Lily had taken a picture of Tom standing with a glass of wine in his hand. Tom was wearing a frilly white blouse, black skirt, stockings and heels. Tom was also wearing a dark semi curly wig and makeup. There was another picture of Lily and Tom seated on the Sofa with a glass of wine in their hands. Lily was wearing a rather skimpy bodysuit with stockings and heels, her breasts easily noticeable through the thin nylon material. All the years I we had known Tom and Lily I would have never suspected this from them. Hell I was shocked to see Lily wearing such high heels, she always wore flats or very low heels.
I just looked at Lily and then back to the picture on the phone until the screen went dark. I didn't know what to say to that. Lily took the phone and dropped it in her purse and asked me for a cup of coffee. For the next hour Lily laid it all out. Tom had been a cross dresser for years, she never dared tell anyone about it, not even her Mom when she was still alive.
Lily told me about a strapon she used on Tom, she would have sex with Tom dressed as a woman. I wanted to tell Lily I had heard enough but honestly I couldn't bring myself to, suddenly I wanted to know everything about what they did. I was shocked and for some reason excited that Lily would share this with me.
I asked Lily about Tom doing her? Lily said Tom didn't perform, his cock was in chastity all the time. I actually had to ask what she meant. Tom wore a metal cage around his cock, never to get hard and even peed through it daily. I couldn't help but ask Lily how she got hers so to speak. Tom would orally do her and use his fingers, that was about it. Lily went on to say they hadn't had normal sex in over Ten years. I think Lily realized she had told me things she didn't plan to, she got up quickly and left. I watched as she crossed the street to her house quickly, only looking back at my house before going inside her front door.
I didn't see much of Lily after that day, I'm sure she must have been embarrassed after sharing her secrets. For her being 50yo Lily was still attractive, obviously she didn't have the figure of a Twenty year old but she was still in pretty nice shape being on the petite side.
One night I was watching TV when the doorbell rang, it was almost 8pm and there wasn't many people out now during the work week. I answered the door to see Lily standing there all made up as if she were going out on the town. In fact Lily was over dressed wherever she was going to go. She wore a lot more makeup and her attire was rather on the alluring side. It didn't take me long to notice she was wearing high heels as well, the ones I had seen in the picture
I invited Lily in and she seemed to hesitate for a moment before stepping inside. We sat in the living room and I could see that Lily was nervous about something. I had the feeling that Lily was about two seconds from crying. I sat down next to her and asked what was the matter?
Lily looked at me for a moment and then kissed me dead on the lips. It was like a sudden shock to feel the softness of a woman's lips on mine once again, it had been almost two years since I had felt Joan's mouth on mine.
Lily and I made out like two kids in heat and soon I felt the stirring between my legs almost at once. My hands found the curves of Lily's breasts through the thin material of her blouse and I squeezed them gently. Lily made a sound that let me know it was okay and not to stop.
But suddenly my senses came back, Lily was married and should I be doing this with anyone this soon after Joan? I think Lily sensed what I was thinking and she pressed her body to mine so I wouldn't pull away from her.
We never made it off the sofa, we made love right there. I took Lily with her still mostly dressed except for her blouse, bra and panties removed. I went down on Lilly, pushing up her black skirt and feasted on her wetness. Lily dug those heels into my back the way the Joan used to do when I made her cum with my mouth. My cock throbbed underneath and I wanted to be inside of Lily now more than anything.
I broke the moment, telling Lily I had no Condoms. She suddenly looked up at me and said I didn't need one with her, it was almost as if she would have been disappointed if I had used a Condom with her. I tried to hold back, tried to make it last with her but I couldn't. It had been almost two years and I was desperate to have that feeling of release again. I came and the sensation of cumming was overwhelming.
I know I must have sounded like a wounded animal when I came. Lily's eyes were closed, she was cumming in her own way. Her nails dug into my back as I pumped my juices inside of her, I could feel her contractions around my hard cock as she climaxed.
Finally it was over, I lay partially on top of Lily. Her small breasts with her nipples hard as buttons. I wanted to savor them again and Lily allowed me to do so. My spent cock slipped out of her soon after and I struggled for the energy to get up off the sofa. I told Lily to use the guest bathroom I would go upstairs to use the other to clean up.
When I returned a short time later Lily was nowhere to be seen, the bathroom was empty and Lily was gone. I spent the rest of the evening looking over at her house, I wanted to call to make sure Lily was ok. Finally around midnight I went to bed, it was the best sleep I had in a very long time.
The following evening Lily was at my door again, she was dressed as she usual in flats and regular clothing. She started by saying not to be mad but she had to get home to Tom. Then she told me other things after we sat down.
