Guilt and Embarrassment Meet Hormones - Uncle Robert

Hopefully you have read my introduction to how I finally got to live out what goes on in my mind. For most of my life I have always felt out of place, wanting to live up to being one of the guys but being short and thin, with long dark hair and blue eyes, it didn’t help. I seem to always be mistaken for a girl but it took me several years to grow into what I had been cursed or blessed with.

Because I was born into a trainwreck family, I was sent to live with my great uncle. He lived in a small 2 bedroom older mobile home but was gracious enough to let me move in. I was then 18 but moved in two years prior. Robert was married but divorced and had never remarried. Very much a bachelor at his age and happy.

As you can read, my femininity finally surfaced and I was caught. This eventually led to a million questions, some drinking and a night where both Robert and I gave into the tension of me being attracted to masculinity and me dressed like a slut, even though I thought what I wore was just sexy.

I had given him an awkward blowjob, snuggled with him later in bed and let him fuck me in the dark. Weeks passed and we barely spoke of it but one night while dressed and trying to get his attention once more, he took me to tease one of his friends. All I did was ask for directions but somehow this was exciting to Robert, like he had something on his friend now. We arrived back home and this is where this story begins.

We came back home and sat and talked about what Charlie’s face did when he looked at me. He said he knew his friend well and knew he had a thing for brunettes and even though he was 64, he always talked about younger women being sexy. I have to admit it was kind of erotic being used like that. After drinking several beers together, and a few shots, I asked him if that was a turn on to him.

After first denying it, he finally admitted that knowing his friend probably about came in his pants when I showed up, it was exciting. Sitting on the coach across from him, I slowly started positioning myself where the top of my stocking was visible. He got up to go pee and I asked jokingly if he needed any help shaking. Not sure what had come over me but flirting seem to come easy with him. And the taboo and privacy of it all was intoxicating. He didn’t seem to be flirting back much so I figured I could at least have fun.

I excused myself and went to freshen my makeup and made sure my lips were painted and very glossy. When I arrived back to the living room he had already poured several more shots for us both. Out of the blue he asked about the first time a man had ever flirted to me. I told him of a time at a local store while getting a drink out of a machine and I was wearing shorts. Never had much hair on my legs. But when I bent down I heard a man pumping gas say to his friend “damn, look at that ass” both were looking when I looked back. I explained that from that day on it wrecked me to think they found me hot enough to look. That was the beginning.

He asked why older men, I explained that it was a daddy thing I guess. That older men represented safety and masculinity. I explained my earliest fantasies dealt with being caught dressed by older men. Kinda like he did. Seeing his face when he said the next comment floored me, he said “ but why me that night? I am old and out of shape and your uncle”. I told him the taboo of it was very hot. We started talking about that no one could ever know and I assured him that I wasn’t about to tell anyone.

By this time we were both very drunk. I was trying to hold my cool but was getting more flirty. When he asked what I liked about sucking a man off I knew I was getting somewhere finally, a few questions later and me explaining that a man’s cock fascinated me and that I just like to see them, he stood and unzipped his pants. He said “fine I will let you look but not sure I can do what we did again”. He sat back down with his cock out of his pants just laying there. Now was my chance to see if he reacted.

When I got up to get us both another beer, I let my dress ride up my ass and I walked to the kitchen like that. When I came back I opened his beer and bent down in front of him to make sure he could see my bra. I could see a little twitch. I moved to the couch near him and joked that if he ead gonna have it out I could at least be closer to see it. I sat facing him and started asking about what he found sexy. We talked about things he had done and my inexperience. I asked him “ wouldn’t most men like to have someone who loved to suck cock and be fucked daily?” He agreed that was every man’s dream and as we talked I noticed him getting harder. I started to pour it on thicker.

In my most seductive voice I started asking about fantasies. I asked about if men like to cum on women’s faces, asses, mouths or anywhere. Harder now. Asked if men liked to fuck a woman anally, again much harder. Inching my way toward him the whole time. A foot or so from him, he noticed me staring closely at the drop of precum forming. What happened next started it all again. I took my finger and wiped his cock and put my finger in my mouth. Without a word I reached out and wrapped my hand around him. I started stroking him hoping he wouldn’t say no. Convinced he would I leaned down quickly and took him all the way into my mouth.

I started slurping like a porn star. All I could hear are moans. I went to my knees beside him with my ass in the air. Bobbing my head as fast as I could go. I felt his arm move and his hand immediately found my ass cheek. He started rubbing and found the crack and started pressing against my hole. I reached back and moved my panties out of the way. I grabbed his hand and brought it to my mouth and sucked two of his fingers giving him the hint.

Taking my cue he worked one then two inside me and started working my ass good. His cock was Rick hard and I didn’t k ow how long he would last. Bartering with myself if I wanted his cum in my mouth or my ass, I looked up at him and whispered “please fuck me” . He nodded. I felt his hands guide me onto his lap and I did the rest. Facing him I reached back and guided his cock into me. Slowly I lowered myself until I was sitting on his legs. The feeling was amazing, being stretched and full.

I started riding him and staring at him as I moved. Just the friction and the moment, not sure what came over me but I leaned in and kissed his lips. He looked a little shocked at first but responded gently. As our lips pressed together I instinctively started opening them and his tongue found its way to mine. I was in heaven with a cock deep inside of me and a masculine man kissing me.

I rode him for another 5 minutes or so when he said let’s go to the bed. We make our way to his bed and he stands me up and moves in behind me. He lowers me down a bit and started pressing into me. I felt him slide easily into me . His hands on my hips he started aggressively pounding me. I could feel his cock hit places in me that were making my knees weak. For a moment I thought he was fine but I started pushing back into him just as hard. He took the cue and pushed me on the bed hard. He pulled my hips up into a doggie position and started forcefully fucking me. All I could feel was the pressure in my abdomen every time he pushed hard. Finally I felt him tense up and flood my ass with cum. So warm and so much. Both of us breathing hard I held him inside me.

We laid there for a few minutes catching out breathe and the he said “come on, let’s go get another drink”. With his cum still leaking out I walked into the kitchen grabbed a beer for each of us and a shot. I sat down close beside him, his cock still semi hard. My hand rested on top.

That night we came to the conclusion that two people can have fun together. It’s just sex. It’s fun. We fucked again that night and I finally got to have his cum fill my mouth. I knew I was addicted that night. The next few months proved to be more than
I had hoped for.

Totally true story, can’t wait to share more.

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