Substitute wife
First off, I have been crossdressing forever. My name is Joe, I am short in stature..5'5" and 150 lbs wet. I have longer hair light brown (shoulder length) and green eyes. I have always had a preference for older, senior men, but I don't really push for it too far...if it comes, then it does.
I recently moved to a small town in the midwest to an established neighborhood with a pretty good sprinkle of retired people. I try to walk a couple of blocks every late afternoon for a little exercise. One afternoon as I was walking, I passed one of my male neighbors that was working in his front yard. The gentleman was tall and looked like he was in pretty good shape. I sprang out a "good afternoon" and he acknowledged with a wave. I continued on with my walk without a thought.
The next day as I was out for my walk, I passed by the same house and my neighbor again was in his front yard doing chores. I said " good afternoon" again and commented as to that is was such a nice day to be out. He said that it sure was and he walked over to the sidewalk were I was standing to further our conversation. A peculiar look came over his face as he approached, a look of surprise I would say, only for a moment, and then he kind of shook his head and outstretched his hand and introduced himself as Jim. I introduced myself and complimented Jim on what a good looking yard he had. He thanked me and said that he loved working in his yard and took pride in its appearance. I told him that I was fairly new to the neighborhood and enjoyed a walk in the afternoon. We made some more small talk and he mentioned that he was finishing up for the day and invited me to join him for a cold drink. I accepted and followed him into the house. His house was just as immaculate as his yard was, very well decorated and kept. I followed him into the kitchen and he asked what I preferred to drink. I said anything was fine and he said that he was going to have a have a whiskey and ginger. I said that sounded fine to me. He handed me my drink and suggested we sit on the back patio. His back yard was just as beautiful as the rest of his house and front yard with great looking landscaping and a in ground pool.
We sat on the patio and made some small talk. Jim said that he was a retired engineer and lived in the area for about 5 years. He and his wife moved to the location from the big city to get away from the crowds. But alas, she died unexpectedly 2 years ago, and he was left to fend for himself the last two years. I offered my condolences, and he lowered his head and swiped at his eyes. He said that she missed her every day and it was hard for him to talk about it. I said that it was understandable and apologized for bringing it up. Our drinks were empty and he asked if I wanted a refill, which I obliged him. I asked to use the bathroom and he said sure and to follow him he would show me were it was. He pointed out that the bathroom was down the hall to the left. As I was walking down the hall, a picture hanging on the wall was of Jim and his wife. I had to pause a minute and look at it again. His wife had a striking resemblance and I realized that she looked just like me.
After my bathroom break, I walked back to the kitchen and Jim was standing at the counter visibly sobbing. I asked him what was the matter and he asked If I happened to see the picture in the hall. I said yes I did notice it and he explained the look on his face when we met in the front yard, he was taken aback on how much I resembled his wife. I walked over to Jim and placed my hand on his forearm to console him. He reached his other hand around my back and embraced me. As he did, I could feel that he was getting hard. I broke the embrace and he apologized for the sign of affection. But he couldn't help himself. He missed his wife and he hadn't been intimate with anyone since she died. Now it was my turn to embrace him. I had to stand on my tip toes to intertwine my finger behind his neck as I hugged him. He slid his hands down and caressed my ass as we hugged. I reached my hand back around and slid it down to his crotch and gave it a rub and he let out a moan. I suggested that perhaps he should show me his bedroom.
As we went into the bedroom, Jim again embraced me and this time we kissed. His tongue worked its way into my mouth as his hand caressed my back, I broke the embrace and admitted to Jim that I liked to crossdress and perhaps he would like i if I went back down to my house and grabbed some things to wear to bed. A big smile came over his face as he led me over to the one closets. He opened it and it was full of his wife's clothes. He admitted that he could not throw them out, they meant way too much to him. I noticed a wide selection of nightgowns. On the floor was a selection of sexy bedroom slippers. He took me over to the dresser and opened the drawer to his wife's intimates. Bras, panties, stockings and garters. I asked if he had a favorite outfit that he liked and he shook his head yes as he reached in and grabbed a black brallet with matching panties. Then he found a black lace garter and silk stockings. He went back to the closet and grabbed a black teddie and 4 inch fuzzy mule slippers. I took all the items in hand and said that I would put them on in the bathroom. I gave him another hug and rubbed his crotch before I went in the bathroom..He was really hard.
