My Neighbor's "Daughter"

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My first time with a young cross-dresser.
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This happen to me when I was 40 years old about 10 years ago. It's after this I started to Cross dress.

About 6 years ago, after the passing of my wife, I moved in neighborhood closer to work. What I liked about this neighborhood is that the vegetation his well established and its private, nice and quiet. When I moved in you get to meet your neighbor, being a "don't mingle kind of guy", I wasn't thrill about it, but good neighbors are good to watch over the house when you are away or on vacation. At the time, they had a 15 years son, good kid, work hard, polite, good grades etc. He would mow my lawn occasionally when I was out of town. I do travel on business quite frequently and would ask him to keep an eye on it. Over the years, I remained single the thought of having another significant lover never appealed to me. I saw him aged, he didn't very much grow up, 5'4" maybe 125 pounds.

The years went by and he started college, he would come back during summer breaks. Last March he turned 21. I took upon myself to give him a gift card to the local mall for his birthday. Last June, his parents took a month-long vacation in Colombia to visit their relatives. The son stayed to watch over their house. I live in a 2-story house and my office is adjacent to their backyard which happens to have a Jacuzzi. One night I was working, and I didn't turn the light on, was just working on my laptop. A light from outside the window caught my eyes, it was the neighbors' Jacuzzi light. I was about to go pull the blinds down, as I do not want to be known as peeping tom. This when I saw him get into the Jacuzzi in a bikini, that intrigued me. I shut down my laptop and became peeping Tom. He was relaxing, started to rub his hairless body, pretending having boobs and he slowly start playing with is penis, but clit was more appropriate, that didn't grow much either as he aged. I started to enjoy the show, I had a few gay cross-dresser fantasies in my life, but I never saw them through.

At one point, he stood up and came. I was really turn on by then. That remained like this for the night, I wank and came. A couple of night after that welcome interlude from working. Again, being a workaholic, the patio light came on, I was hoping for another Jacuzzi scene. Close down the lid of the laptop and prepared for peeping tom evening. He stepped on patio. I should say "she" fully dress in a nice summer dress, wigs, make up, tan stocking, fake breast and high heels and sat down on the Adirondack chair with a glass of wine. I was really turn on, I grabbed my crotch and rubbed myself while he/she was rubbing her legs then my cock was urging to come out of my shorts. After a few minutes of stroking my cock watching him rub himself I decided to grab a beer and go outside. I made sure not to make noise and walk toward "her" backyard. He was rubbing himself and rubbing her clit through a pink pantie, you could see a dark spot of precum on them. This when I made my move.

"Good evening Miss, nice evening isn't it?"

"shit, Mr Logan, uh, uh, it's not what you think.

I quickly reassured her, "its okay sweetie, we all have the right to be who we want be, "gorgeous". May I join you, precious?"

After a moment of hesitation, she decided to play the game, she pitched her tone higher and said "please, I would love some company."

We chatted a little about her newfound fetish and admitted that she's been doing this for 4 years, but never had the courage of doing what she's doing until tonight. I told her that I'm glad she did, because she was gorgeous, and she has turned me on. She went to get herself another glass of wine and when she came back, she set her glass on the table and as she was about to sit down, I grab her wrist and pull her toward me and ended sitting in my lap. Her lips were luscious and inviting, I started to kiss her, she resisted a little and I forced her just a little. As I pushed my tongue in her mouth, the resistance stopped, and she started to reciprocate. She tasted delicious. As we were passionately kissing, I started to rub her stocking legs and my cock started to poke her, she looked at me and blushed, that's when I knew that she was mine for the taking.

We had a long hour of foreplay, by then I my shorts were soaked and so were her panties. If you are familiar with Adirondack chairs the armrest are high, raise her and sat her nice firm butt on the armrest, I was gently rubbing his leg and went up to her clit, rubbing it on the outside of the panties. I slowly, released it front entrapment and the most beautiful 3 inches clit came out, full of pre-cum. I kept rubbing it gently while she was deep French kissing me. I slow moved forward and started to lick her clit, twisting my tongue around it, I could feel her moan and her tight body tense here and there. I finally close my mouth on it and start to suck her clit. You must remember that this was my first too. Without warning, I felt her tense and she skirt in my mouth. That was a wonderful tasty experience. I swallowed every bit of it.

