Nextdoor Fantasy

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Transgender & Crossdresser, Gay Male.
1.7k words
3.99
8.7k
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This is pure fantasy on my part, but would love it if it came true!

Neighbor owner died a few months ago, she was a sweet lady 9 years older than I but in very decent shape for 80 plus years. Her son for the most part is sort of crazy and not one I would trust with my secrets. But on this day as the wife and I were loading the car with her bags she was taking for her visit to her relative in another state, he came out and was observing us. The wife left and as I was getting ready to go inside, he asked how things were going, and I said great, how about you since your mother passed. He said it was hard to deal with but was trying to get along.

I said I missed seeing her especially in the good weather when she would come out with her silky lounge wear on, she always looked so comfortable in them. He said yes she always loved to wear them outside as she could feel the air swirl against her legs. I laughed and said that must have felt wonderful.

He looked at me and said that her lounger robes were in the house would I like to see them, I said of course if he did not mind. He said come on in and you can check them out, so I had to lock my house first and he said ok. I came in and got my keys, went out the back door and locked it. Went over to their back door and he opened it as I stepped up onto the back porch. Went in and followed him to his mother's bedroom where I had been before as I had keys to the house, and when they were gone I had checked out her room.

We got into the bedroom and he opened the closet door and there was her lounge robes hanging there. I felt my cock stir in my panties just looking at them. He said if I wanted I could take them out to see, I stepped closer and noticed she had long and short sleeves gowns, I asked if I could arrange them and he said yes. I took them and moved the short sleeved ones to the right and the long sleeved ones to the right. Two caught my eye as they both had purple and lilac colors. I told him I thought they were the prettiest of them all, and he said I could try them on if I wanted too.

He knew from before that I liked feminine clothes, as he caught me dressed when I had first moved into my house. He never said anything about that but I knew. Anyway I asked here? He said yes, he wanted to see me feel the wind on my legs like what I had said about his mother. My little ole heart was beating faster and my cock was certainly moving around in my panties. I asked where, he said right here, just take off your things and put one on. Oh be still my heart, I so wanted to slip one over my head and feel that silky material fall down over my body.

I took off my hooded sweat shirt, laid it on the bed, pulled my golf shirt off over my head, when he asked if I would also wear his mother's slippers, I said that they probably would not fit, but he took them out of the closet and placed them down in front of me. I slipped my feet out of the sketchers I was wearing and slid my foot into the left slipper and it actually fit. He noticed that I had hose on and asked about that. I told him I wear support hose to help keep the swelling down in my legs. I slipped the right one on and smiled.

Then I took off my tee shirt laid it down on top of the golf shirt. Reached down and removed my gun from its holster and put it on the tee shirt, along with my cell phone. Unbuckled my belt and dropped my jeans, heard him draw in a deep breath, he noticed I was wearing silky panties. He asked if I always wore them I said yes. I took her lounge robe in lilac and slid it over my head, that felt so wonderful as the cool silky material slid down.

He said I looked nice and how did I feel, I told him I felt really good. He asked if he could give me a hug so he could feel me. I said yes and he stepped closer and took me into a hug embrace and his hands were on my upper and lower back. That felt so good, then his hands both dropped and he held both cheeks of my butt.

After a short time he backed away and asked if I would follow him to his bedroom, I said ok and he led off. By this time my cock was harder than it has been in quite a long time, and I could feel a wet spot forming. On entering his room I noticed his computer screen had a frozen picture of three guys, one in a doggy position and one behind him with his cock in his ass, the other guy had his cock in his mouth.

I said that is quite a picture, he laughed and hit continue and they did too, my cock was really getting pre cum all over my panties now. He said he was watching this when he heard us packing the car. Watching the screen was really getting me excited and also he was rubbing his crotch and looking at me. He asked if it would be ok if he took off his pants as it was getting tight in there.

I said it is your house now do what you need to do. He unbuckled his belt and dropped his jeans and sort of nice he had silky panties on too. Sure had a tent in it and so did mine, he asked then if I had ever been with another man, I said yes of course, would we like to pleasure each other, he said oh yes please it has been awhile since he has had a chance for it. I said the same with me. He stepped closer and took my cock in hand with my panties and the lounge robe covering me. I reached down and took his larger cock in my hands within his panties. We sort of held each other for a bit then he asked if I would suck him off. I said yes I would love to do that and knelt down while pulling a pillow off his bed to put my knees on.

I held his cock covered in his silky panties and leaned in and took it into my mouth, he let out a grown as he slid into me. Sucked for a short time then pulled back and dropped his panties and took his now naked cock into my mouth, it has been many years since I have had this pleasure of a cock in my mouth. He was close to being too long to deep throat but I managed to get him all in. It did not take long when I felt his cock enlarge a bit and felt his head get bigger and then felt his wonderful cum shoot into my mouth. That was such a nice feeling, the spurts of cum filling my mouth, the taste so good. I had to swallow and let him pulse a few more loads into me, I savored the texture and taste before I swallowed this load.

I finally pulled back and let his cock slip out of my mouth, his balls felt nice in my soft warm hands. He stood up and had a silly smile on his face, he said your turn let me suck you I said from the feel of my panties I may have already shot my load but you are welcome to try. He squatted down and let me lay back, he raised the gown up and pulled my panties down, then put his head underneath the material of the lounger robe and took my cock in his mouth, it felt so good and after a short time I did manage a small ejaculation of cum to shoot out.

He stood back up and licked his lips, and I noticed his cock was very hard and throbbing and I said looks like you need more. He said it would be very nice if he could fuck me, if I would like that. I said oh yes I would love to feel you inside me. He had a bench of sorts against the wall, he slid it over to the bed and told me to lie across the bench and pull the pillows up to me for comfort. He pushed the bottom of the gown up past my hips spread my legs open, leaned down and put the head of his cock on my hole. Having done this before I pushed down like taking a shit as he pushed in, His cock head slipped past the sphincter and he stopped, I said ok more please, he pushed and so did I and soon he was all in, oh how good that felt. He started slowly to fuck me getting faster and faster till he rammed in deep and I felt his hot cum shoot inside of me. It felt so good at this time it is hard to explain how nice it is to give pleasure while receiving it at the same time.

When he pulled out I sat up and licked his cock clean, he finally asked if I liked it and I said of course. Would I be open to coming back for another visit? I said yes, when the wife is gone and we are both ready. He laughed and said I am ready now, funny but his cock was hard again. I asked him if he would let me suck him again and he said yes, his load that time was smaller but still tasty.

I hope to continue this story if I get this one to go.

Deborah Anne

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AnonymousAnonymousabout 1 year ago

HOT arousing story I wish I was there!! Thank you!

woodseaveswoodseavesover 1 year ago

A lovely story, it presses a lot of buttons. I wish it could be happening to me

AnonymousAnonymousover 2 years ago

Forgot my contact naughtyhotcd6969 at proton mail dot com

AnonymousAnonymousover 2 years ago

Sooo lucky! I am a deeply closeted sissy crossdresser, been dressing since my cousin dressed me when she babysat me! Then my moms silky, full fashion gear, then my wifes sexy lingerie (that I bought for her, hahahaha!) Now that I am retired and she has lost her sex drive, she has thrown it all away. No problem, the thrift stores keep me sluttier than ever for cheap! Heels, corsets, garter belts, bras, thongs, hose from Target! Some cocks from doublelist but those are few and far between, sadly. I'd love to correspond and exchange pics and fantasies.

AnonymousAnonymousover 2 years ago

So hot and arousing!! You made me hard! I want to participate!!

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