The reason she had to get home was the fact that Tom was waiting for her. Now the rush of guilt came over me because I had fucked my best friend's wife. Then Lily dropped the bomb on me. She told me that Tom knew we had sex, that's why she came over last night. I asked Lily to say that again as if I hadn't heard her correctly. She repeated that Tom wanted Lily to have sex with me, but there was more to the story.
Tom wanted my cum, that's why Lily rushed home the way she did. Lily explained that Tom had been wanting a cukhold relationship for years to go along with his cross dressing fetish. So Lily told me when she got home Tom was all dressed up waiting for her in the bedroom. Lily would get on the bed and spread her legs for Tom and he would take my cum out of his wife with his mouth. Lily could barely look at me now after telling me everything. I asked how she felt about Tom being a cross dresser and a cuckhold. She told me honestly it was hard for her to understand but she loved him dearly.
Lily dropped the second bomb. She wanted to know if I would be willing to have sex again with her sometime? She told me she had her own motives as well because she needed sex with a man that could satisfy her sexually. I asked Lily if she would do the same thing after we had sex and take my cum back to Tom? She couldn't look me in the eye when she said yes.
Lily and I have been having sex for a few months now, each time she takes my cum and leaves soon after we are done. I love having sex with Lily and having her all dressed up for me is exciting once again. The idea of her leaving right after doesn't sit well with me, maybe it's because I'm starting to have feelings for her besides the sex.
Now there is something else. Tom wants to know if Lily and I can have sex at their house with Tom watching. I have two thoughts on this, one being no the other hell no! After Lily told me about Tom I began to check Online about his Fetish. So the next thing he will be wanting to suck my cum out of Lily's pussy he will want to be sucking the cum right from my cock. Sorry no can do!
After Joan was gone I wasn't much into being the third wheel with Lily and Tom, mainly stay at home going out only when I had to. After a long while of mourning Joan I tried to move on with my life.
Lily tried to hook me up with a friend or two but I just wasn't into it. At some point I began to think about sex. Joan and I had a great sex life, she had a great collection of heels and bedroom outfits to wear for me. The idea of going to bed with a woman naked just never appealed to me no matter how horny I was. At some point I had to express that to Lily because she asked me why I didn't want to start dating someone else. I even told Lily that I couldn't bring myself to get rid of Joan's things, especially all of her heels and sexy night wear.
At some point Lily would come over to check on me and always the conversation turned to the things I told Lily about before. Frankly I was a bit embarrassed to tell that to her, I just didn't know she would keep bringing it up almost every time. It was like she was picking my brain for answers on why I liked those things so much? Finally I had to tell Lily one day not to bring it up anymore, it was embarrassing and a bit painful.
Lily reached into her purse and pulled out her phone and handed it to me. At first I wasn't sure who or what I was looking at. It was a picture of Tom and he was dressed up in women's clothing. Lily had taken a picture of Tom standing with a glass of wine in his hand. Tom was wearing a frilly white blouse, black skirt, stockings and heels. Tom was also wearing a dark semi curly wig and makeup. There was another picture of Lily and Tom seated on the Sofa with a glass of wine in their hands. Lily was wearing a rather skimpy bodysuit with stockings and heels, her breasts easily noticeable through the thin nylon material. All the years I we had known Tom and Lily I would have never suspected this from them. Hell I was shocked to see Lily wearing such high heels, she always wore flats or very low heels.
I just looked at Lily and then back to the picture on the phone until the screen went dark. I didn't know what to say to that. Lily took the phone and dropped it in her purse and asked me for a cup of coffee. For the next hour Lily laid it all out. Tom had been a cross dresser for years, she never dared tell anyone about it, not even her Mom when she was still alive.
Lily told me about a strapon she used on Tom, she would have sex with Tom dressed as a woman. I wanted to tell Lily I had heard enough but honestly I couldn't bring myself to, suddenly I wanted to know everything about what they did. I was shocked and for some reason excited that Lily would share this with me.
I asked Lily about Tom doing her? Lily said Tom didn't perform, his cock was in chastity all the time. I actually had to ask what she meant. Tom wore a metal cage around his cock, never to get hard and even peed through it daily. I couldn't help but ask Lily how she got hers so to speak. Tom would orally do her and use his fingers, that was about it. Lily went on to say they hadn't had normal sex in over Ten years. I think Lily realized she had told me things she didn't plan to, she got up quickly and left. I watched as she crossed the street to her house quickly, only looking back at my house before going inside her front door.
I didn't see much of Lily after that day, I'm sure she must have been embarrassed after sharing her secrets. For her being 50yo Lily was still attractive, obviously she didn't have the figure of a Twenty year old but she was still in pretty nice shape being on the petite side.
