Itsjayjayposts - Single Man

Someone cum on my soles😩

He’s my little brother. In the first picture I was 15 and he was 13, on the second one I was 17 and he was 15 and that’s when we started to have sex. The third picture is from a year later and the 2 last pictures are from this year, me being 20-21 and him 18-19.

Now I’m going to tell you the story about how my little brother and I started to have sex together.

It was summer and I already have has sex with my dad and my big brother and I wanted to have sex now with my lil bro so I just planned it.

It was my 17 birthday and I wanted to travel with my friends to the beach. I don’t know how parents are on other countries but here when you’re 17 you’re still a baby for your parents and they would never let me travel alone (I mean without them) buuuuut as I had sex with the man of the house, my father, he usually let me do whatever I want. So I told them my brothers were invited so maybe they could be cooler about me traveling hundreds of miles to the beach with a bunch of teenagers. The thing was (and I already knew it) that my big brother wouldn’t go because college. So it would be just my lil bro and I (and my friends).

We got some rooms at a hotel not so near to the beach to economize and save money for alcohol (and food why not, just some cans of tuna) lol. My brother and I got one single room with two beds and my friends took other rooms that was a waste of money because that was a party that lasted all day and all night.

The party started on Friday and by Saturday the money was gone, just the money to return home. We all were packing our stuff and preparing to leave when I told my brother I had more money but didn’t want to waste it with my friends so, as he was the younger, he helped me to lie my friends. We told them that he wasn’t feeling well after all the alcohol he drank last night and the we were going to leave later or until the next day. A girl friend of mine wanted to stay with us but I told her we will be ok.

My brother had no clue about what I wanted to do that extra night until it came. I bought some more beers and we drank them. We were kinda drunk when I told him the night was pretty hot and that I didn’t bring any pajamas. I asked him of he wouldn’t mind if I wore my bikini. I changed in front of him without saying a word, like it was the most common thing. Then I asked if he ever had seen a girl naked in real life and he said he didn’t, so I asked of he was a virgin, it was obvious he was a virgin but I had to ask. Then, to make the story short, I undressed myself and told him he could stare at my body and touch it if he wanted. We were a little drunk so it was pretty easy to start things.

He sat on my bed as I was lying there naked. He grabbed my breasts first soft but after a few seconds he starred to do it with pressure and pinching my nipples. It was so hot. I touched my clit and started to stimulate it until I came. I told him to get naked and he did so. His cock was big for his age. Maybe 7 inches long. I told him to fuck me and he didn’t even hesitate.

I was with my back on the bed, my legs spread and my brother on top of me, fucking me really good to be his first time. He kissed me and I liked it (I don’t like when my dad or my big bro kisses me on the mouth) my lil bro was a good kisser. So he was pounding me as we kissed and he grabbed my tits. He came after a few minutes. Like 10 or 15 minutes.

We waited another 15 minutes, time we spend talking about how good it was and he telling me how beautiful and sexy I am. He told me about how he would fantasied about being with a girl like me but not me. He told me I was his kind of girl and how he wanted someone like me with long dark hair, slim, brown skin, good sized tits and ass. As he told me that his cock grew again and I have him a blow job and sat on top of him. I ride him for maybe 20 minutes before he came for the second time but I didn’t stop riding him and I talked dirty to him, telling how much I liked my little brother’s big cock, and told him to fuck his sister and to grab my breasts and spank my ass. That kept his dick hard and I came after some minutes. We waited again and when his cock was hard again I went on 4 and he made me from behind. That felt so good I came easily 2 times on that pose. He spanked me a lot and I loved it. Then he told me he wanted to cum on my face and I agreed but he came just a few drops.

We slept and in the morning we did out again. And in the shower. And before leaving.

“Aunt” Wendee

I’m not much of a writer so bear with me. All my life my moms best friend wendee had been there for my family. She is someone that we have always been able to count on. It was 5 years ago that our relationship changed.

It had seemed like a normal day like any other. I went to school socialized and endured boring lectures. When suddenly during final period I had been called to the office. Nervously thinking I had done something wrong I was crushed to find that my dad had been in a car accident.

Everything was a haze as my mom picked me to take me to the hospital. For hours I paced wondering if he was going to be okay. Thankfully he would be just fine but have long recovery ahead of him. Mother refused to leave his side.

However I was sent home with Aunt Wendee so that I might calm down.

Finally calming down after dinner with Aunt Wendee. I went to the guest room and tried to lay down and rest. As the hours went by I tossed and turned. Eventually Wendee came in and thankfully was a source of great comfort both of us talking into the night with her reassurances.

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I had always found Wendee attractive. I mean who wouldnt? Long brown hair, full breasts and lets be honest a dump truck of an ass. She was a young man’s dream.

Over time I could smell the alcohol on her breath, and could feel her leaning in closer the longer we spoke. Before I could even think Wendee leaned in and kissed me with passionate abandon. Our tongues danced in each others mouths as my head spun with surprise. I could barely catch my breath as she pushed me onto the bed holding me down with one hand and unbuckling my pants with the other. 

Breath running ragged I watched her eyes fill with lust as she slowly started stroking me up and down. Being young and inexperienced my toes were already curling as I started leaking precum as her smooth perfectly manicured hands ran up and down my length. After what felt like an eternity and feeling on the brink of my limit. She stopped and allowed me to catch my breath and calm down.

Finally as she lifted her sundress she broke the silence and said “Are you sure?”

It was all I could do to meekly say “yes”

She braced herself against my chest as she lowered herself onto me. Feeling her warm velvety folds squeeze me I couldnt help but thank god that it Wendee who had made me a man. 

I couldn’t do much but hold on as she grinded her hips against me working my cock faster and faster into a rhythm. Gasping for air I could only focus on prolonging the pleasure as her DD’s hypnotically bounced along with her.

Finally I could take it no longer. My legs began to shake and tighten. Wendee sensing that I was at my limit slammed her hips down taking me as deep as she could. She held me down and kissed me as I released torrents of cum deeply into her. Gasping and exhausted I could only see her smiling face. As she kissed my cheek i faded into sleep.

*******************************************************************************************The next morning I woke up alone. Getting dressed I made way down to see her cooking breakfast with a smile on her face. As we ate we both agreed not speak about it and went on our way.

A couple of months later at the neighbor hood block party she announced to everyone that she was “FINALLY” pregnant. I could feel myself go as pale as a sheet as my mom and dad rushed up to congratulate her. 

Waiting for hours in the day I could feel myself in a nervous sweat. Eventually she found a moment to get us alone. She confirmed what I feared. The baby was indeed mine. Apparently she had wanted to start a family for a long time but couldn’t. So that night with me she drank some liquid courage and took the plunge. She assured me she wouldnt tell anyone I was the father and that she didnt want anything from me. She was just happy to be a mother.

Well that’s it everyone. That’s how I lost my virginity and became a father of a bouncing baby boy all in one go.

soft & cute 💝