After I thoroughly cleaned up her clit with my tongue, she looked at me embarrassed that she came so quickly, I winked at her and lower her down on my lap and French kissed her more with cum still in my mouth. I stood up with her in my arms and proceeded to my house in my bedroom. I threw her on my bed, I got undress and my cock, which is not the biggest in the world (6.5 inches with a good girth) was fully erect. She again blushed, before I could laydown beside, she move to the edge of the bed sat down and started to suck on my cock, like a real cock sucker, she took it all in, suddenly she was sucking at it like pro, she was grabbing my balls with a few gentle squeeze and also was rubbing that area between my ball and anus occasionally pressing in the area. This had the desired effect, I grad her head to make sure she would wouldn't pull back and let my load go down her throat. After, a few deep thrusts, I let pull back and I kissed her more.

I grab her and threw back on the bed and I lay down beside her and we did more foreplay. It surprisingly did take a us a long time to get hard and ready for more. As we were kissing, I started to rub her pussy, thankfully I had lube in my nightstand, for my occasional wanking. Again, I was rubbing her pussy gently on the outside and could see her clit throbbing and oozing of pre-cum. I gently start pushing my middle finger in and she tensed so hard that I thought she would break my finger, I told her I won't hurt you and we'll go slow. The more I rubbed and the more it went back and forth she started to moan and decided that I would lube my cock and break in a virgin ass. At first, I could tell she was a little terrified, I told her not to worry. I slowly started with the head of my cock, she was tight, I kissed her more, she relaxed and this when I rammed it in. My god, that was so tight and explosion sensation came all over my cock. She grabs by the neck and kissed me really hard. But at the same time, she was trying to push me away.

I grabbed her legs over my shoulders and then pressed down her arms against each side of body so she couldn't move. I started to thrust in and out and she trying to break free, but my 6', 185 lbs body was no match for her 125. As I'm fucking her, I lower down myself to kiss her more she started to grab my ass for me to go faster, I went faster she screamed and came so hard and her anus contracted to hard that it made me come too all that while kissing. After few grunts, a fell beside her and she cuddle with me. This was by far the best sex I had ever had in my life. We fell asleep and woke up the next morning.

There is more, but that is to be continued...

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9 Comments
kriss4912kriss4912over 2 years ago

Great read do so hope there is more as think Mr Logan has found a truly lovely daughter and girlfriend

AnonymousAnonymousabout 3 years ago

I'm a crossdresser and I've been caught by my ex wife years ago. She had gone grocery shopping and I thought that I had a couple of hours to indulge in my crossdressing. I was in the process of getting dressed when I heard her calling my name. She had returned to get her coupons and when I wasn't in the living room watching television she wondered where I was?

She was coming up the stairs and I was frozen in my tracks wearing a pair of pink bikini panties and a matching bra, with a blonde wig and a pair of suntan stockings.

When she opened the door and saw me standing there she was shocked in disbelief

What the fuck are you doing she asked me?

Who's clothes are you wearing.?

Do you have a girl in our bedroom?

I told her that there wasn't any girl in our bedroom other than me

I told her that I was a crossdresser and I couldn't stop being a crossdresser

Her expression changed and she stood there looking at me

She said

I've always wanted to be with a girl. Will you seduce me as a girl?

I told her to let me finish getting dressed and I will.

She told me that I could and left me alone to finish getting ready.

I did everything getting dressed. Full makeup and a stylish skirt and blouse with a jacket that matched my skirt.

High heels and I told her that I was really.

She came back into the bedroom and looked at me

She told me that I looked beautiful and sexy.

I held my arms out and she came to me and I wrapped my arms around her and kissed her.

Her breathing got quicker and she said that she wanted to be with a girl for as long as she could remember.

We had incredible sex and she used a strapon that I didn't know she had on my ass. I was the girl who she seduced and it was the best sex I ever had.

She called me her cunt and I agreed with her.

After that, whenever we had sex it usually ended with me taking the strapon dildo up my ass.

She absolutely loved fucking me with it pretending that she was the dominant one in our marriage and I loved being the girl in our marriage

AnonymousAnonymousover 3 years ago
Ended differently

I am a smaller crossdresser at 5’4” and weighing around 140lbs and used to dress every chance I could. Only once did a neighbor catch me and he briefly mistook me for my mom. He never mentioned or came over again. Too bad my story didn’t turn out like yours!

AnonymousAnonymousabout 4 years ago
MORE

My imagination is swirling remembering my first time having my neighbor finding his Sissy next door all dressed and no were to cum/go

zazrix9zazrix9over 4 years ago
The only

Xdressing I like is shoes, high heels make me so horney I could fuck a rock, don't know how women get through the day with them on without at least seven different sex partners, and full of the nectar, Butt if X-dressing would make it easier to score huge fat gorgeous cocks in my holes, I'd do it.

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