One night I was watching TV when the doorbell rang, it was almost 8pm and there wasn't many people out now during the work week. I answered the door to see Lily standing there all made up as if she were going out on the town. In fact Lily was over dressed wherever she was going to go. She wore a lot more makeup and her attire was rather on the alluring side. It didn't take me long to notice she was wearing high heels as well, the ones I had seen in the picture
I invited Lily in and she seemed to hesitate for a moment before stepping inside. We sat in the living room and I could see that Lily was nervous about something. I had the feeling that Lily was about two seconds from crying. I sat down next to her and asked what was the matter?
Lily looked at me for a moment and then kissed me dead on the lips. It was like a sudden shock to feel the softness of a woman's lips on mine once again, it had been almost two years since I had felt Joan's mouth on mine.
Lily and I made out like two kids in heat and soon I felt the stirring between my legs almost at once. My hands found the curves of Lily's breasts through the thin material of her blouse and I squeezed them gently. Lily made a sound that let me know it was okay and not to stop.
But suddenly my senses came back, Lily was married and should I be doing this with anyone this soon after Joan? I think Lily sensed what I was thinking and she pressed her body to mine so I wouldn't pull away from her.
We never made it off the sofa, we made love right there. I took Lily with her still mostly dressed except for her blouse, bra and panties removed. I went down on Lilly, pushing up her black skirt and feasted on her wetness. Lily dug those heels into my back the way the Joan used to do when I made her cum with my mouth. My cock throbbed underneath and I wanted to be inside of Lily now more than anything.
I broke the moment, telling Lily I had no Condoms. She suddenly looked up at me and said I didn't need one with her, it was almost as if she would have been disappointed if I had used a Condom with her. I tried to hold back, tried to make it last with her but I couldn't. It had been almost two years and I was desperate to have that feeling of release again. I came and the sensation of cumming was overwhelming.
I know I must have sounded like a wounded animal when I came. Lily's eyes were closed, she was cumming in her own way. Her nails dug into my back as I pumped my juices inside of her, I could feel her contractions around my hard cock as she climaxed.
Finally it was over, I lay partially on top of Lily. Her small breasts with her nipples hard as buttons. I wanted to savor them again and Lily allowed me to do so. My spent cock slipped out of her soon after and I struggled for the energy to get up off the sofa. I told Lily to use the guest bathroom I would go upstairs to use the other to clean up.
When I returned a short time later Lily was nowhere to be seen, the bathroom was empty and Lily was gone. I spent the rest of the evening looking over at her house, I wanted to call to make sure Lily was ok. Finally around midnight I went to bed, it was the best sleep I had in a very long time.
The following evening Lily was at my door again, she was dressed as she usual in flats and regular clothing. She started by saying not to be mad but she had to get home to Tom. Then she told me other things after we sat down.
The reason she had to get home was the fact that Tom was waiting for her. Now the rush of guilt came over me because I had fucked my best friend's wife. Then Lily dropped the bomb on me. She told me that Tom knew we had sex, that's why she came over last night. I asked Lily to say that again as if I hadn't heard her correctly. She repeated that Tom wanted Lily to have sex with me, but there was more to the story.
Tom wanted my cum, that's why Lily rushed home the way she did. Lily explained that Tom had been wanting a cukhold relationship for years to go along with his cross dressing fetish. So Lily told me when she got home Tom was all dressed up waiting for her in the bedroom. Lily would get on the bed and spread her legs for Tom and he would take my cum out of his wife with his mouth. Lily could barely look at me now after telling me everything. I asked how she felt about Tom being a cross dresser and a cuckhold. She told me honestly it was hard for her to understand but she loved him dearly.
Lily dropped the second bomb. She wanted to know if I would be willing to have sex again with her sometime? She told me she had her own motives as well because she needed sex with a man that could satisfy her sexually. I asked Lily if she would do the same thing after we had sex and take my cum back to Tom? She couldn't look me in the eye when she said yes.
Lily and I have been having sex for a few months now, each time she takes my cum and leaves soon after we are done. I love having sex with Lily and having her all dressed up for me is exciting once again. The idea of her leaving right after doesn't sit well with me, maybe it's because I'm starting to have feelings for her besides the sex.
Now there is something else. Tom wants to know if Lily and I can have sex at their house with Tom watching. I have two thoughts on this, one being no the other hell no! After Lily told me about Tom I began to check Online about his Fetish. So the next thing he will be wanting to suck my cum out of Lily's pussy he will want to be sucking the cum right from my cock. Sorry no can do!
