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Learning Something New About Myself

Learning Something New About Myself

by Lifelongsissy
6 min read
4.59 (8600 views)
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When I was 18 I knew a bit about my sexuality but like most I still had a lot to learn.

I loved crossdressing, sucking cock, cum and being fucked.

My best friend at the time lived with his Mother and Grandfather whom, we all knew had a thing for young guys.

He was just shy of 60 and still very virile and kinda sexy.

He was always flirting wirh our group of friends and frequently would use sexual innuendo whenever we were around.

My friend and his mom were going on a two week vacation to California and his mom told me I could use their pool anytime I'd like when they were gone.

So they left on a Friday so on Saturday knowing "Pops" (our knick name for his Grandfather) was home alone,I put my plan to seduce him in motion.

I made sure I was totally smooth and clean inside and out. Picked out a shiny bright blue 2 piece bikini with tiny bottoms.

I painted my toe nails bright pink. put on water proof eyeliner and mascara. Then put my long hair in a girly pony tail with pink hair ties.

I threw a towel,sun tan lotion,Vaseline and bright red lipstick in my bag and put a pair of sweat pants and an oversized tee shirt. With a pair of tennis shoes to hide my painted toes. And drove to my friends house.

When I parked out front I noticed Pop's car in the driveway, so I knew he was home. I walked around the house to the back patio by the pool deck.

Through the sliding glass doors I could see Pops sitting at the breakfast table with a coffee mug in his hand. I waved and he waved back.

As I was setting my bag on one of the lounge chairs he came outside and asked how i was. I told him i was "Fine" and I wanted to hang out by the pool and "maybe get some sun."

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He asked if I would mind if he hung out as well and I told him I'd like the company.

He asked "What's with the ponytail?" Then said "I've never seen your hair like this but I like it." and asked "Is that makeup on your eyes? "

I just smiled.And asked "Can you keep a secret?"

He answered "I keep lots of secrets."

So I asked if I could use the bathroom. He said "of course"

So I discreetly grabbed my lipstick and headed inside. In the bathroom I applied my lipstick and took off my shoes, sweats and shirt. And I headed back outside.

Pops was semi reclining in a lounge chair when I stepped out the door he stood up and asked "What the Fuck? "

I extended my hand and said "Hi Pops my name is Tara,nice to meet you." To my surprise he took my hand and kissed the back of it.

He said "Nice to meet you young lady." As I could see and feel his eyes all over me. So I twirled very slowly and asked if he liked my secret.Pops said he did indeed like it.

I told him I was going to take a dip. I walked slowly to the pool steps paying particular attention to keep one foot directly in line with the other so my walk was very feminine. I could feel his stare burning a hole in my bikini bottoms.

I knew I was teasing him big time and I loved how powerful it made me feel. I walked down the stairs and slipped in the water keeping my face above the water.

I swam a couple laps using a Breaststroke. I made my way out of the pool and took out my towel a gave Pops a closeup show, bending to dry my legs so he could really appreciate my ass. And by the way his shorts were tenting as I turned around, he must have appreciated it.

I ran my hands softly through his sexy salt and pepper hair and he let out a soft moan. So I leaned in and brought my lips to his and he offered me his tongue and I sucked it like it was a tiny cock running my tongue around it.

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When we were kissing I slipped my hand under his waist band and under his underwear and gripped his cock. It was about 7 inches long but very thick. It felt amazing in my hand as I slowly stroked it.

When we came up for air he said "Tara your being a very bad girl."

I whispered in his ear "That's the whole idea." and asked "Are you going to fuck me now?"

To that he pulled my hand from his shorts, stood up and put his hands on my hips from behind and guided me into the house towards his bedroom.

As we walked he said again that I was a "bad girl " and I felt a hard smack on my ass. As my suit was still wet it stung that much more. As painful as it was something weird happened. My little clitty got instantly hard as a rock. And i turned and smiled at Pops.

He took that as a sign that he was on the right track and when we reached his bed he sat down and pulled me face down over his lap.

Then I felt the second smack a bit harder than the first and that was followed by about 10 more then he switched to my other cheek for another 10. When he finally stopped I had tears streaming down my face but he removed my bikini bottom and discovered I had cum a ton in them.

He had me go look at my ass in the mirror and I was pleasantly surprised to see it was bright red, and it stung when I rubbed it.

He had removed his clothes and was lying on his back and his cock was beautiful and hard so i climbed between his legs and engulfed it with my mouth. I sucked his cock for about 5 minutes when he stopped me. He asked if i would like to ride his cock and I remembered I forgot to bring the Vaseline in when he leaned over and grabbed a bottle of lube out of the nightstand. I was so relieved to see that. He poured a generous amount on his cock and threw the bottle aside.

I climbed up and positioned my Boi-cunt on his cock head and started to lower my weight on it.

It rook some doing but the head finally popped in and it hurt like hell. I sat still for a few minutes while the pain subsided then I lowered myself down slowly until my ass was resting on his thighs. I started slowly rising up and lowering back down.

After a few minutes I started to ride his cock hard And I felt his hand smack the side of my ass and all I could do is yell "Please Pops Fuck me harder and hit me harder Please Pops.'

He Smacked me again and I shot cum all the way to his chin and all over his chest and belly. That triggered him and he drove his cock deep inside me and unloaded deep inside me.

I collapsed on top of him and kissed him and thanked him. He replied "We're just getting started you bad little girl."

We fucked two more times with a lot more spanking before I went home. As I drove home I realized that I just found something new that really turned me on. Apparently I really love being spanked.

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