In the bathroom, I slipped out of my boy clothes and put on the ensemble that he chose. They fit surprisingly well. I had been on hormones for awhile and my breasts fit the bra quite nicely. When finished, I looked at myself in the mirror. Everything appeared to fit fairly well, even the mules. I noticed another closet door off the medicine cabinet and opened it. It was filled with his wife's makeup, perfumes and such. I didn't want Jim to wait as I applied makeup so I just grabbed and atomizer and sprayed an ample amount of perfume up and down my body. The scent was sweet and flowery and light, not overbearing. I gave myself one last primp and opened the door to the bedroom.
As i entered the bedroom, I noticed that Jim was on the bed and had stripped down to his boxer shorts. He was obviously so hard that his cock was stretching the material to the max. I walked over to the foot of the bed and asked if he liked what he saw. The biggest smile was on his face.I mentioned that I would have applied some makeup but he said my wife really only wore it on special occasions when they went out, so the basic look was fine with him. I walked to the side and crawled in beside him and we embraced and kissed. He mentioned that the perfume was his favorite and really was a nice touch. My hand made its way down to his crotch and I opened the fly and his cock sprang out. His cock was not overtly large but was above normal size. I asked Jim if he wanted me to suck on him and he said that was really not necessary because he was quite hard and wanted to last. He told me that what he usually did was pleasure his wife first with his mouth to get her wet and then they would have intercourse. I told him to remember that I didn't have a vagina but I really like my boy pussy licked. I also told him that my cock was not very large, only about three and a half inches hard and he said that was perfect, his wife had an unusually large hooded clit and it would just be like pleasuring her. He reached down and rubbed my cock and proceeded to crawl between my legs. He ran his tongue all over my croth and I could feel my cock stirring. He reached his fingers in the band of my panties and slid them down my legs. Next, he grabbed my ankles and spread my legs and proceeded to lick my boy pussy. I let out a moan of pleasure as his tongue circled the opening and found its way inside. He moved his hands down to the back of my knees as he continued licking. I rested my legs on his shoulders and he reached up and started fondling my breasts and tweeking my nipples, which were super hard. His tongue moved over my ball sack and he sucked them gently into his mouth. He brought his hand down and started rubbing my cock which by now was pretty hard. His mouth moved to my cock and he gave it a lick and then swallowed the whole thing and started sucking. I let out another moan as he sucked my cock. I asked if he would slow down because at this rate, I wasn't going to be able to hold my cum. He went back down to my boy pussy and spread his saliva over the opening and then inserted his finger inside. The feeling for me was overwhelming and I told him I was ready to fuck. He moved up and spread my legs again as I placed my left leg on his shoulder and he guided the head of his cock to the opening of my boy pussy. He gently inserted it, slowly gliding it in me. he stopped while it was in a few inches and asked if he was hurting me. I said no he wasn't and to just take it slow like he was doing. He slowly glided it the rest of the way and started a slow in and out motion as he embraced and kissed me. The feeling for me was quite intense, I never felt so overwhelmed with a cock inside of me. By this time I was raking my finger nails down his back as he slowly fucked me. After a few minutes, he said that he was ready to cum and I said that I was also. His pace quickened as he lifted me with his arms around my legs and he let out a low gutteral moan and I could feel his hot cum shooting inside of me. I also let out a moan as my cock also started to erupt and shot all over my belly and chest. He let me back down and slumped his body weight on top of me as he slowly pulled his cock from inside of me. I could feel his warm cum oozing out of my boy pussy as he rolled off of me. I slid down between his legs and took his cock in my mouth and sucked the last drops from it as it softened. He also slid between my legs and licked the cum oozing from my boy pussy and moved up to my cock and took it into his mouth and sucked the final drops from it. He moved even further and licked some of the cum from my belly and then, moving even further up, kissed me and our combined juices mixed in a glorious cum kiss.
We laid there in each others arms and he thanked me for letting him pleasure me. I told him that the pleasure was all mine and if he was up to it, we could do it again. But he said that with age, it took him longer to reset. He also said there were some things that he needed to do and asked if he could get a rain check. I smiled and said anytime at all. We exchanged phone number and I changed out of the lingerie. He walked me to the door and we embraced again and he again thanked me for the sex. I told him I was always available for a repeat performance and we parted ways, until the next time.
